The Art of Finding Love: A Lawyer's Path to Lasting Love with Heidi Friedman
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Description
Heidi Friedman has built a powerful career over the past 30 years as a partner at Thompson Hine, where she leads in environmental law and co-chairs the firm’s ESG practice. But behind the legal accolades and leadership success was a different kind of ambition—finding real, lasting love.
In this episode of Branding Room Only, Paula sits down with Heidi to talk about her most personal project yet: her debut book, Love Lessons: 104 Dates and the Stories That Led Me to True Love. What started as a self-exploration turned into a decade-long journey filled with dating apps, therapist couches, personal growth, and one eventual "yes" that made it all worth it.
Together, Paula and Heidi explore how building a personal brand applies to both professional success and finding a life partner. They get real about dating after divorce, setting boundaries, therapy, vulnerability, and how authenticity and timing matter just as much in love as they do in leadership. Plus—yes—they dive into dating profile branding tips (because, of course!).
In This Episode, You'll Learn:
Why Heidi believes your personal brand should reflect your passions, values, and consistency
The story behind her 10-year dating journey—and what 104 dates taught her about self-worth
Why being ready and being authentic are prerequisites for love (and career success)
How to navigate the “branding” of dating apps—Paula shares her matchmaker secrets!
The role of therapy, caretaking, and community in shaping both personal growth and partnerships
How to think differently about failure, friendship, and “showing up” for your life
Chapters
1:12 – Heidi defines personal branding, describes herself, offers two favorite quotes, and reveals the song that energizes her
5:31 – Heidi’s upbringing, educational background, and career at Thompson Hine
9:00 – How Heidi built the ESG practice at Thompson Hine and established a consistent brand around an ever-changing topic
12:35 – How Love Lessons came about and why Heidi wanted to share her personal story so openly
16:07 – The significance of therapy in Heidi’s journey to finding love again
18:58 – Key lessons Heidi learned about love (and relationships overall) from her research
26:55 – What Heidi learned about herself in the process of going on 104 dates over 9+ years
29:30 – The importance of authenticity in dating profiles (and the weird date that Heidi remembers most vividly)
32:55 – Paula’s best practices and rules for dating and online profiles
37:59 – How Heidi knew that her husband Will was “the one” and how fortuitous opportunities can come even amid bad circumstances
46:39 – Advice for single/divorced people in or approaching midlife who are looking for love
52:19 – What Heidi likes to do for fun, won’t compromise on, and provides for others as part of her magic
Connect With Heidi Friedman
Heidi Friedman is a successful attorney and partner in a large law firm specializing in environmental law and ESG counseling. Love Lessons is her first book, but she has written regularly for Bloomberg, Law 360, and other publications about her professional life and her experiences as a female lawyer.
After 10 years of being single and going on 104 dates, Heidi found true love. She lives in Cleveland Heights, Ohio with her husband Will and a cur mix that they rescued named Felix. She has four children: two of which she birthed (Morgan (25) and Zach (21)) and two bonus kids (Max (27) and Ben (26). In her free time, she enjoys walking around Shaker Lakes and doing yoga and Pilates, and she and Will also love to travel, go on date nights, and spend time with friends.
Heidi Friedman | Instagram | Facebook | LinkedIn
Mentioned In The Art of Finding Love: A Lawyer's Path to Lasting Love with Heidi Friedman
Love Lessons: 104 Dates and the Stories that Led Me to True Love by Heidi B. Friedman: Amazon | Barnes & Noble
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Sponsor for this episode
This episode is brought to you by PGE Consulting Group LLC.
PGE Consulting Group LLC empowers individuals and organizations to lead with purpose, presence, and impact. Specializing in leadership development and personal branding, we offer keynotes, custom programming, consulting, and strategic advising—all designed to elevate influence and performance at every level.
Founded and led by Paula Edgar, our work centers on practical strategies that enhance professional development, strengthen workplace culture, and drive meaningful, measurable change.
To learn more about Paula and her services, go to www.paulaedgar.com or contact her at info@paulaedgar.com, and follow Paula Edgar and the PGE Consulting Group LLC on LinkedIn.
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Transcript
Paula Edgar: Welcome to the Branding Room Only podcast where we share career stories, strategies, and lessons learned on how industry leaders and influencers have built their personal brand. Now let's get started with the show.
Hi, all, it's Paula Edgar, your host of Branding Room Only and I'm very excited about the conversation I'm going to have with my guest today, Heidi Friedman. She's a partner at Thompson Hine in the environmental group and co-chairs the ESG practice.
She, however, is here to talk about her most recent work, a book she authored to share her personal story about life and love, Love Lessons: 104 Dates and the Stories That Led Me to True Love. It is her first book and it shares a 10-year journey going from a failed marriage to finding the one and everything in between, including building a law practice at a big law firm as a single mom. Heidi, I cannot wait to jump into this conversation. Welcome to the Branding Room.
Heidi Friedman: I am so happy to be here, Paula. You know I'm a huge fan. I've been able to see you speak all over and you always inspire me so I really feel honored to be with you today.
Paula Edgar: Well, it's a mutual fan club and I love those. Tell me, what does personal branding mean to you? How would you define it?
Heidi Friedman: I feel that a personal brand is if someone saw your picture, what would they think of? What's the first thing that comes to mind? That is when you're successful in branding, but I feel that it has to be something that you're passionate about and you really want the world to see you as a caretaker of whatever that is.
For me, it's certainly women in the law as well as supporting other parties and other individuals and historically underrepresented groups. Lost my words there for a second.
Paula Edgar: No, I love the way you mentioned this because I often will relate the experience I have when I drink Coca-Cola, which I love very much, in thinking about branding because when you see it, I know what I'm expecting. When I drink it, I know what I'm getting. When I'm finished, I feel sad because the experience is over.
I feel that way when it comes to branding, like what can you expect from someone based on your connection with them, what you heard, et cetera, and how it all comes together. Then consistency after that.
Heidi Friedman: Absolutely, consistency is so important.
