I Want To Get Back on The Dating Scene, But I Don’t Know How!

Estimated reading time: 23 minutes

Dear Dr. NerdLove:

I’m an almost 39-year-old single straight white male. I was a late bloomer and never even kissed a girl until I was 22. Got my first “girlfriend” and lost the v-card at 24. After that, I spent the rest of my 20s and early 30s casually dating and sleeping around until I decided I was tired of that and not going to do it anymore until I found an actual girlfriend.

And then it just never happened. I’ve had five “exes” (I think 3 of them would say we were just friends with benefits), and dated several other women, but nothing serious or long-term. Anytime I start describing my former love life, people assume I’m a player, but it’s more like the opposite.

What I used to do was go to bars, clubs, and parties all the time, and I hated it because I was a nervous wreck who didn’t want to be there, and I’ve done online dating and the apps for the past 20 years, and I go to every singles and dating event, and I used to let friends set me up on blind dates (which all were terribly mismatched), and I just kind of hit on every woman I saw. And I got shot down almost every single time. For the most part, the women who I dated pursued me, and I went out with them whether I was attracted or interested or not just because I was willing to go out with anyone who would chase me, and that’s why those “relationships” ended poorly.

Truthfully, the only women I ever REALLY liked were my friends, and we always only ever stayed just friends because none of them ever liked or were attracted to me. I know because I asked them out, too. And I know, “the Friend Zone” isn’t a real thing because that’s just women who aren’t attracted, but it kind of hurts when women I like didn’t like me back, and women who were attracted to me, I wasn’t attracted to.

And it wasn’t just a looks thing, either. About half the women I used to date or sleep with were ridiculously hot. We just had absolutely nothing in common and couldn’t get along outside the bedroom. The others, there was no compatibility or chemistry on my end, and it was just them chasing me for reasons I can’t fathom until they gave up.

Since I stopped doing all of that, nothing. I’ve been single getting closer to 4 years, and celibate about almost 6 because I held off on sleeping with the last couple women I dated unless/until there was actual mutual interest or attraction, and there never was.

Flash forward to the present. I’ve got most of my stuff mostly together for probably the first time in my life. I just don’t meet or interact with women anymore at all. The only time I see women is if they’re jogging in the park or working out at the gym or out grocery shopping or working at their job. And I don’t approach those women because I assume they don’t want to be hit on by some strange man, and the only thing I know about them is that they’re physically attractive.

Any time I’m out doing things that like and enjoy and would do regardless of whether I’m trying to meet anyone, like hiking and mountain climbing, and going to the farmer’s market, and going to coffee shops and book stores, and reading in the park, and going to art galleries and museums – all things you hear single women say they like (especially on their dating profiles) – they aren’t there.

So I kind of assume all the single ladies are on the apps, and at the bars, and so on and so forth, where I’ve never had much luck with them anyway because none of those experiences were fun for me.

I’ve reached the point in my head where it’s like that meme with the forking paths: go back to the way I did things before – be miserable but at least have the illusion of opportunity, or keep doing what I am – be content with a life I enjoy, but never really be happy that I don’t have anyone to share it with.

Ready to Finally Meet Someone Special

I can tell you exactly what the problem is RFMSS: you’re giving yourself a false dichotomy here. You’re presenting your situation as though you have only two choices: keep doing the stuff that doesn’t work or give up entirely.

Brace yourself, I’m about to blow your mind: how about you choose the secret third thing and do things differently?

I mean, your struggle here isn’t a mystery. It’s all summarized in this line here: “What I used to do was go to bars, clubs, and parties all the time, and I hated it because I was a nervous wreck who didn’t want to be there”

Well gee, I can’t imagine why you weren’t meeting people you liked when you kept going to places you didn’t enjoy. It’s almost like the sorts of people who love going to those places aren’t the sorts of people you would actually be compatible with.

You follow this up with how you would hit on people indiscriminately and how you mostly dated people who asked you out whether you actually liked them or not and, again, this didn’t lead to a happy or successful relationship. I mean, I hate to belabor the obvious but have you considered that this is your problem?

You may have read about how many women have decided to opt out of dating all together, choosing to stay single rather than to choose a relationship with someone who doesn’t meet their needs, nor makes them happy. Well, now you know exactly why they made that choice.

