In this new episode to kick off 2024, longtime dating coach Damona Hoffman offers practical and optimistic insights from her book, “F the Fairy Tale: Rewrite the Dating Myths and Live Your Own Love Story.” Plus, listeners share their true stories about the search for love.

Damona Hoffman shares her definition of the “three-date” rule with DWG host Laura.


Damona hosts the podcast Dates & Mates and is also the official love expert for The Drew Barrymore Show.



This is “Dating While Gray: The Grown-Up’s Guide to Love, Sex, and Relationships. I’m Laura Stassi. And I confess, I’ve gotten really lazy about seeking out romance. I guess I’m not so secretly hoping someone will just magically appear in my life.

A myth that a lot of us carry is that we’re born just knowing how to attract people. This should just be easy. We can meet someone anywhere we go. And what we fail to acknowledge in that line of thinking is that that human interaction for dating specifically is learned. It is learned and the more we practice it, the better we get at it.

That’s Damona Hoffman. She’s a longtime dating coach, and she has a new book out. It details her practical and optimistic approach to helping people who want to couple up. Damona is sharing her insights. Plus, we’ll hear listener stories about the search for love. That’s all on this episode, “Dating in Real Life.”

When it comes to finding a romantic partner, I’ve sometimes turned to the woo-woo. Like that time when I asked a natal chart reader on this podcast to figure out if love is in the stars for me and my Coronavirus lockdown crush: actor Colin Firth. Guess what? Turns out I’m as astrologically compatible with Colin as I am with my ex-husband, 83%.

 JOE 01:48
Anytime you get anything over 70%,  feel fortunate. And if you get in the 80s, then you have a chance to even reach the 90s. But if you start in the 90th percentile, then you’re really one of the fortunate ones that the universe and the stars in the charts. It smiled at mine.

Just the other day, I got tempted when a former coworker told me about soulmate For 29.95, all I have to do is reveal some personal information over the internet. And presto, I get a detailed description of my soulmate, along with a drawing of his actual face, I guess so I can pick them out in a crowd.

Speaking of soulmates, have you heard about twin flames? Now if I understand that theory correctly, each one of us has only half of a soul. The other half is living inside someone else out there in this big old world. All we have to do once we find them is convince them of this inevitability even if they’re already partnered, even if it requires stalking that leads to a restraining order. That’s what happened to the woman who was convinced her twin flame is actor Ryan Gosling.


I definitely do not believe that there is one needle in a haystack, one perfect person that is predestined for you that is somewhere on this planet. Searching to be reunited with their twin flame like that to twin flame feels like storytelling, right?

I am Damona Hoffman. I am a certified dating coach. I’ve been coaching people on how to find love online and offline for 17 years. And my new book is called “F the Fairytale: Rewrite the Dating Myths and Live Your Own Love Story.”

Okay, what a great title.


LAURA STASSI And I think it’s interesting that your book came out at a time when the Golden Bachelor has gotten so much press. And what I have found surprising is that it seems to me that people are more inclined to believe in fairy tale romance when older people are involved instead of realizing from my perspective that forming new romantic relationships is probably more complicated at this stage of life. Do you have any thoughts on that?

Well, I have a lot of thoughts on The Bachelor and rom coms and fairy tales and how they really set our expectations up all wrong for relationships. And I know why we want to believe it. And I I’m thrilled also that that — and I come from mainstream media. That’s my original background was as a casting director, and that’s what got me into reading dating profiles, because I would teach actors about having headshots that would stand out and a headshot is to a dating profile photo what a first date is to an audition. So I have lived in the world of media for a very long time. And we have been saying people want to see themselves reflected on TV and I have had many clients that are dating over 50 Over 60 Over 70 that are like, where are the dating shows for me. So I like the golden part of The Bachelor. I’ll leave everything else though.

So your book is for singles of all ages. But for this conversation, of course, we’re going to be focused on older singles. And we last spoke, I think it was in was it in 2021 or two a while back to I can’t remember when, however, not much has changed in my personal life. And I think I represent a lot of older people when I say I’m not currently dating, mainly because I’m fine on my own. But also because the process seems really daunting. Going online seems like a lot of time and energy with sporadic results. I just like to live my life and meet someone organically. So is there anything wrong with this mindset? Knowing the answer, because I read your book,

I was gonna say I love it, I feel like you’re leaving the witness here is wrong. I don’t want to tell anybody that what they think and feel about dating right now is wrong. However, I do want to inspire people. And I want to acknowledge what you are feeling the amount of time and effort and work like in use the W word work that does go into the dating process today. That is real, that is real, and it’s creating a lot of dating fatigue. However, I do see a lot more opportunity. And particularly I do see more opportunity for older singles, then really ever before in history. And I feel like your dating app has to be a part of your dating portfolio. Because it takes actually a lot more work to meet someone out in the wild IRL. But just the availability of just having access to so many people in so many different worlds to like your dating pool is expanded from your backyard, your community to anywhere in the world. Yeah, I think that’s a really great thing. But that said, there are some pitfalls and challenges for singles over 50. Yeah.