Paula Edgar: 100%. Speaking of that, how would you describe yourself in three words or short phrases?
Heidi Friedman: That is very hard, but I would say authentic, collaborative, and connector.
Paula Edgar: Oh, I'm going to take the dealer's choice to also add a word of my own. I think you're a spark plug. Every time I'm around you, I feel better and there's not a lot of people I say that about.
Heidi Friedman: That made my week. That's so nice.
Paula Edgar: Oh, I'm adding that to it because it's my podcast.
Heidi Friedman: I like that. I might steal it. That's fantastic.
Paula Edgar: You're welcome to have it. Do you have a favorite quote?
Heidi Friedman: I have several. My very favorite quote is actually an oldie but a goodie, which is, “Be the change you want to see in the world.” I really feel that we have to make things happen, and I've always tried to be that person to make things happen.
But I also, if I can give you two, another thing I live by, and I talk to my kids about a lot, is, “Comparison is a thief of joy.” I think in today's social media world, and definitely, I learned through my love journey, if you're going to compare yourself to other people, it's going to prevent you in the UVU motto I try to live by and I really think it'll prevent you from having the joy you deserve to have.
Paula Edgar: So, so true. I love both of those because especially at a time such as this and whenever folks hear the podcast, it'll still be that time.
Heidi Friedman: Definitely, yes.
Paula Edgar: Yeah, we definitely need to be thinking about being the change. Then on the flip side, I always say, “I don't believe in competition.” I believe that our past is our past, that our story is our story and that looking at others for inspiration works but not for comparison.
Heidi Friedman: It's not pie. [inaudible] if you take a piece.
Paula Edgar: Now I'm hungry.
Heidi Friedman: I like cake better, but that's okay.
Paula Edgar: Same. Do you have a hype song? This is like a song that when they're going to get full Heidi going on the stage, it's going to be in front of the client, et cetera, what's playing in your head.
Heidi Friedman: I have to look up who sings this, but it's been my hype song. It actually was when I was a single mom, when the kids had something big, we played in the car and we'd sing at the top of our lungs and it's the best. It's "Fight Song" by Rachel Platten, and I didn't know who sang it, so I had to look it up. But it's still to this day when it comes on, I just feel this incredible energy to go out there and make it happen.
Paula Edgar: It's a good one. I think it might be the first time that one of my guests has said that one, so the mixtape is going to be real good. So I love to ask this question to everybody who I interview because I find that it gives me a little more context into what I'm seeing in front of me. So tell me, where did you grow up and how did that shape your brand?
Heidi Friedman: So I actually grew up in South Euclid, Ohio, which is a very small suburb in a very, very tiny house in a room I shared with my sister. I was the first person to go to graduate school in my core family or grandparents, all that kind of stuff. That was a big deal for me.
I put myself through college and law school. I grew up in an area where I would say it was a middle class, but maybe even somewhat a little lower middle class. Certainly had all my needs met in all of those things, but wasn't able to go away to summer camp like friends or things like that.
And so that's where my upbringing was. Interestingly, I never really got very far. I went to Ohio State for undergrad and then Case for grad school. I've sort of lived in Ohio in one way or another my whole life. It's actually my dream to eventually go someplace else, but so far it's been good to me.
Paula Edgar: I love that. You said you have one sibling?
Heidi Friedman: I have two siblings. One is actually 10 years younger. She slept in her own room because she was in a crib when we were in that house. But yes.
Paula Edgar: So then give me the story from you at Case or you at Ohio State where you want to go to and how that ended up being what your career journey was from there.
Heidi Friedman: I will tell you that my career journey is slightly boring, but you could also call me extremely loyal and dedicated.
Paula Edgar: And super focused.
Heidi Friedman: So I basically graduated from Case in ‘95. But I spent my first summer working for a divorce lawyer because I thought I wanted to be a divorce lawyer, which is really interesting as things came upon in my life with my own divorce and everything. But I couldn't stand watching two people fight over a chair.
So I decided I needed corporate law. This is not for me. I worked at where I'm still at, Thompson Hine as a summer associate back in 1994, and then I got the job offer. I've been there now practicing for 30 years.
So I have had offers and thought about things, but it really has been the perfect fit, a really good platform for me. They've been really good to me through some really hard times, so a lot of stability. I've been able to build a fantastic practice. I have a work family that I adore.
So it's been a great place, even though I don't have 10 moves to share with you that would probably make for a much more exciting podcast.
Paula Edgar: I mean, it actually, and when I was thinking about the stories, the questions in relation to your story, I like this part about it because when I've seen you talk about your experience at the firm, you have spoken about it in that you've gotten support, you've been able to build, you've been able to innovate, and you've been able to make great friends. I think that that's an important thing that is often lost in some spaces because we don't have communities that may be like that.
So that's wonderful that you are able to have some place that supports your growth and when you have challenges and when you are flourishing. I think that that's fantastic. Good, boring or not, I want to know. But tell me this, because one of the things I heard you say during a fireside, I think it was a fireside chat that you did, you talked about being innovative and kind of seeing things and wanted to start something new. That was what you did at Thompson Hine in terms of building the ESG practice there.
How do you figure out your personal brand around something that is new and engaging and always shifting? How do you maintain the consistency that we talked about that is of building a personal brand there?
Heidi Friedman: Sure, I'll use the ESG as an example because you use this. I went back to University of California, Berkeley, got my ESG certificate several years ago because I realized that I've been doing the E of ESG, which is environmental sustainability for 30 years.
But it really has become a much broader umbrella and a lot of things fall underneath there. I had a lot of interest from clients around this topic so I wanted to become much more of an expert. I knew we could add value.
I loved it so much because my normal practice, although I adore what I do, I basically national counsel to large companies and I counsel them on environmental matters, many of which happened 30 years ago. We're kind of looking backwards, cleaning things up, et cetera. ESG is very much looking forward, adding value.
So I loved that dichotomy and the ability to do both of those things. Then I really felt in order to build my brand, I think the first year we had in ESG practice, I spoke on ESG 40 times and I am not exaggerating. I accepted every offer someone gave me.