Long-time readers have heard me talk about how one of the most common relationship mistakes guys make is when they’re trying to fill a hole marked “girlfriend” or “relationship” and attempt to shove literally anyone into it. You, RFMSS, have provided a shining example of why this is a bad idea: it leads to relationships that ultimately only serve to make everyone miserable. Your partners feel like you’re only with them because they’re a warm body who got shoved into the role and you aren’t happy because there’s nothing to the relationship outside of, well, someone else’s warm body in proximity of yours. There’s no shared interests, no commonalities of background or values or anything other than a sexual connection if you even have that.

In fact, it’s a little telling that the only people you were attracted to were your friends. How many of them were your friends before you became attracted to them and how many of them were people who you became friends with because you were attracted to them but they weren’t into you? I strongly suspect the latter outnumber the former.

But here’s the thing: those are the people you should be dating. Not your friends specifically but people like them. You know, people you’re actually interested in. That’s one of the first changes you need to be making if you want to actually, y’know, date someone you like. Preferably without trying to pull the Platonic Best Friend Back Door Gambit first.

Now, you took a break to get your shit together and that’s a good thing. I’m all in favor of folks pulling back from dating so that they can get some clarity, their head on straight and put their lives in order. But part of the reason to do this is so that you don’t immediately go back and start making the same choices and mistakes that lead you to this position in the first place.

One of the mistakes that you can’t seem to shake is this very binary thinking, where you have a fixed set of options and you have to explore them the exact same way every time. You’re also misunderstanding what it is that women are saying when they talk about enjoying hiking or going to the farmer’s market; they’re not saying that “this is where I want to meet people”, they’re saying “this is what I would like to do with someone I’m dating”.

(Also, seriously: hiking and climbing are bad places to try to pick up women, holy shit.)

One of the things that leaps out at me ­is that you’re choosing a lot of solo hobbies or activities. The second is that you’re doing them in ways and at times that aren’t conducive to actually meeting people.  The third is that it sounds to me like you’re expecting these situations to work like going to the club – where you’re trying to make something happen right then and there. Part of the reason why cold approaches, especially at bars and clubs are difficult is that you’re trying to convince someone to start a romantic or sexual relationship with someone they’ve known for maybe 20 minutes, maybe an hour at most. This is not how the vast majority of relationships start.

Here’s the thing: for all that pop culture goes on and on about love at first sight, the truth of the matter is that we very rarely start dating someone the first time we’ve met them. Someone may be attracted to somebody they’ve just met but that doesn’t mean that they’re ready, willing or even interested in dating them right off the bat. Even when you’ve met on a dating app, there’s a “getting to know you” period between matching, talking and a possible pre-date date before the actual date. Even that very first in-person meeting is more of an audition than a date – a “let’s see if you’re who you say you are and if there’s any chemistry there” meeting rather than the start of a romantic connection.

This is one of the reasons why I tell people to do things that they enjoy in ways that connect them with other people who also like doing those things and to become a regular at those events or meetups. You don’t, for example, want to join an amateur pickleball league and immediately start hitting on people. Nor do you want to go once, decide that there’re no women (that you’re interested in) and never go again. You want to go and become part of the community, get to know lots of people and become a known quantity.

Part of this is so that you put distance between yourself and the other people who are there trying to treat the event like a sex ATM, but also so that people get to know you and see you often.

That last part – seeing you regularly and often – is the secret sauce of dating. The propinquity effect – the tendency for people to form close relationships with the people they see often – is one of the most underrated and underappreciated aspects of attraction and relationships. It’s part of what’s known as the “mere-exposure” effect – the more you’re exposed to something (or someone), the more you tend to like it. This is why when you first hear that pop single on the radio or Spotify, you may not like it… but after hearing it over and over again, you find it’s grown on you. So it is with people; we tend to become friends with our classmates and co-workers because those are the people we see regularly and spend time with the most.

So, instead of treating the park or the coffee shop like a quieter and low-key version of the club, you should be looking for group events related to the things you enjoy. Running clubs, for example, are taking off as ways to meet people for precisely this reason; it’s bringing together a bunch of like-minded people on a regular basis, with the added benefit of triggering the misattribution of arousal.