So I don’t know what I don’t want to have so much I want to talk to you about. Let’s talk about the myths. First you discuss some myths in your book. Yes,

I identified the four biggest dating myths. But believe me, Laura, I wanted to have, I wanted to have 20 minutes. And my editor was like, Can you narrow it down? Okay. The way I work with clients, I kind of see dating as a continuum. And it’s, it’s a process that you kind of wash, rinse, and repeat until you get to the result that you’re looking for. And I identified the myth that governs each phase of the dating process. So you mentioned the list, Smith, that really comes up in that free dating phase. In the mindset phase, I’m thinking about dating, I’d like to have someone in my life. I’m considering going on dating apps, I want to meet someone in the real world. How do I even do this?

And that’s where, when I, when clients come to me and I say, Okay, well, let’s figure out how to do this, what are you looking for? They either will tell me, I’ll know it when I see it. And if you haven’t seen it yet, maybe you don’t know it. Or they will have a list a mile long, that is completely unrealistic. Or they’ll hand me the same list that my 10 prior clients handed me thinking that it is a unique list thinking that they’d really spent time developing the list for themselves. And what I can see from my vantage point is that their list is really being dictated by our societal beliefs by our families of origin by so many things that we consume by the rom coms and the fairytales. And what I want people to do when they’re in that mindset phase of dating, is to get underneath all of the things on the list, and really drill down to the why, what is what is behind each of those choices and figure out is that really, ultimately what you want, or is that what you think you can get, what society has told you should have, or what somebody else wants, that doesn’t even actually equate to your relationship goals.

I think some older people might say, you know, I’ve had a relationship before I’m happily living by myself. And so I want to create this list because I know exactly what I want. I have all these Two years of experience behind me,

I’m not going to knock anyone that has really taken the time to think about what goes on this list. But in my experience, a lot of times people haven’t thought about that list, or that’s the same list that they had 20 years ago. And maybe it doesn’t apply to dating today, it’s helpful to really identify the three must haves, the three most important must haves, and the one deal breaker and what is actually a deal breaker. You know, we’re always looking for red flags and deal breakers. What happens if we reframe that and we start looking for more green flags?

Okay, the rules myth, what is that?


That’s where the bachelor comes in. That’s seeing the dating as a game to be won or played, you know, looking for the shortcuts if I do X Hill, do ye? It’s not a game dating is not a game. It’s a dance. It’s a dance surely. But it’s not a game. And there are no shortcuts, believe me if my book could be all shortcuts, and I could just hand it to every single person and they’re like, Oh, perfect. And they meet their person tomorrow. That would be amazing. But when we’re talking about human interaction and human behavior, I really believe in slow love. And you have to walk through all the steps. Slow love, can you define that? Slow love really means taking the time to see who a person is, and see how well you are aligned on the four pillars.

So the we talked about the myths, but I identify that there’s sort of an antidote to all of the myths that we’ve come to believe. And through my work with clients and the successful couples that I have seen emerge into the world, I found that there were four pillars of long term compatibility that were present every time. And the antidote to the list myth is having shared goals for the future. And that’s why sometimes people don’t take the time to figure that out. And then you end up six months, 12 months, two years down the line, and you’re like, Oh, we’re traveling completely different paths here. So we need to frontload the goals and really hear people when they let us know where they’re at. And then the other part is the values. That’s really the antidote to the rules myth of not playing the game, but really seeing who’s in alignment with you in the way they look at the world and the way they live their life.

HOLLY 12:49
Hello, my name is Holly. I really love your show. I think it is very entertaining, as well as being full of great insights. I’m 67 years old. I was married for 45 years and separated only about eight months ago, I would be divorced, but our financial advisor advisors strongly against it, as long as we can tolerate the situation. And so far that is working out because we live in separate states. And we are switching off between our permanent home and our vacation home. I went online, dating online within six months and found someone right away. I was at a state at the time. And so we didn’t meet for almost six weeks. But we talked on the phone for hours every single day and really, really hit it off. And I was thrilled.