I mean, the good news was it was so new at the time I really didn't have to redo my slides. It wasn't that heavy on the lift, and I wrote a bunch of articles. I did one for Bloomberg and one for Law 360 and all of that.
Then we did two other things that I thought were really interesting that helped with our branding. One is we did a survey of our clients and we asked them what they were doing about ESG and then did a report on that and we hosted a roundtable around ESG and got a lot of clients to participate. So it was really immersing yourself in this space in a way that you become a leader and I will honestly say I spent a ton of time reading and learning and teaching myself.
The one thing I believe in on brand more than anything else is being authentic. If you are trying to be someone else or be like somebody else or something like that, it won't work.
So I felt that if I was going to put myself out there as an ESG expert, or at least as someone who was working in the space and had some benchmarking—because I really can't be an expert so new—that I really wanted to have the experience and learn it. That's how I developed my brand around that innovative topic, which has been a lot of fun.
Paula Edgar: I mean, you, without me feeding you the answers gave me the right ones, again, it's right because it's yours, but when I think about building a brand and innovation and how you kind of take something new, it is that. It's saying, I want to make sure I understand this. I understand the framework. I also want to continue learning, like the growth mindset piece of it.
And then I need to amplify as people need to be able to hear and know me as a, at least developing expert, so writing and on speaking. Check, check, check, check, check, check, oh, thanks. I love this.
Heidi Friedman: I learned a lot from someone great.
Paula Edgar: I love it, I love it, I love it. Okay, so tell me this. I want to jump into the book.
Heidi Friedman: Okay, I love talking about the book.
Paula Edgar: Yes, and I'm excited for this conversation. Your new book, let's say one more time, Love Lessons: 104 Dates and the Stories That Led Me to True Love, is super personal.
Heidi Friedman: It is super personal. It's a little bit of a tell-all memoir, actually.
Paula Edgar: What made you decide that you're going to share your story so openly?
Heidi Friedman: It was not an easy decision. I definitely let my husband and my four kids all read it first to make sure everyone was comfortable. But it really was an interesting trajectory with the book, because the first part of the book actually came about when I was turning 40. At the time I was traveling all over. We were doing a big talk tour case. I was doing depos of epidemiologists. I mean, I was just all over the place.
So I would take the interviews of friends who I asked, “How did you know you were in love?” Because I was truly convinced I did not know what true love was. I decided I just don't know what it feels like. I'm a black-and-white, it has to be concrete. You can't give me a gray field. I need to know something very clear. I was looking for the answer.
So I found all these themes and I wrote about eight chapters originally with each of these themes. Then I parked it on my desktop and I truly forgot about it for about 10 or 12 years. Then I found it and I was like, “Oh my God.” In fact, the original title was called Embracing the Gray because I thought it was so gray. But when I met my husband, it was completely clear as day. So then I was like, "Okay, well, that doesn't ring true. We have to rename it."
Then I just started, "Oh, it'd be fun to write." And then a friend, Heather [inaudible], mentioned I should talk to her publisher who sent me to someone. I don't know. All of a sudden, it was a book. I just felt that my team will probably tell you that I'm an oversharer on some level because I want people to share about themselves. I think if we come into work with our clients, with our teams, and again, we're authentic and we're real people, it just builds a level of trust among the team with the clients that I really value.
So I feel like the more you know about me, the better it is on some level. I just felt it's true, I said this to you before, I truly feel like we're at a time where we need more love in the world. I really feel that as an independent woman, I am RBG fanatic, independent woman, I could do anything I put my mind to—I'm convinced of that. But my life is so much fuller because of my husband. I have so much more joy. I just feel that it's a really good message that you can be independent and successful with the right person. That adds so much more to your life than just work, work, work.
So it was combining those messages. Then I would say at the end of the day, I wrote it for my four kids, so they would not make some of the same mistakes that I made. I really want them to find their true person that makes them a better person.
Paula Edgar: Oh, I love that. I have so many things I want to say about what you just said. One of my favorite things about the podcast is like, I'm always like, “Here are the things I'm going to ask you.” Then I'm like, but I'm just going to—we're going to go with the conversation and let the spirit move me.
Heidi Friedman: I'm game for anything.
Paula Edgar: So a couple of things. Weren't you scared? I've been married 22 years. I remember when I got married, I was like, “I only ever want to do this one time. I don't want to bear my soul and figure out all the things with somebody else.” You had a divorce. That comes with a lot. Talk to me about what work you had to do to get yourself from the loss of divorce to being open.
Heidi Friedman: Failure.
Paula Edgar: Yeah. I don't think of it as failure. I don't—I think that if it's not your person, it's not your person. I think that it's a loss because you had expectations, but—
Heidi Friedman: Ooh, that's a good twist. I like that. But failure is okay too because you learn from it, so I'm okay. I do talk about this quite a bit in the book. I'm a huge fan of therapy. I've had a ton of therapy. My kids have had a ton of therapy. I probably have put my therapist, she now has a home on Martha's Vineyard or something. I'm sure I've paid for most of that.
But at the end of the day, I really had to figure out more about who I am. For some reason, when I was younger, and I still haven't figured this out completely, but I did realize that I did not think of myself as worthy of the love that I have now, for whatever reason. I really had to build my self-confidence as well as see what works with others and see what worked for me and did not work for me. I needed someone to value my career as much as I did. I needed someone to value my kids as much as I did.
But it was scary as hell. Are you kidding? I mean, I'll never forget my first date. It was so scary. Then I ended up reconnecting with a longtime camp friend from years ago because that felt a lot safer. But as I continued and I progressed, it was always a little bit scary. I feel like every time you put yourself out there, whether it's for work or for life, it's a little scary, but you have to do it or you will not have the joy that could come with it. So I really feel like I say to my kids all the time, half of it is just showing up or just showing up is a huge part of your success in your future.
Paula Edgar: Oh, yes. Carla Harris, who I recently interviewed in my podcast, she says, "Fear can't be a part of your success strategy."