Your goal should be going to these events because you enjoy them and to get to know folks over time. You don’t want to hit on people like you need to make a love connection that day; instead, focus on getting to know people, seeing what makes people tick and – critically – whether they’re someone who is right for you. This doesn’t mean that you have to keep them at arm’s length or treat them like you’re only interested in friendship until the day you ask them out. You can and should be a little flirty – a little light, fun and teasing, not asking them to come viz you to ze Cazbah – because this sets the tone: yeah, you’re a cool fun guy who’s worth getting to know, but you are at least a little interested in them too. Just enough to make it clear that you’re looking for more than platonic friendship, even if that’s cool too.  

That’s radically different than continuing to make the same choices that lead to unsatisfying relationships or giving up on dating entirely. That’s just you not learning from the mistakes you’ve made in the past.

If you want things to be different, you have to do things differently. That means not falling back into false binaries, and it means considering that if the approach you’re taking isn’t working, then you should try a different approach instead of assuming that you’ve exhausted all possibilities.

Learn from your past mistakes, slow your roll and put a little more time in getting to know people instead of treating the bookstore like a singles’ bar. You’ll get much better results.

Good luck.

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Dear Dr. NerdLove:

I finally woke up out of dreamland a year ago mortified with the fact that, at the ripe old age of 21, that I am still a KV and haven’t been in a relationship with a girl. This is still the case today for many reasons, and it is something that continually eats at me every single day for multiple reasons.

The first is obvious: now I’m behind the bell curve and I’m so behind to the point where I cannot catch up to where I should be no matter what I do, where if I lost my virginity when I should have at 13 or 14 (like everyone else did) then people would actually desire me because now I have experience. I’ve tried dating apps and the like and the whole thing is just a catch-22: you need to date to get experience but you need experience to date. People ostensibly do not want to take their chance on people past their prime. I had one match that met up in person and when we discussed our past (on our third time meeting) she seemed fine with but we did not set up anything else past that and ended up choosing someone else over me. Meanwhile a good chunk of my friends are getting married and discussing futures with their partners. People actually *like* them because they have the experience. Other matches? I’m a dude on a dating app in 2025, of course I’m not going to get matches. Even when I do get matches, I’m often to the point of just ghosting them first because I know they’re going to ghost me eventually for not being good enough for them. It’s too late for me, might as well have some fun with it. Which I guess segues into my second reason.

The second is that discussing being a virgin at this late of an age automatically labels you an incel and is basically akin to social suicide. Perfection is not just expected out of people, it’s a requirement and even just hinting that you aren’t up to snuff with everyone else automatically disqualifies you from the game. I guarantee you that match I had in person still talks bad about me because she couldn’t fathom a man being a virgin at 22. How fucking delightful. I don’t even bother talking to women any more because I know the second they sniff out that I’m deficient in any way they’re going to bail for someone that’s better than me. Sure I go to social events often and whatnot, but I don’t bother (verbally) interacting with them because I know the moment I say something wrong I’m going to be outcast and forever left aside for someone better.

And the times they make the first move? I’m nothing more than an object for them to project their fantasies on and gawk at like I’m some fucking circus animal. Sure I’ve gotten told I’m attractive before and for what it’s worth I’m not completely physically deficient (5’11” and I’m going to the gym and lifting heavy at minimum 4 times per week), but it all feels fake and fragile. Even when I’m desired, I can’t accept it because I know it’s going to get taken away the second I don’t perform to their standards. And don’t get me started about the time I was sexually assaulted by a woman when I was in high school on a dare. How do you explain that to someone that you let someone do that to you? Because you don’t and people don’t give out sympathy for something like that. Because they couldn’t understand that and people don’t want to be associated with someone who’s now permanently marked as an undesirable.

I’m just fed up trying to navigate the dating world as someone who’s objectively inferior to other men and it is driving me closer and closer to suicide as an option. Sure I’ve been going to therapy (also something I couldn’t tell people) and have talked about this before, but it doesn’t matter because my weaknesses are all people are going to remember about me. Doesn’t matter my hobbies or my job or my lifestyle or my future career dreams, people only care about how to tear others down. It’s like everyone automatically knows how much of a fuckup I am and they know to steer clear. I’m tired of trying to hold up this facade of perfection and it’s breaking me down. How do I learn to be OK with being inferior to other men? Because I know dating is never going to happen because of that fact and I just need to be OK with it or die trying to understand it. I got this one chance at life and fucked it all up because I wasn’t perfect and I can’t cover that fact up anymore.