When we finally met, I was very attracted to him physically. And he made me feel very sexy and pretty. And I’ll admit we hopped into bed on the first date. I hadn’t had sex in over 20 years and I admit I really needed it. He was a very attentive lover. But during pillow talk, he started talking politics. It turns out he voted for Trump and his very right wing and I am very liberal. So that was my first red flag. And then it seems that is kind of a bully and simply could not retain anything. I told him about my life about my volunteer work about my grandkids and he couldn’t remember their names much less even whether they were boys or girls even though I had told him showed him very many pictures of my grandkids. So I went back online dating, I put up a very detailed profile with good clear pictures, some of them with me doing my favorite hobbies full length poses, filling out all the personality questions in the hobby questions.

And out of the last 40 men who have messaged me with more than just a smile, only one of 40 has been real. The con games being perpetrated by these men are quite elaborate. One person sent me a phony Facebook profile, and a link to his employment website, which had him pictured as the CEO. That wasn’t real. And several others have said that they’re from the Netherlands, Wytheville Netherlands, I don’t know. But they say don’t be surprised if they have an accent when we speak. I have spoken to two of them on the phone, I use a phony phone number, and it rolls over to my real number. So no one knows my real phone number. And when we speak, they can’t pronounce the name of the city that they say they live in. And it just goes on and on 39 in a row.

And I just wondered, Is this happened to everyone? Is this common? Um, it’s very discouraging, very disheartening. I am pretty much giving up at this point. I have been told I’m a reasonably attractive person. So I don’t know why I am not attracting anyone real on these dating websites.

Instant chemistry, online dating, we’re exploring that and more with Damona Hoffman. That’s after the break.


LAURA STASSI 17:06One of the myths that you say is a chemistry myth. And I have a problem with this. Helen Fisher, I’ve interviewed her for the podcast and you have information from her in your book. And she talks about how generally speaking, heterosexual women can let attraction grow, they don’t need that instant chemistry, to be able to get to know someone. But men, heterosexual men need some sort of physical attraction in order to grow a relationship. So I think when you’re talking about a chemistry myth, let’s address our conversation to heterosexual men.

I just want to clarify, Laura, that when I’m saying chemistry is a myth, it’s not that I don’t believe you should have physical attraction, there has to be some level of physical attraction. I just don’t feel like when you when you feel those butterflies, when you’re weak in the knees, and I work with men and women I work with I work with LGBTQ singles. And I can say that, yes, what you said is exactly right. If a man does not find his match attractive physically, he will not be investing in the relationship growing right? However, it’s kind of based on the idea that you’re not even going to be on that date if there isn’t some level of physical attraction. So the chemistry myth is what governs the actual date when you actually meet. And I see too many times that people are looking for this spark, they’re looking for this, quote, magic to happen the first time they meet someone, and a lot of folks after the first date, are throwing in the towel saying, Well, I didn’t feel anything. So you know, just forget it. But so many times on those first dates, we have nerves, we have expectations, there’s a lot that’s competing for our emotional, and, you know, mental, physical bandwidth. And a credit to Dr. Helen Fisher, because she really coined the term slow love and slow dating. Can you see what happens if you let curiosity drive those first few dates as opposed to chemistry? I’m curious about this person. I want to know more about this person, I want to spend more time with this person, and then let that chemistry develop. By the third date, I say if it’s if you don’t if you’re not, what would it be like to kiss this person or you know, you’re not having those thoughts by the third date, then it’s probably not a future relationship. But could we just space out that interaction a little bit more and give the true deeper chemistry time to develop?

Okay, so you mentioned three dates, your three date rule is different from what I’ve heard a lot of people quote me as a three day rule. So explain your definition of the three date rule.

I just say, in those first three dates, all you need to know is that you’re curious enough about that person to spend one more hour with them. Don’t start thinking about well, how, how is this going to play out in the future? Well, they have grown children, and I don’t really want to have any children in my life, or, well, they live in this location, and I’m over, we get so far ahead of ourselves. And we need to just stay in the moment those first three dates, if by the third date, you’re not feeling some romantic Spark, then maybe that’s your friend. Or maybe that’s somebody else’s match. Okay, but give it that time. But I want to hear I want to hear you’re three-date rule.

Oh, well, I only somebody schooled me this during Season 1 because I always thought too by the third date, if you haven’t felt that spark move on. But he’s like, no, if you’re not sleeping together by the third date, move on. What he told me was that he had read this in some men’s magazine. So apparently, that is what’s being put out there. Excuse the pun, put out.