Heidi Friedman: Right. There were so many times I wanted to lay in my bed and back then it was probably watching The Bachelorette, now it would be watching Real Housewives, would be the equivalent. But you just do nothing because it just felt comfortable. But I knew that there was happiness out there for me, and I felt that I deserved it, and I wanted to find it.
Paula Edgar: To your point about the first part of the book being something—well, I just love the concept because it's so authentically lawyerly. Like, I have a question, I need to figure out the answer, so I'm going to research interviews. What were some of the profound lessons that you learned about love from that process?
Heidi Friedman: So Law 360 interviewed me last week, and they were laughing at that too because I said I'm a total data geek. When I need to figure out something, I will research it and figure it out. I need to know the answer. There's always an answer. I decided if I took my legal and analytical skills and I talked to enough people, I could figure it out.
The cool thing about that was I did realize, and I think I talked at the end of the day to about 50 people, I wouldn't say 50 couples, because sometimes I talked to both people if I was close to both of them, but sometimes I was only close to the wife or just close to the husband because it was a law field friend. I didn't always talk to the whole couple. There were about 50 people, and no one's answer was exactly alike. Everyone used different words. But when I took my analytical mind and read everything, these themes just popped up.
So I felt like it was almost a law school exam where you're reading a story and have to figure out what issues are in there. It was very much that kind of process. I do think that my training helps me. Sometimes I'm not sure it helps me in my life that much because I tend to be a serial overanalyzer, but it did help me in that situation.
Paula Edgar: Yeah, so tell me, what stood out for you about those themes? What are some of the things that came up about love? Because I agree with you, I think that we do need more love, just in general.
Heidi Friedman: We do need more love. I mean, and they kind of apply to all relationships. It's not necessarily just a love relationship. It was interesting, I talked to same-sex couples and things like that, and it was still the same theme. I love that—like love is love. It really reinforced that. That was fun too.
I would say two of my favorite things are that that person makes you your best self. I truly believe Will has 100% made me my best self. He has taught me so much. He supports me endlessly, it's just fantastic. That's probably the one thing I ask my kids whenever they're dating someone—"Is that person making you your best self, or are you catering to that person? Is that person draining you in any way?"
The same should be true of friendships. It should be the same way. I'm going to be 55 next month. As I get older, I'm looking at my friendships through the same landscape to say, "Okay, do I weed people out that might not necessarily fit that bill?"
Paula Edgar: Oh, yes, and I'm not going to let that pass without making sure that my audience heard that because, while I love that this is about relationships, I think that the most enduring relationships that we have are with our friends. I have friends from when I was in elementary school.
Heidi Friedman: Me too.
Paula Edgar: But having as a part of the process to look and see, "Does this still serve me?" is a really, really, really important thing because I know that once I have—speaking of branding—when I have shed some folks who were more draining to me, and again, I don't mean to be like, "Okay, bye, off with your head," but to say that you're no longer in the starting five, you're on the bench until you don’t necessarily get priority in the same way, everything else started to lift up and flourish. You don't realize they're pulling you down.
Heidi Friedman: 100%. We always feel like we owe certain people certain things. I'm just sort of at the point where I'm starting to get over all of that. I think that it's important to have as much joy and happiness as you can by surrounding yourself with people that lift you up. That was super critical. I couldn't agree more.
The other one that I think really stood out for me was the fact that these folks who had really successful relationships took turns taking care of each other. I am such a caretaker. If I find out anyone's anything, I have food there. I really love caretaking. I'm not sure if it's the Jewish mama in me, I'm not sure what it is, but I love it. So I would say I think I have found, after lots of therapy, I think I've dated people historically that I had to take care of. It was a very bad dynamic.
What really enthralled me is that these people really took turns caring for each other, just like a really good friend. If a friend's just always asking you for things, it's draining. But if sometimes you're low, she's high. My best friend, we take turns with our issues for the most part. We can help each other on occasion and you rise up together. That's been really important.
My therapist told me a long time ago, it's almost like, when something bad happens, picture a wave coming over you and you want someone to pick you up and pull you out of it. If every time you're the one having to save the person with the wave, you're just going to be tired and it's just not going to work. That was my other meaningful love lesson that I learned.
Paula Edgar: That is a great analogy, that wave thing, because I can imagine myself—because I also too, I'm a helper.
Heidi Friedman: Right, exactly.
Paula Edgar: I don't consider myself a caretaker, actually, don’t at all, but I'm a helper, so I want to fix things for folks. I do think that people are often set to take advantage or not sort of modulate that so that you will always end up on the side of, "Okay, well, no one is doing that for me or not in the same way."
So as I was skimming through the book, something that I saw made me smile because I had a similar experience. You mentioned in the book that you went to the Wailing Wall in Israel and you put a note saying that you wanted true love. When I went to Israel, I said, "I want love forever."
Heidi Friedman: Love that.
Paula Edgar: It was literally a very spiritual trip for me. But my viewers know, my listeners know that when I lost my mother, I was in my 20s and my parents had been married for over two decades. My mother had raised me from when I was three years old. She was my primary mother, but not my biological mother.
I remember thinking, my dad has lost that love, and I never want to lose the love that I have. I walked away, and I was like, "I should have asked for money." But in the end, the first part of what you said about recognizing that the person makes you better is so—like, I could do nothing that I do without—and again, I probably could do it, but not in the same way that I do it. People are like, "Oh, Paula, you're so free." I'm like, "Yeah, because I know that things are being taken care of behind the scenes, or that I'm supported in X-way all the time." And that is such a huge thing, such a huge thing.
Heidi Friedman: Amen, sister. I mean, I think maybe I even value it more now because I didn't have it before. Once you have it, it really becomes something that you treasure and take such good care of as well. But I am also a helper. Olivia Pope was like my idol because she could fix everything. I am a serial fixer. I got lots of problems.
Paula Edgar: So when you were doing your own work and going on these dates—which just the whole concept of it, I'm like, “Oh my God.” What are some of the things you experienced or learned about yourself in that process of going through 104 dates? That's just wild to me. Tell me what you learned.
