233. Lessons from 104 Dates with Heidi Friedman

Written By Sade Curry

In this heart-to-heart conversation, I sat down with Heidi Freeman, successful attorney and author of "Love Lessons: 104 Dates and the Stories That Led Me to True Love." Heidi shares how turning 40 sparked her quest to understand what true love looks like by interviewing couples in strong relationships. What began as research turned into 11 core themes about authentic connection. With refreshing honesty, Heidi opens up about her 104-date journey, complete with hilarious mishaps, surprising insights, and the beautiful moment when she finally met her husband Will.

This episode cuts through the anxiety about modern dating to remind us that love requires resilience - and is worth 100 disappointing dates.

Key Moments

  • Turning 40: Heidi realized she didn't know what true love looked like or felt like and decided to interview couples in solid partnerships

  • Research: Heidi interviewed 50+ couples separately to find themes

  • Mutual reciprocity: The most impactful insight was how partners take turns supporting each other through life's waves

  • The myth of love at first sight: No one Heidi interviewed mentioned this - instead they talked about initial connection and safety

  • D04 dates: Heidi shares both hilarious dating disasters and meaningful lessons learned

  • Finding Will: How she met her husband through yoga connections and recognized the difference in how she felt

  • Dating in the wild vs. apps: The benefits of meeting people through activities vs. online

Quotes

"I had to put on my big girl underwear and go back out there." - Heidi on persevering after dating disappointments

"I think it's not us. This is the way we are socialized...to value relationships, which is awesome. But then we're also socialized to put our own personal value in relationships, and that's what's harmful." - Sade Curry

"Mutual reciprocity and safety... even if you didn't have all the other sprinkles in a relationship, but you had these, you could make a good relationship out of that." - Sade Curry

"What if the next date is him? I would constantly say that to myself when I didn't want to go." - Heidi on staying hopeful

About Heidi:

Heidi Freeman (formerly Goldstein, born Eisman) is a successful attorney and partner at a large law firm specializing in environmental law and social and environmental governance-based counseling. She's written her first book, "Love Lessons," chronicling her dating journey and the relationship insights she gained. Heidi has previously written for Bloomberg Law, 360, and other professional publications. She lives in Cleveland Heights, Ohio with her husband Will and their blended family - two children of her own and two bonus children with Will.


Connect With Heidi

Ready to Transform Your Dating Life?

If this episode resonated with you, I'd love to help you apply these insights to your own dating journey. Book a complimentary dating consultation call with me at sadecurry.com/info and discover how you can build the confidence, clarity, and connection skills to find your perfect match.

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EPISODE TRANSCRIPT

SUMMARY KEYWORDS

dating closure, dating anxiety, relationship endings, self-reflection, coaching, emotional healing, dating journey, life-or-death situations, socialization, certainty, insecurities, healing work, dating after divorce, consult call, dating Collective

SPEAKERS

Sade Curry

Sade Curry [00:00]

Hello everyone. Welcome back to the podcast. This is Sade Curry, your host. This is going to be a super short podcast episode. I really just wanted to share something that happened with one of my clients around the need for closure when you're dating, and I've noticed that this can be something that holds women back when they're dating, and it doesn't work out.

There is this need that we talk about for closure from the other person—that last conversation, where we want to get an explanation for why things happened. We want to know, what does you know? Like, why would you say this and then do this? Why are you showing up this way in the dating world, like you were a liar? We want to tell people how we feel about what they did. We want to tell people why what they're doing is wrong. We want to understand, and this is perfectly normal.

Our brains are story making machines right. We have a desire for knowledge, and we have a desire for certainty and to understand what is happening. Because, you know, in caveman days, which is where our evolution stopped with our brains, if you weren't certain about which berries to eat, there was a very fine line between life or death, right? If you weren't sure if that snake was the kind that you could play with or that was the one that was gonna kill you, it was a very fine line between life and death, and so humans had to work on creating a lot of certainty for themselves to make decisions.

Except that we live in 2025 and there's so much room for gray, there's so much room for nuance. At least in the dating world, especially with a relationship that hasn't worked out, and the person is moving on, or you're moving on, there certainly is not a life and death need for closure. There is not a life and death need to understand what happened or why the person did what they did. But our brains still put that desire in us. Our brains still respond in that way.

And one of the reasons that comes up now is that, well, if I don't know what happened, if I don't understand what happened, how am I going to prevent it? And that sounds nice. That sounds like, oh yes, if I can figure it out now, then I can prevent it in the future. I don't have to worry about it in the future. But that assumes that if it did happen again in the future, that that would be a life and death thing.

And so there's that sneaky way that our brain keeps us in this dating anxiety mode by making things that are not very important, important like that, that line right there, if you know how many times I have had to coach my clients on not making things that are not important in dating important, most things that are happening when you date are not important. So why does it feel like so high stakes? Why do they feel so important? Because we've been socialized as women to believe that our relationship status is a life or death situation, and that anything that could impact whether or not you are able to have a partner in the future is a life or death situation.