I love the pun actually. Yeah, I mean, of course, you’re this is this an app, the fairy tale and my guidelines are developed over the 17 years that I’ve been coaching singles. This is what I’ve consistently seen, be sort of a decision point between is this moving forward? Or is this fizzling out? Sure, you’re going to hear different rules, different guidelines from any person that you speak to. And I’m not the kind of dating expert who’s going to say, though, you can’t sleep with each other until X date or if you haven’t slept with each other by this day, it I really, actually kind of separate the physical relationship from the emotional relationship development.

And you know, if there’s, there’s any criticism about the book, I don’t really talk about the sexual relationship. There’s a lot of great sex experts out there that, that do that. But I’m really interested in the emotional development of long-term relationships, whatever your relationship goal is, I do find for a lot of older singles, it’s different than for, you know, a 30 Something woman is going to come to me with plans for marriage, kids, have, you know, the picket fence, the whole thing? Yeah. And sometimes older single say, Well, I don’t even want to live with somebody, I don’t want to get married again. I just want companionship. And that’s fine, too. All answers are correct.


Hi, Laura. I’ve really enjoyed your podcasts these past few seasons. And we have learned a lot by listening and just wanted to share my story a little bit. I’m in my mid-50s and been divorced for about five years now. And I had kids later in life, and I have post-divorce, I have part time custody of a middle school daughter and another daughter in her last year of high school, and then a 20 Something son, who I guess is kind of on his own, but starting into military training. As far as my dating experience, I dated a lovely lady who is in her later 40s. And her kids, of course, were out of the house as most that age range are. So she didn’t have any kids. And even though we really seemed to click surely did not want to be known end up being known as the quote unquote, evil stepmother, or stepmother at all. And understandably, she wanted to a partner who had greater gating, travel flexibility than I could give to seems like the type of person you know, who I’d be interested in would be close to my age, has already been there done that with children is not interested in raising any more kids. And so for now, I decided to sit on the dating sidelines and just focus on race and my own.

There’s a lot of reliance on dating apps right now. And I’m a big fan of dating apps. That’s how I met my husband, Tao the majority of my clients I’ve met. Yeah.

You mentioned that you’re a fan of online dating. And I did want to talk about that. Because as I said earlier, a lot of us have tried it and have had very mixed results. And it just is, you know, I just got an email the other day from a woman who said, you know, I hear about all these people on your show, and, you know, they’re meeting people and it’s not working out because I can’t even get any action online at all. Nobody’s even responding to her. What would you say to someone like this who wants to date but just as not finding the apps who are working for them?

Well, the dating apps are tools, they are a piece of technology. And they need to be run managed us in a certain way. So I say it like this, if I’m not big into construction, but let’s say I was trying to hang a picture on my wall, and I’m using a saw. And I’m, I’m hammering into the wall with my saw. And I’m like, You know what, this is really frustrating, Laura, I cannot get this nail to go in. And you know what sauce don’t even work. Oh, oh, if I had used a hammer, that would have gone a lot easier. So we just need to learn, learn to use the tool, the correct way, the most effective way for ourselves. And the reason I do this work that I host the dates and dates podcast that I wrote this book is because I know that that information, there’s information out there, but a lot of people don’t know what to do, don’t know who to listen to, or how to design their dating profile, or how to impact the algorithm with the, the, the way that they use the app, in general dating is a set of learned skills. So we have to be willing to build to build those skills. And of course, I have tips on how to strategically impact the algorithm or design the dating profile. Like it sounds like the person that you just mentioned, has a profile problem. And, and that’s honestly, like the easiest thing to fix. It’s just new photos, a catchy bio. And then we can talk about the strategy and the activity to get that person more messages.

Okay, let’s say we’ve really taken a lot of time and effort, we’ve got what we think are really killer photos, we’ve got a great write up. Should we be devoting a certain amount of time per night per week? What would you suggest? I

think that’s a good idea. So the other thing that has changed, so dramatically, since I began doing this work is the speed of dating, you’ve probably experienced this too. And really, it’s not just the speed of dating, it’s the speed of all of our communication, like the average text receives a response within 90 seconds, which blows my mind. I mean, this is all of all texts, like this is text from your, your daughter, this is text from your best friend is text from your boss. So sure, 90 seconds is short. But what it’s doing is it’s impacting people’s expectations around communication. Yeah. And so if you have a dating app, that you’re kind of set it and forget it, and you haven’t checked in a week or two, it’s going to be a lot harder to revive dead threads of conversation, then if you were responding immediately, like I used to, when the sites were more a thing than apps, they a lot of them used to have the online now feature. And that was one of my like, secret weapons that you even back in the early days of online dating, because if someone was a captive audience and online at that moment, in the mindset of I’m looking to meet someone right now, in this moment, the chances of that connection moving forward, we’re much greater than if a message sat there for more than a week. And the longer it goes, the less chance that that that’s going to materialize into a real meet up.

