Does an Age Gap Mean My Relationship Is Doomed?


Hey Doc!

Hope you find the time to read this heart-breaking story.

I (M, 30) met this woman (F, 38) almost 3 years ago at a bar. She was a little drunk and recently divorced, like, days ago. 

We went home and made love that same night, and talked until very late hours. The chemistry was – and still is- really strong. 

I thought she was younger (she certainly looked so!), she revealed her age, shortly before leaving. I didn’t know what would happen later so I didn’t care.

The first months the relationship developed really slow and easy, and I was always clear about how I wasn’t interested in “formal” relationships, like “girlfriend”, marriage, and so on. Still, I was all-in for real love, respect and sincerity. She was OK with that, most of the time, but after a year or so she demanded more commitment or spending more time together. I was OK with that too then, and I could have kept it that way, like, forever.

But as time passed and love grew, she “realized” (thanks to me , and the relationship, she says) that she did want marriage, family, etc. I was like, yes, me too, just not now.

Flash-forward to few weeks ago: she just went on a 4-months trip to a far away country, and last time we saw she said when she comes back she doesn’t want to live alone and she doesn’t have much time if she wants to be a mother. She will not push me in any way, but it would be very hard for her to continue seeing me as I’m not “in the same page”. 

So basically it was like a break-up.

I know for sure that in all this time she never saw anyone else but me, she loves me – and I love her. We are really good friends and I’m really attracted to her.

I have a good job but still feel like I need to work on some personal issues and get to have some more life experience before fully committing to a family.

I have so many fears, and the age gap is a big issue on my mind, as I would hate that in, let’s say, 10 years, I’m no longer attracted to her and pursue younger girls. I was a “late bloomer” and haven’t met “many” women, and sometimes I feel like I’m “missing out” on something.

Please Doc, share some words for me about this. Be brutally honest. I need perspective

All the best and many thanks in advance

My December Romance

Well, not gonna lie MDR, this is probably the first age gap question involving a (slightly) older woman, instead of an older man interesed in pursuing younger women so hey, congratulations on this.

But – as is so often the case – you’re asking the wrong questions. Especially since this isn’t really an age-gap problem, it’s an experience problem. Specifically: you don’t have any, and it’s kinda freaking you out.

So let’s get something out oft he way, right off the bat, ok? Being a late bloomer isn’t really an issue except in your own head. Whenever I talk to older (male) virgins or late bloomers, one of the things that comes up fairly consistency is the fear of “missing out”. Whole lotta folks worry that they’re missing the opportunity to sow their wild oats, have their “slut period” or whatever they want to call it.

But hey you want me to be brutally honest? OK, well here it is: most of the time what they’re actually saying is that they want to bang the chicks they were into as teenagers and twenty-somethings. They can’t quite bring themselves to straight up say “Yes, I want to have lots of casual sex with women when they’re young and perky and apparently immune to gravity”, and instead talk about “missing out”. It’s always framed as though there was a limited window of time in which you could have lots of crazy, no-strings sex with young women and as soon as you age out of that window (which can be anywhere from 35 to as young as 17, depending on who’s angsting about it) then you’re just shit out of luck. Supposedly all women past the age of &ARBITRARY_YEAR are either coupled up or looking for marriage and children, not wild sexual adventures.

Here’s the truth: this is pretty much sexist bullshit. While yes, while it becomes more challenging for women to have children as they get older, the idea that there’s a window for sexual adventure or sleeping around or whatever is false. The folks who are the most invested in this idea – which often runs parallel with “women ‘hit the wall’ at 27” red pill/MRA bullshit – tend to either have next to no relationship experience or actively dislike women. In both cases, this belief is based more on vibes and retrograde ideas about women and female sexuality.

Is it true that the older you get, the more likely you are to find women who want to get married or have kids? Yeah, especially since people are waiting longer to get married and to start families. Does that mean all women are going to be actively looking for marriage or dudes with father potential? Fuck no. In fact, one of the things you will learn is that as women get older, they tend to be more comfortable in themselves, more confident in their sexuality and – importantly – more willing to pursue what they actually want instead of what they’re “supposed” to want. Sometimes that means yes, they want to settle down and have kids. Others though? Others fully embrace that no, they want radically different things… including fucking around the way they didn’t (or felt like they couldn’t) in their 20s. When they were younger, they had other priorities, they had other commitments and they often were more worried about what they were “supposed” to do. But as they get older and more confident, they start to run out of fucks regarding what society tells them.