Now listen, there are very few things in our world today that are life and death situations. In fact, half the time we ignore the truly life and death situations. Did you know that driving to work is one of the most dangerous things you can do on any given day? Even more dangerous than that is taking a walk. I learned that recently, I'm like, what is happening like pedestrians get hit all the time. Now, of course it varies by city versus suburbs, but like, apparently this is a thing, cyclists, motorcyclists, pedestrians, driving, like, those are like, some of the most dangerous things we can do right now, eating fast food, eating sugar, like all of these things are things that almost guarantee that we're gonna have problems in the future.

But because we're not socialized, it hasn't been ingrained in us since we were babies, that these things were life and death situations. Our brain is like, "Yeah, this is fine. Another burger. It's okay, not a big deal." This is letting you know that just because you are feeling something doesn't mean it's true. Now, there are times when you're feeling something and it's true, but you need to know the difference. You need to know the difference between a true life and death situation and a dating situation that doesn't mean much, and this requires that slowing down, raising awareness, self reflecting, which is a skill. It is a skill that has to be practiced over and over and over again before it truly takes root.

This is what we do in coaching. This is a lot of my job as a coach is helping my clients stay on track with what they already know, helping them put it into practice, helping them practice it every day, helping them stop getting derailed every couple of weeks and starting from scratch over and over and over again and never creating momentum in their dating journey.

So now that you understand that getting closure from a person is not a life and death situation, if you can create that space, you can ask yourself, What am I trying to do here? What am I trying to get? What am I trying to create? Why do I need this closure? There are some cases where might be helpful for you. It might be useful to have that conversation.

In many cases where closure isn't happening, I have just found, through experience and working with women, that chasing that closure or refusing to give yourself that closure tends to be a waste of time. Chasing the closure from someone who doesn't think that they did anything is usually a waste of time.

So I wanted to ask for those of you listening who are going through something like that, where you don't have closure. And this can also apply to family members who did something, co-workers who did something, friends, friendships that ended, romantic relationships that ended, if you are still holding on to the desire for closure, if you are still chasing closure. If you're still texting too many times, ask yourself, what do I need right now? What am I trying to achieve? What is the emotion I'm trying to create?

For some people, you're trying to create certainty. You want to know that you know what you're doing, so that you know you never have another breakup in the future. For some of you, it's triggered an old wound from family trauma or something that happened in the past, and you're trying to heal that wound with the closure from this person, which I'm sure you know isn't going to work right? For some of you, it just triggers a lack of safety or a lack of knowledge, or for some of you, it triggers insecurities about who you are, whether you're lovable, whether you are attractive, whether you would make a good partner, if you are a person who is seeking closure, unsuccessfully, seeking closure over and over, or you find the seeking of closure draws you into situations you don't need to be in, it's useful to say why, and find out why—different for everyone. Right?

Ask yourself, why you're seeking closure, what you're trying to do, and then ask again, is this the best way for me to achieve the goal, because the goal is not closure itself. Closure itself doesn't do anything for us. We're using Closure as a stepping stone to an emotion we want to feel, or a resolution of something in our past or in our souls. By using the closure itself as almost like "I'll give myself permission to be healed if I get this closure."

So ask yourself what that is, and ask yourself, Is this the best way for me to achieve that? And this is a lot of what some of the work that I do with my clients, is helping them ask good questions about what's happening with them when they're in dating anxiety, when they're in overwhelm, when they're in despair, when they are reacting when they're dating out of something that has nothing to do with dating.

It's such a healing work to be able to say, "Oh, I was trying to do this other thing, but I was using dating as a stepping stone for it," so that they can actually start to achieve the things they want to do with their lives. They can start to achieve the healing and the closure and the growth and the maturity that they're missing, instead of chasing it in a place where they're never gonna get it.

So if you're a person who sounds like "I think I might be doing this in some areas of my life," you might need to listen to this episode a couple of times. And I also want to invite you to take advantage of a free, complimentary consult call with me to see if working with me in the dating after divorce Collective is the right thing for you to do with your dating journey.

If you've been spinning your wheels stumbling over dating anxiety or needing closure, or multiple heartbreaks, or not attracting the right person, or not knowing if your profile is the right profile, or, you know, being in these three month relationships that go nowhere. If you are stumbling over things like this over and over and over again, then you definitely belong in the dating after divorce collective. I want to invite you to join us. Schedule a consult call with me, with the link in the show notes, and I'll walk you through all the details and what we have going on and who's in there and what we're doing and how this can help you. Okay, thank you for your time and attention, and I will see you next time.

Sade Curry
Next

230. The Decade after Divorce with Dr. Toyin Falusi Nwafor