Doomed And Despairing

Hoo boy.

I’m going to be honest, D&D: I’m getting tired of answering this letter because I get variations on this letter on a nigh-weekly basis. Seriously, just check the archives. And as much as I feel like I should just set up a macro to post a standard replay and save myself the effort, I think I’m going to quit answering them and just pointing people to the years of answers of people saying the same thing, often with the same mistakes and absolutely bugnuts beliefs.

Let’s start with the obvious one: you’re 21 – hardly a haggard old man or even that far off the median age of losing one’s virginity. You’re hardly The Last American Virgin, nor are you particularly behind the curve. Your problem is that – like the chorus of your fellow travelers – is that you’re all singing from the exact same songbook and confusing baseless speculation and mistaking “just so” stories for reality.

Let’s start with “I should have lost my virginity at 13 or 14 (like everyone else did).” The only thing I can say here is [Citation Needed] because fucking hell dude, this is what happens when you believe the bullshit your classmates are spitting in the 8^th grade. The truth is that the average age for losing one’s virginity is 17, and that age is actually going up; in 2021, only 30% of high-school students reported having sex, a number that’s gone down consistently since 2011, when it was 47%. Just as importantly though, that’s the average, not the time when you’re supposed to.

In fact, I am going to hammer this part home: there is no age when you’re ‘supposed’ to have lost your virginity. The “right” age to lose your virginity is when you are physically and emotionally prepared and understand consent. That age is going to vary from person to person, based on their life and circumstances; it has nothing to do with their “worth”, their “value” or anything else.

I can also tell you that having had sex does nothing to make other people desire you. People can’t smell virginity or hear some special high-pitched hum that only players emit. Nobody is going to know how much sex you have or haven’t had until you tell them, and how they react is as much about how you roll it out as it is about whether they’re worth dating in the first place. It’s almost embarrassing to have to explain that to a grown-ass adult, because it’s such 13-year old “I got this from my stoner older brother” shit that I don’t think even you believe it. Except in this case, it’s pretty clear that this is you spending way the fuck too much time on incel forums and subreddits, where everyone’s got their Masters in Woman-Understanding From Just Trust Me Bro U. Your calves and quads must be huge from the amount of leaping to unfounded conclusions you’re doing. “She didn’t want to meet up again because we talked about our pasts” is an assumption and not even an accurate one. The odds are much better that she just wasn’t feeling it, in no small part because you spent most of the time waiting for her to dump you already.

Seriously, your emo phase was cringe when you were 15, when you’re supposed to be cringe while thinking that mild ennui is deep and meaningful; it’s painful to keep at it into your 20s.

Your friends aren’t desired because they’re experienced, your friends are desired in no small part because they’re not sad-sacks who disqualify and reject themselves constantly for bullshit reasons. You can’t even bring yourself to show up for people who actually want to give you a chance.

(Also if your friends – also in the 20-22 age range – are seriously talking families and marriage with their partners right now, then I will bet you a $20 Starbucks card that you’re going to see a 94% divorce rate among them in 5 years.)

But let’s go back to “discussing being a virgin gets you labeled as an incel” for a second. I’ll grant you that one conditionally… because you keep talking about it like it’s a big deal. Folks who don’t act like 21 is over the hill or treat virginity like a physical disability aren’t bringing it up to all and sundry. If you weren’t acting like being a virgin was an albatross around your neck and you were cursed to explain it to anyone who makes eye-contact for longer than 5 seconds, nobody would know, nor would they care.

You’re also giving yourself far too much credit to how important or significant you are in the lives of people you’ve known for a grand total of three hours or less. I can guarantee you – and will bet you cash money – that you have thought more about your failed match over the course of writing this letter than she has in the span of the last year. Believe me, she stopped thinking about you in less than 24 hours and far more likely in the amount of time it took her to order and drink a beer. To quote David Foster Wallace: “You will become way less concerned with what other people think of you when you realize how seldom they do”.

And to be clear: that’s not because you’re so insignificant that nobody thinks about you, it’s because everyone is way too busy with their own bullshit to give a damn about someone they matched with on a dating app months or years ago. Especially when there’s simply nothing there to respond to. I have had more matches and been on more dates – most of which went nowhere – than you’ve had hot meals, and I can count on the fingers of one hand how many of them I remember, with enough to count the original number of Green Lanterns in sector 2814. And the reason I remember those is because one date turned out to be a neo-nazi and the other had us chasing her coke dealer all over town. Your being a virgin does not rise to that level of memorable. This is entirely in your head, because it seems to have chased away every other thought you might have.