Heidi Friedman: Okay, so it wasn't 104 people, don't be alarmed.
Paula Edgar: All good.
Heidi Friedman: It was probably like, I was trying to figure out exactly, I think it was 55 people, because I didn't keep—one time I went through it, I don't even know exactly. But I think it was about 55 people if I'm remembering, because I did date three different people. One I dated for six months, and so we went out like 20-some times. It wasn't 104 guys. That being said, it was a lot of guys.
Paula Edgar: I was going to say like—
Heidi Friedman: It was a lot of Match.com, JDate, Lunchdate, all of the things. I would say the one thing I watched in myself throughout the nine and a half years is I became stronger and stronger in understanding what I needed in my life and what I wouldn't settle for in my life that I may not have been as diligent about previously.
By the time I met Will, I had really, I think, a pretty clear vision of what I needed my life to look like to let a partner into it by that time. I mean, some of these dates were 10 minutes. I was like, "Out." You know, it's really good to have little kids so, “My daughter called. I’m so sorry, I gotta go,” you know, that kind of thing.
So it was great in terms of that process. I mean, I did meet some fun people who I keep in touch with—it just wasn't a love connection, but I keep in touch with them. One guy I went out with is now a client, which was a very long, weird story, but not on purpose. You never know.
But I would just definitely say that it was a journey in self-confidence because I didn't have that. While it became frustrating at times, I became more committed to, "If I have to be alone, I have to be alone, but I'm not settling," which is really hard when you're alone raising two kids. But it was definitely where I was right before I met my husband—sort of over the whole thing, which was interesting. Then he came along through a really good friend, and it was such a gift.
Paula Edgar: So I need to pull this apart. There are a couple of things I need to—so one thing I will say is, when I saw you post about this on LinkedIn, I was like, “I have to talk to her.” Because only some people know that my secret skill set is Love Coach Paula.
Heidi Friedman: Really?
Paula Edgar: So people in my sphere—I have two couples, a couple of babies, people who I have put together. I am often very much passionate—I'll say that. My friends who listen to this, they're going to be like, "Girl, I'm obsessed," but about how people set up their online profiles for dating and the best practices around it—because it's branding.
Heidi Friedman: It is branding.
Paula Edgar: It is branding.
Heidi Friedman: But at some level, what I would worry about—I'm interested in what you think about this. Not that I'm interviewing you, but I'm super interested in this because that was the one time in my life that I felt like I wasn't completely authentic.
Which I did sort of abandon all of that later, and I just sort of went on fix-ups. I was super done with the apps. But when I was on the apps, that was the one time I felt that I was not truly authentic. What do you think of that?
Paula Edgar: I think that's why it didn't work. What I see often is people are trying to put what they think people will like versus who they are and let the people find them. We talk about authenticity. I want people to be like, "I like toast on Thursday." Like specific things and be like, "You know what? Take what you get, what you're getting, don't get upset."
Heidi Friedman: That's how you guys said it to my kid's [inaudible].
Paula Edgar: Exactly. But what happens is that you put yourself out there as this thing that you think they want, and then that's who they expect.
Heidi Friedman: Yeah.
Paula Edgar: And then you're like, "Oh, just kidding."
Heidi Friedman: Right. I was borderline authentic. I mean, the guys were not. I mean, I can't tell you how many times I showed up, and the guy wasn't even looking like remotely like that picture. Things were awry, and he wasn't really divorced, and it was a mess.
I mean, my favorite one—I don't know if you got to this one yet—my favorite one is, I did meet somebody on Match, and I always did my due diligence as a lawyer. We emailed back and forth and all of the things. I Googled him to make sure he wasn't bankrupt or a serial killer, all of that. Check the court docket.
So I go, five minutes into this date, it's weird because I don't remember all of them this clearly, but I literally remember what he was wearing, what he looked like. He hands me this cease and desist order from Pepsi because he's, I think, either marketing or somehow he's working with Gatorade as a distributor, I guess it was, out of his garage.
He was looking for legal advice from me on the cease and desist order. It was the craziest thing I've ever seen. I did leave after five minutes, but it was just the "My kids are calling, I've got to go." Isn't that funny?
Paula Edgar: That is a hot mess. I've had girlfriends go through the years who have been single. I have heard wild stuff about dating. It's some of the people who I have connected with.
I have a couple of best practices that I want to share on the podcast because I was like, "Oh, I'm excited because I get to talk about this," and I want to hear all this stuff out. One is, you have to have a picture that is a good picture of just your face. Then you have to have a picture that shows some skin and body.
And here's why—because at its core, we are animals. So what we look at is attraction. And you don't want somebody to be like, "Okay, I saw your face, that's fine," and I see [inaudible], and then everything else is not what they want. Because it's not like you can hide it. They're going to find out.
Heidi Friedman: Oh no, that was the scariest part, yes.
Paula Edgar: Right, so that is one.
Heidi Friedman: I did follow that rule, so so far so good, keep going.
Paula Edgar: And the skin part is important. The second piece when it comes to pictures is, don't have pictures where you've cropped other people out because there are a ton of pictures where you see somebody's hand on the shoulder and then the person is gone. Or like, trust me, I've seen some egregious cutting up of people. So then the immediate question is, who was that? Why are they cropped out? Why did you use this picture? I'm looking at your judgment. A lot of things.
I would say, wear bright colors. Not in all the pictures, but at least in one. Photography and pictures don’t give context, it's just the picture so I have to make up a story in my head. I'm saying, “You chose this.” If this picture is terrible, then that is—I'm questioning. I don't trust you. The person is not going to be able to trust your judgment based on how you have done this. Okay, that's number one.
Heidi Friedman: I love the matchmaker. I like this, this is a whole new side of you I've not seen, we can collab.
Paula Edgar: That's what I'm saying, I love it, I love it. My second thing is, in all the questions that they ask you to answer, depending on the app, just tell your truth. Not what you think people want to hear, just answer the question. Do you want kids? Maybe? No, it's yes or no. I want to know. Because the thing is, is that some people, the questions are their pivot point.