And let me tell you, a sexually confident woman with no fucks to give is a glorious and terrible thing.

But what about you? You’re 30, and you’re worried that you’re going to be “missing out” if you decide to commit to your maybe-ex/maybe-not girlfriend. Well… yes. Here is another truth: you’re going to be missing out. That’s what commitment means; you’re committing to building a life with that person and (presumably) only having sex with them. And even with ethical forms of non-monogamy, you’re still going to be missing out. Yeah, it means you aren’t restricted to sleeping with only one person for the duration of your relationship, but it does mean that a lot of folks are going to opt out in advance.

But this is going to be true no matter who you date or when. Making a choice to be in a relationship with someone is ultimately making a choice that says you’re going to miss out on relationships with others. You will always be making compromises when you settle down with someone, because there’s no settling down without settling for. Nobody – not any celebrity you care to name – gets everything they want in a relationship. What you do, if you’re doing things right, is choose a relationship with someone where what you do get is so damn good that you’re ok with what you’re having to give up in exchange. Yes, you may not be able to go out and hook up with the young nubile women you see on the Internet or at the club or whatever, but you get so much awesome stuff with your partner that the rest is an acceptable price to pay. Especially since you won’t get what you get from your partner from anyone else.

Well, ok, so does that mean that the answer is to slut it up now and get it out of your system so at least you can say you got to experience X, Y and Z before you settled down?

No. No it doesn’t. Because here is another truth: the idea that you get “fucking around” out of your system and then settle down isn’t real. There’s no “getting it out of your system”. You’re a mammal with a sex drive, and an ape besides; you’re always going to be attracted to other people, always going to want to sleep with other people, regardless of age or relationship. And so will the people you’re dating or commit to. That doesn’t go away; it may go dormant in the early days of the relationship, when the New Relationship Energy is running hot, but it’s built into the human experience. Monogamy just means that you promise not to have sex with someone else; it doesn’t say a damn thing about not wanting to.

And here is a third truth: everyone you date is going to age. Everyone you date is going to grow older. Time makes fools of us all and gravity and entropy always win. You can try to avoid dealing with this by, say, pulling a DiCaprio and breaking up with women once they hit a certain age, but honestly? Even DiCaprio can’t pull that off, certainly not forever. So if you decide to settle down and commit to only one person, then you’re going to see them get older. Their skin is going to sag, their breasts are going to droop, their butt won’t be as perky as it used to be. But will you notice? Will you even care?

That depends on a lot of things. To start with: growing old with someone is a slow process and these are changes that occur over time. Over time, they’re things that happen, but as they happen, they just get incorporated into our idea of who they are. Its like looking back at a picture of you and being shocked at how young you are; you don’t think about it until you see that side-by-side contrast. But also, when you love someone, you still see the person you fell in love with at the start, no matter what’s happening with their skin or hair, because love may be physical, but it’s emotional and mental too.

Now here’s a final truth: you don’t know if your relationship with your ex – should you choose to try to pursue things with her – will be your last. Nobody does. Every relationship comes to an end, except the one that doesn’t, and you have no idea which it will be, or how it will end. Sometimes it ends because the relationship has run its course. Sometimes it ends because somebody messed up, or because you weren’t compatible in the ways you needed to be for the long haul. Or it may end because a double decker bus crashed into the both of you; you have no idea. You just want to be sure that, if you’re committing to somebody, that they’re worth it.

I will say this: if you’re not sure you’re ready for marriage and a family, then you should let this relationship go. While I’m sure she’s wonderful, there’re few things more corrosive to a relationship than someone making a commitment that they don’t actually want. It’s one thing to question whether you’re ready to have kids or in a place emotionally or financially to support them. Its another to start a family just because someone else wanted to. She’s laid her marker down; she wants marriage and kids on a very short timeline. You aren’t sure. If that’s the case, then you’re better off letting this relationship end. It’s better for you, and it’s kinder for her. You’re not giving up on things or “missing out”, you’re both letting each other go, so that you aren’t holding each other back from meeting the people who are right for you.