And that’s a running theme in every example you’ve given about how unloveable you are. All you do is go do things and then immediately sabotage any hope you might have and then wonder why nobody wants to talk to you. Yeah, I can’t imagine why folks aren’t lining up to talk to the anti-social dude who refuses to make eye-contact and glares at folks who might like him like they’re asking if he’s ever tried Hare Krishna. You’re projecting so much that you may as well as change your name to IMAX and you’re giving so many “it’s ok if you don’t like me, I wouldn’t like me either” vibes just in your letter that it’s going to have physical weight in person.

I’m not even sure why you’ve written in, because it seems like you’ve decided to just interact with fantasy versions of people where you get to write their responses for them instead of actually, y’know, talking to them. You’ve decided that people rejected you before you ever opened your mouth and when other people are interested you call them a liar and then take their walking away as proof that nobody could possibly like you.

Oscar the fucking Grouch has a better attitude than you and he lives in garbage.

So much of this is down to you refusing to believe anything other than the worst possible outcomes and insisting on only listening to people who confirm your worst beliefs because at some point you decided you prefer it this way. Your line about being assaulted is a prime example. I’m incredibly sorry that this happened to you but fucking hell you seem absolutely determined to make it impossible for people to try to reach out to you or even express sympathy that it happened at all. How do you tell someone about the time you were sexually assaulted by someone in school? By saying that you were sexually assaulted. Jesus hopfrog Christ, you didn’t “let” someone do that to you, that was done to you by a horrible person. The whole “let it happen” is toxic bullshit from choleric bulls and it’s one of the biggest reasons why men who’ve been abused or sexually assaulted never talk about it. Bad enough when other people blame you for being victimized by someone but doing it to yourself isn’t even masochism; at least masochists get off to the pain.

You know who has no sympathy for victims of sexual assault? Fucking horrible people. So if you’re only getting told that someone assaulting you in high-school is proof that you’re permanently stained, then we’re right back to “you need to be associating with a better class of person”, especially since I am completely sure that the only folks you’re associating with are other incels who just want to you to stay blackpilled.

And then there’s shit like “can’t talk about going to therapy”. What the fuck is this, the 70s? Fuck me running, I can’t count the number of shows where people going to therapy where characters going to therapy is both normal and a big part of improving their lives. Christ, the entire central premise of the fucking Sopranos is Tony Soprano going to therapy and how ass-backwards the rest of his mob buddies are about it.

And I’m going to be honest, I made an ugly snort at the line of “maintaining this façade of perfection” because, my guy, you aren’t maintaining shit. There’s no façade here, there’s just you being convinced you have an unreadable poker face while holding up a giant LED billboard that keeps saying “I HATE EVERYONE, ESPECIALLY MYSELF”. You are not the inscrutable enigma that nobody can pierce, nor are you an Oscar-caliber actor hiding your true self behind a character, you’re an obviously very sad, very lonely man whose bitterness and resentment is visible to anyone who glances your way. Other people aren’t mysteriously detecting your flaws, you’ve doused yourself in the same Bitter Apple solution people use to keep their pets from chewing on power cords like it’s Axe body spray.

The only person who’s decided that life is like this is you. At some point, you chose to believe this line of shit and you’ve held onto it for so long because the alternative is to recognize how much of your current situation is the result of your choices and yours alone. You have actively gone out of your way to push away anyone who might be attracted to you, want to be your friend or even help you, and then you complain that you’re lonely and unlikable. That’s on you, my guy. That’s your call, not anyone else’s.

If you want to let go of this misery and have a good life, you’re going to have to take responsibility and recognize that you did this. It’s going to suck. A lot. You’re going to have to peel away this shell of bullshit until you hit raw skin and it’s going to feel like you’ve set every nerve on fire and then you’re going to realize how stupid a decision it was to carry all that shit around in the first place. Then and only then will you be in a position to start being happy and actually accepting that people would like you if you would only fucking let them.

Until that day comes, you’re going to be wallowing in misery and it’s going to be by choice.

Your call.