So if you are wishy-washy, it's not fair. Again, you could be undecided, and that’s a fair point. However, usually, depending on where you are in your age range, you know where you want to go or you don’t know where you want to go. To be unclear is unfair to folks who are looking at you.
My third thing, my third rule is, I don't believe you should have to spend over $50 on the first date, ever. But I do believe the other person should pay. Now you can email me all you want, I'm not changing my mind.
The point is this: I do believe in chivalry. I do believe in that you have to put a little investment into things that you do. I do understand, and I have both a son and a daughter, and I will teach my son, "You have a $50 maximum on a date."
That's true. Why should you be spending hundreds of dollars on somebody you don't know? On the other hand, I will also tell my daughter—and she already knows this, she's a college student—I tell her, "Always be prepared to pay, but don’t expect to pay."
And look, I don’t want—so it’s funny because as a married person, I pay for all the meals. People are always like, "Oh," like they put the bill in front of somebody else, and I’m like, "No, I’m paying for it." It is what it is.
But those are some things I think that help you to just show up in an authentic space. I've seen all these memes where people are like, "Oh, I can't believe you didn't take me to the steakhouse on my first date." I'm like, "Are you lucky if I take you to the library on my first date?"
Heidi Friedman: That's why I always recommend, just go have a drink. If you get a cocktail, if you don’t drink, one drink—that’s all, keep your commitment small.
Paula Edgar: I love that. I love that.
Heidi Friedman: Yes. It has to be. I did do that. I almost never—in fact, when I went out with my husband, we were just meeting for a drink, which turned into dinner, which turned into hanging out for three hours.
But normally, I always made it very clear that I only had a certain amount of time, but I could grab a drink, because I do think that that protects you a little bit from getting stuck in a really bad situation.
Paula Edgar: Oh yeah. Oh, that's another sub-rule. Just always be prepared to say, "I don’t think this is working, I have to go."
Heidi Friedman: Yes.
Paula Edgar: Whether you say, "My kids are calling," or whatever—always have an out point. One of my girlfriends is 20 minutes in, I need a call, and depending on what I say on that call, you know whether it needed to be emergent or if everything was fine. She'd be like, "What? Oh my gosh, I can’t believe that happened."
And two times she did it, and I was like, "I don’t remember what the keyword is. I don’t remember what she’s supposed to say. Is it an emergency now?" And she was like, "No, no, no, it’s fine." And I was like, "Okay, girl, I need a better script. Tell me what I have to say." Anyway, moving back into this, can you tell me what was it about your husband that made you know he was the one?
Heidi Friedman: That’s actually an interesting question that I’m wondering if anyone has asked me before, Paula. I will honestly tell you it was more of a feeling than a thing, which is anti-Heidi, anti-lawyer, anti-research, all of the things. We just connected. I talk about this in the book—you can’t fit a square peg in a round hole, or whatever the saying is. You can’t force it. If you're forcing it, it’s not right. I had to say that to one of my kids who was dating someone, and it did not work out. Forcing it does not work.
So it was so easy, and I felt—to your point—like I could show up as my authentic self. I felt like he embraced my crazy. We all have our crazy. He embraced the crazy pretty quickly. It was just this mutual respect.
He had a lot of sophistication. He was professional. It was the whole package. He was adorable—that helped. But it was more of this feeling than a thing. I was saying—I think I explained this in the book a little bit—that I truly believe in the concept of trusting your gut. I would say that’s the other thing I learned over my 10-year process.
I did not trust my gut. I’ve made some decisions in my life where my gut was saying one thing, and I felt like I could not do that thing or shouldn’t be doing that thing, but I did it anyway.
My gut got sharper and sharper and sharper as I got older, went through the process, had more dates—all of the things. Then I felt like it was really sharp at the end, where it gave me the information I needed. I'm telling you, I think I almost knew on my first date. I knew for sure by my third date. I talk about this in the book too.
I had little kids, so I had not introduced any of these 50-some guys to my kids. No one. That was my rule. They’re not dating my kids. This is not a playdate. We are just dating me. We left it at that. But Will entered my kids’ lives—it took a little bit. It was like six weeks or whatever, but it was pretty quick. I was very sure, which felt good.
Paula Edgar: So, there's a theme that's running through some of the things that you said that I want to pull out, because I think this is probably the most challenging piece of talking about love. It's this: It is, you can have all of the strategy that you want, you can do all of the things, but I do believe there's a spiritual kind of magic in the people who I know who are deeply in love, the universe conspired to bring them to that space.
So when you said, "I knew this was going to be my last date, and you were done," I was like, everybody—and then God was like, "Now I'm ready. Why don't you finish doing all of that? Now I'm going to bring you the person." With my not-scientific research, it's always been that. That being said, I think, I want you all to still listen, that you need to make sure you are ready.
Heidi Friedman: 100%. Ready is so important. I have a chapter that's all about luck because I do think there's luck in love. I do think it's a lot about timing. A crazy story, a quick story about my husband. He was living in Indiana and he was working for Duke Realty, which is a big, huge real estate portfolio. He had a huge job, and the 2009 market crash came, and he lost his job.
He was devastated. He was raising two kids, he was married at the time. It was just a complete disaster for him. That led him to moving to Cleveland to become the CEO of the board here, which happened, I think, two years after that in 2011.
And if that horrible thing did not happen, he would have never come to Cleveland, would have never met my friend Ann, and who knows if we would be together. It is really, "One door closes, another opens." You just don't know sometimes.
And I do feel that you have to be very ready. But I also feel like you have to give a little bit up to the universe, but you have to put yourself out there. I mean, that's really the point. You have to talk to people outside your circle. You have to do all the things and let the luck happen.
Paula Edgar: I have to share my quick love story because I think this is important when you talk about something bad happening. My mother was one of the victims in September 11th. When she died, obviously, I was devastated. My whole family was devastated. I came back to New York from there. I was living in California.