If you know you want to screw around for now – and trust me, no judgement there, I’m all in favor of folks being sluts when they want to – then be honest with yourself. If you are worried more about not having ‘enough’ before you decide to settle down? Well, you may want to think about what enough means, and why you want it. Because sometimes what you think you want is what you’ve been told you’re supposed to want. Know yourself, know exactly what you want and why before you decide.

And whichever way you do decide? Make sure that it’s worth the price of entry.

Good luck.


Hey Doc ! 

Thank you for your articles they’re really helpful.

I’m a 29y male (30 in a few months) and I’ve never had any kind of relationship ever. I’ve read a lot on your website and that helped a great deal.

Living in a city in Europe with 5+ roommates, having childhood friends from 20 years ago still around, I think I’m in a good place. I’m tight with my family and I’m doing therapy once a month.

My question :

How do you put aside those almost 30 years of nothingness love-wise and keep the drive to be cheerful and hopeful around people and myself? To even kiss a woman seems so, so far away and plain impossible. I try to always remind myself that being single is just data as you say but damn is it hard.

I know there’s a big anxiety and self-esteem issue here and I’m working on it in therapy. On top of that I’m slowly recovering from a nasty case of Oneitis for the last two years…

Thank you,

Sad and Happy

Well, you’re already doing a lot of what I would otherwise tell you to do, SaH. You seem to have a pretty good head on your shoulders, you have a good grasp on what’s driving this and you seem pretty self-aware and emotionally intelligent. Those are all good things, and they’ll go a long way towards helping you.

Here’s my question: what are you doing for yourself? Not in terms of personal development (well, except that’s good too) or emotional and psychological health, but things that make you happy?

One of the things I’ve seen in men who focus like lasers on being virgins or not having had girlfriends or sexual experience (including kissing, non-penetrative sex, etc) is that they’re so focused on what they don’t have, they neglect or miss on what they do. All of their ideas about what happiness or fulfillment or satisfaction mean come down to “get a girlfriend and everything will fall into place”.

The thing is, though, is that most of the time, that’s the only thing they think will make them happy or give them hope. And when it becomes the only thing you’re focused on… well, that actually makes things harder.

Think of it like playing Elden Ring or Bloodborne or any other Souls-like games that are famed for their difficulty and their grind. The more you try and the more you fail, the more frustrated you get. The more frustrated you get, the more you get sloppy. You rush, you cut corners, because you want to get back to the place where you failed and try again. Problem is, at this point, you start to lose more ground because your rushing means that you’re making mistakes, and those mistakes mean you’re dying before you even get to that boss fight. That makes you even more frustrated because you know you can beat that part already, but now you’re failing, which means you’re trying to get past that section as quickly as possible and… well you see how it goes.

But if you just put the controller down, go do other things and come back later? That’s when you are able to just soar through everything, beat that boss fight and move on to the next chapter of the adventure. You were able to relax, unclench and focus on other things and come back when you’re rested and ready.

Right now, dating is that boss fight for you. So what are the things you’re doing in your life that make you happy and bring you joy that aren’t dating? What are the things in your life that you’re passionate about, that make you want to get up in the morning? What are the things that you do that make you feel like you’re connected to something bigger than yourself – a part of a community, not just an individual?

These aren’t idle questions. The key to dating and social success is having a great life, not hoping that dating will give you a great life. Spending time on things that you’re passionate about, doing things that make your soul sing and make you feel satisfied make you a more interesting person. They ease the pressure of “you need to find a relationship to be a REAL man” or the idea that ONLY a relationship will make you happy. They remind you that sometimes the love of your life is the love of your life; a partner to share it is the value-add, not the load-bearing support.

Yeah, “It’ll happen when you aren’t looking” is a cliche, but it’s a cliche for a reason. Focusing on living an awesome life takes the pressure off of yourself. You’re better able to bring incredible people into your life when you’re having a good life because you’re doing things that will draw them in almost without een trying. And as you bring those people in, you’re bringing in not just potential friends or partners, but a network. Those people may not be the folks you want to date… but they may be the people who will introduce you to the people you want to date.

The more you have in your life that makes you happy and makes you feel great about yourself, the easier it becomes to meet people. And, importantly, it becomes easier to meet the right people. So don’t hold onto hope, go seek it out. Go do the things that make your world a better place. Everything will flow from there.

Good luck.

This post was previously published on and is republished on Medium.


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