Yeah, I as you’re talking, I’m thinking about everything I’ve been doing wrong. Because it to me, it’s like, I don’t want anybody to know that I’m online on a Saturday night at 9:30pm. Do you know what I mean? It’s like, I don’t know, is there any? And maybe part of this is sort of the lingering, traditional way I was brought up where you know, women you want to play hard to get you don’t want them to know that you’ve got zero options.

Well, I just want to acknowledge first of all, you even saying that allowed, it takes a lot of courage. So yeah, no, it does. It does. And I’m sure a lot of your listeners relate to that. And that’s the rules myth. We have been told a lot of rules that maybe were true at one point, but are not necessarily true, because we’ve changed so many of the other factors. Like you don’t get to change one element of you know, one of the numbers that you plug into the equation and have the result end up being the same. We’ve changed so much from it. Technology to gender equality, to adjust the availability of different of options outside of our local community. And like I was saying, the expansion of our dating pool to anyone in the world, there’s been so many changes even around age and dating. I mean, you look at the belief system, a generation ago. And we, as a society, we don’t even support older people, even dating, like your relationship ended. And that may just be it for you. And so what we do is we fill our lives with things that give us joy. And I talked about this in the book, how I was so married to my job, and the harder I loved my job, the more I got back from it. So you put more in, and then you get more in return in that area, and the other areas atrophy. And so that’s, I would say, for older singles that that, take my courses and do my programs and coaching. That is one of the bigger challenges when you have been living your life and practicing your life in a certain way. If you’ve been single for a long time, and you’ve built your life the way you like it, yeah, and I totally get that. But if you also want a relationship, there has to be enough space for some one new to come in. And for some of those routines, to change.

DIDI 31:29
Hi, lar, this is getting in the San Francisco Bay area. I am in my early 50s. And I started going gray when I was 20. And I’ve always colored my hair, it just makes me look and feel younger. And I definitely think it helps me to stay ahead of the game in my career, and definitely gives me an edge in the dating world. No doubt about it. So yeah, I listen to dating while Gray, but I will not be gray anytime soon. That’s it bye.

LAURA STASSI For anyone who is hesitant to jump into the dating pool, or who have they’ve jumped in, and it’s like, God, let me get me out of here. How do we actually go? How do we start? How do we keep going?

It’s a common response or like I jumped, it’s to call me out. You don’t have to jump in, you can just put your toe in first. Whatever is comfortable to you. But you’ve really got to start with clarity. That’s why I began the book with the mindset phase. Because we can waste a lot of time and emotional energy. When we’re like, what am I even doing here? I don’t know about dating apps. This feels weird. This is new, this is different. And if you haven’t made the decision that you’re going to try this for a certain period of time, like people I would always ask people before, have you tried online dating? And I would hear oh, yeah, I did it for you know, for two weeks? Well, two weeks isn’t enough time, you know, to really see the results. The algorithm is just barely getting to know you and then you’re already off. Yep. So commit to trying something new for doing something differently for a set period of time and then reevaluate, track, review, adjust, implement leap, then you can, you can really see where what needs to shift in your dating experience. Or if you want to take a pause on dating altogether. I do also say that it’s not always your season, to find love, just whatever you’re choosing, choose it fully. Choose it mindfully and be right where you’re at that moment.

I like that — choose it fully choose it mindfully. I mean, I’m the person you just talked about, I signed up for a three-month membership and it’s like a week later — I can’t deal with this next time. So thank you for this.

Day by day, Laura. Day by day.

Day by day … shout out to Godspell. That’s Damona Hoffman, dating coach and author of “F the Fairytale: Rewrite the Dating Myths and Live Your Own Love Story.” Thanks, Damona. I guess I need to stop dreaming about shortcuts. Thanks also to the listeners who shared their experiences. That’s it for this episode. But there is so much more to dig into about making and keeping romantic connections on your own terms. And what’s with all the scammers anyway? So stick with us. We’ll explore much more as 2024 unfolds.


Dating While Gray’s audio production and mix is by Steve Lack: Audio. Theme music by D. Peterschmidt. Please like and follow Dating While Gray wherever you get podcasts. That way, you’ll never miss an episode. And, if you’re so inclined, leave a review letting everyone know what you love about us.

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I’m Laura Stassi. Thanks so much for listening.

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