I dated my husband when I was 14 years old. Quotation mark "dating"—like, what does that even—what do you even do when you're 14? It is what it is. But I hadn't spoken to him for a decade.
Then he saw in the newspaper that my mother had been killed and reached out to his cousin, who had been my best friend, to say, "If she needs anybody to talk to, tell her she can talk to me." I have spoken to him every single day since then.
Heidi Friedman: I knew that about your mom, but I didn't know that that was the genesis. Wow.
Paula Edgar: Yes, yes. I would say my mother gave him back to me. It is a powerful thing. That's why I was saying like, it's a magical thing. Because at first, when we got back together, I was like, "Well, this will be fun for a little while."
Heidi Friedman: There you have it 22 years later.
Paula Edgar: You know. Exactly. I'm like—and that's the thing, is that we are still having fun 22 years later. Another quick thing, we went to therapy before we got married to just solidify, figure out, do some things. I recommend it as a best practice.
But one of the things that the therapist said—and it was important that somebody recommended I get a male therapist, so we got a male therapist to be our marriage counselor. He said, "Every morning, wake up and be grateful for the person you're with, even if they got on your nerves the day before." I got to tell you, that is key. Because I'm like, "I love my husband. I love my husband. Could you please do the laundry?"
Heidi Friedman: Like, a little give and take.
Paula Edgar: But it's a reminder of the butterfly feeling that you get from the person who you love. When people talk about the folks who they love, I love these conversations, they smile. When you talk about your husband, you're just lit up.
Heidi Friedman: Right, that was my favorite part about interviewing people. I think they don't get asked that question very often, and they just lit up. It was so funny, I was at a work meeting, IEDC actually, last week, and we were at this big table. One of my really good friends is dating somebody post-divorce. He's never been married.
I spent half the night listening to their story and how they met, and convincing him he should ask her to marry him later the next day. We'll see what happens with that. But I just still get fascinated by how people are brought together. I love love stories. I don't know, I love love. It sounds super cheesy, but I do.
Paula Edgar: But it's so true. I like that in the book, you also talk about the sort of science of it, the science of what we need as human beings. I studied anthropology as an undergraduate student. I know very deeply that human touch is an important part of how we navigate the world, to be able to actually be embraced and held as a part of what makes you thrive.
So my recommendation to single people is even if you don't have somebody to be with, like make sure—assuming you are able to—you get somebody to touch you every week, like every other week or every month, whatever it is, like a masseuse, or getting your nails done, just the human contact is a part of how we love each other. So I was not going to let you go off of this without bringing it up. We don't have to talk about it, but I just have to let y'all know there's a chapter on sex, y'all.
Heidi Friedman: It's not super—
Paula Edgar: I don't care. It's in there.
Heidi Friedman: Okay, there is, I will admit.
Paula Edgar: It's a selling point, I'm letting y'all know that.
Heidi Friedman: We won't leave it at that though.
Paula Edgar: No, right, that is exactly what I'm going to say because I do think it is important to remember all of the different aspects of relationships and that is all I want to say.
Heidi Friedman: 1000%.
Paula Edgar: You should read it for all of the things, including that. You were already a professional woman in the space when you were a college student, you were a professional woman when you were on this second love journey.
There are a lot of people who are in this space who are approaching midlife or in midlife who have lost love or are still looking for love. Any advice for them from what you have learned and what you have experienced?
Heidi Friedman: Absolutely. Two things. I've probably in the last three days had five emails or LinkedIn messages from women who are single moms and divorced and looking for love and saw the book and are relating, and oh my god, it just made me elated that I touched a chord and that's my dream, is to help these people.
But I have sort of become the divorce coach around Cleveland. I think it's probably because I am connected to a lot of people. I did get divorced when I was in my 30s before everybody else. I've certainly come out the other side.
So I tend to meet with women when they're at, what I say is, the very bottom of a very steep hill. For whatever reason, they decide that marriage wasn't working, and they have to climb that hill, and it's really hard to see down the other side.
So I do try to give both very practical advice, like divorce lawyers, what's going to happen, the kind of substantive specifics. But I also say it's a time for you to step back and just focus on yourself and your family and your profession in a way without the noise.
One of the things I did, for example, when I got divorced, I took myself off all these boards. I loved being on boards, nonprofit boards, and things like that. I just took a step back and I decided, "Oh, they'll still be here when I'm ready to step back on." And they sure were. It was great.
And then I always say—this is something I just told one of my kids yesterday—I think you need to look at the next step, not the whole staircase. Because sometimes I love that visual, and then sometimes you got to sit your ass on that step and stay there for a minute. You don't need to climb the steps or the ladder or whatever. There's always this visual of women climbing ladders in heels and stuff.
Paula Edgar: Yes, holding bags.
Heidi Friedman: Put your fingers on and sit on the step for a minute to start. You don't need to keep going all the time. I actually made the choice at my firm to stay a non-equity partner for a number of years because of a variety of reasons. But I just needed that less pressure.
I went on a flex schedule a little, but I did a couple of things that made my life more bearable. I'm still able to come back and be an equity partner and have a big practice. I figured out how to do it. I mean, you can't do it all. It's just impossible.
I think RBG said, "You can do it all, just not at the same time." So you just have to make really important strategic choices and it's not a marathon. You know, it is a marathon. It's not a race. Is that what it is?
Paula Edgar: I'm not running no matter what, but I understand.
Heidi Friedman: I got all my analogies mixed up today.
Paula Edgar: Understood. I’m like, whatever it is, I know I'm not running, but I get it. I believe very deeply in something I would often say, which is shed to get things, to get the things, get rid of things, to get the things, because often I think the state—and this is a lot of people just general, it's not just a gender thing, but that women often take on so much and understand how that weighs. We're not socialized generally from a gender perspective to prioritize ourselves.
So when you said in terms of your advice too, you have to put yourself out there, that is such a key point because people are like, "The person will fall in front of me. They will trip on a stone in front of me and into my arms."
Heidi Friedman: That won't happen with a client or a boyfriend. I promise you.
Paula Edgar: Exactly. I'm like, “I mean, you probably need to be outside at least to even get somebody.” So, yeah, one takeaway, and I believe this aligning with love, romance, relationships, and also branding, is that you have to put yourself out there.
That you have to have people have the understanding of who you are and how you add value in order to love you. That means, to your point, in work and in love and all of the other pieces. I kind of love, love, love that alignment.
I forgot that I wrote a note down and I don't want to forget that I need to come back to the fact that you actually ran the people you were dating through to see if there were any like—let me just pull up all of it. They have put it forward. I love that.
Heidi Friedman: I mean, listen, I'm a lawyer, I do my due diligence. I did end up going on one date. It was very odd, and listen, we all have hard times, but I think he was either bankrupt or involved in litigation or something I figured out afterwards. After that, I'm like, "Okay, I'm checking court records before."
And part of it is, if someone's not divorced, it won't—you know what I mean? They say they are, that's an interesting thing as well. It's a protective mechanism. I also say, sometimes you just have to follow your heart. I do believe that you need to be careful though and it will—being out there will help you make it happen.
Paula Edgar: Agreed, agreed, agreed, agreed, agreed. I knew that this was going to go by quickly. That is the nature of all of the things. But I really, really love this conversation. Tell me what you do for fun. What is the fun stuff?
Heidi Friedman: For fun, I love yoga. Actually, yoga is where I met my husband, not because he was a yogi, but because I have a crew at yoga that became really good friends and one of them, who I hardly knew that well at the time, was the one that fixed me up.
So Pilates, all of that stuff. I love travel. I love walking around Shaker Lakes here in Cleveland with my husband. We only have one joint baby, and his name is Felix. Felix Friedman, he's a cur that we adopted, and we are obsessed with him.
I'm now buying him sweaters and things because I have no kids to take care of—see the caretaker thing. I'm taking care of the dog. I love that. I would say the one thing that brings me more joy—if you put Will aside, because being with him brings me the most joy—is my girlfriends.
I just love getting together, having a glass of wine, and just being with my friends. I love your spark plug because there's probably a handful of women that are literally like my spark plug.
They give me energy, and when I'm with them, I come back feeling so much better than I did before. That really is what I love to do other than being with Will, probably the most.
Paula Edgar: I kind of love that you brought that together. The fact—I obviously haven't read that part of the book yet, about meeting in yoga. But one of my best practices in terms of dating and finding your person is to tell your people that you're looking for your person.
Heidi Friedman: 150% and you have to join things. So my oldest just moved to a new part of California. I said, "You need to join clubs." So he joined the running club, the scuba club, all of these things. He was so excited to tell me that he was taking my advice. It was fantastic.
So it really is important that you'll never know. Like me, even if you don't meet your person while doing that thing, I met my person through that thing. So it really is important to go beyond where your normal—sorry, if you're in your normal—I must say it's like a bunch of round circles, and the broader it gets, the better chances you have. The narrower you are, you can see what happens.
Paula Edgar: Yes, and be vulnerable and say, "I'm letting you know I'm looking for someone," because you then make the universe start to do what it needs to do, and you make them understand the assignment. Now they're looking for you.
Heidi Friedman: People love to fix people up. I get a huge thrill when someone asks me. It's fantastic. I mean, if I see you at a cocktail party, you're single, I'm going to ask if you're on the apps, what are you doing? How can I help? Who do I know? That whole thing.
Paula Edgar: Exactly. Okay. On my podcast, I ask everybody the same two questions. One is this: What is the authentic aspect of your personal brand that you will never compromise on?
Heidi Friedman: It's an interesting thing right now because I would say inclusion and for women and other historically underrepresented groups. The world's under a lot of pressure right now to push DEI aside. That is, in my bones, part of who I am. I've spent my entire 30 years doing things to make sure that those individuals can have success in law and life, and I'm not giving that up.
Paula Edgar: I love that. So Branding Room Only is a play on the term standing room only because I am clever. What is that piece of Heidi, that magic about you, that would have everybody in a room, packed, no seats in the house, only standing room to experience about you?
Heidi Friedman: I do think I am the ultimate connector. Is that an okay answer? I don't know if that's what you're looking for. I certainly wouldn't be doing a dramatic read of my book or something. I don't think that that would bring a crowd.
But, for example, I did a pop-up at yoga this weekend with my book, and this yogi friend was selling her vegan cookies. She just started making them, and by the time we were gone, I had connected her to my dear friend down the street who owns a coffee shop, and now she's going to have her vegan cookies. I just love that, though. Nothing makes me happier, and I try to do that all the time. That's really where I find my joy.
Paula Edgar: Well, the answer is right because it's yours. So then, yes, it works out very well for me.
Heidi Friedman: I'll take it then.
Paula Edgar: Tell everybody how they can find out more about you, about your wonderful book, about the work that you do, and just how you would like them to connect.
Heidi Friedman: Sure. The book is on sale at 133 different places, but the easiest place is either BarnesandNoble.com or Amazon.com. It's called Love Lessons: 104 Dates and the Stories That Led Me to True Love.
I would love you to follow me on Instagram @lovelessons104. I also have a Facebook page with the exact same title as the book. On LinkedIn, you can just find me at Heidi Friedman or on Thompson Hine’s website.
I'd love to hear from all of you. I actually created an email—lovelessons104@gmail.com. Happy to answer any questions. I love to hear your love stories if you're willing to share them, or your questions as well.
Paula Edgar: Oh, I love that. I just thought about an idea. Listen, everybody, tell that person who needs to love better, needs to get love, love somebody else—whatever the thing is, they need to read this book and spread the love.
We need more love, everybody. Tell a friend, because we do need to spread more love. Heidi, thank you for joining me in the Branding Room. You're welcome to come back anytime you'd like to talk about whatever you want.
Heidi Friedman: I'm so honored. It was so much fun.
Paula Edgar: All right, everybody. Talk soon. Bye.
Heidi Friedman: Take care. Thanks.
