I Want To Date, But I’m Not Attracted To Men My Age!

Estimated reading time: 18 minutes

Hey Doc,

I’m a 44-year-old, straight female virgin with both the curse and blessing of being young at heart. I’m one of those fat chicks who look pretty much the same from puberty till old age, which with fat filling out your wrinkles takes longer than most people. My junior high and high school pictures look like a dumpy 30-year-old already. Back when everyone else my age was at their hottest and skinniest, I was na turally overlooked and rejected. So I threw myself into nerdy hobbies and daydreaming and did my best to make an independent life for myself and not think too much about dating, partnered sex or loneliness. The fact I never wanted kids – I’m way too lazy and selfish, I like being able to spend all my spare time and money on fun stuff – made this easier.

Now I still look like a dumpy 30-year-old, which is terrible for 18, but pretty good for 44, when so many of those hot skinny girly-girls I felt so inferior to have had kids, gained weight, cut their hair, and just generally stopped caring. In the past few years, I’ve actually been asked out several times. The problem is it’s always divorced guys in their 40’s and 50’s. And this is going to make me sound absolutely awful, but… whenever a guy in my actual appropriate age range approaches or appears to be checking me out, I feel the same “Ew, creepy old man!” reaction as when I was in my teens or 20’s. It’s like not being married or having kids and having youthful hobbies really has kept me mentally and emotionally young. I feel like I’m still about 20-25 inside, and this means I naturally feel like guys in their 20’s, maybe early 30’s if they still look good, are my matches even when they objectively aren’t. I felt devastated recently when my secret crush, a cute 28-year-old male coworker, called me his “work mom.” When here I’d been fantasizing for the past 2 years about him asking me out! I smiled and said I loved being his work mom, but inside I was crying.

I know how unrealistic it is that a guy like that would ever date me. I know younger men are less likely to go for older women to begin with, and then I’m not the kind of older woman they want. I’m not a glamorous cougar…on top of being fat I’m dorky and low-maintenance. I get by on my own, but I’m in no position to be the one with the money in a relationship. I still rent and my car is a shitbox. I’m not even the confident, experienced erotic teacher some innocent, unconfident young guy might want…I’d need him to teach me!

If I want to experience love in this lifetime – a hope I thought I’d given up long ago, but now find rekindling – I know I need to look at guys my own age. But how do I reprogram my brain from this thing where as soon as a guy gets a beer belly, goes gray or starts losing his hair and grows a beard to make up for it, he goes into dad/authority figure/not sexy territory for me? A month ago I was asked out by the owner of a repair company I’d used. My friends are still screaming at me for turning him down. He’s a really nice, funny guy, he makes good money, he’s not even bad-looking for his age. But he is a portly bald man I’d guess is in his early 50’s, and it skeeved me to think of kissing or getting naked with him just as much as it would have when I was 20.

I know online dating might help me cast the net wider. But I’m so introverted and lazy to begin with, it’s hard to motivate myself to try when based on my real-life interactions, the guys I’m into see me as an unsexy mother figure, and I see the guys who are into me as unsexy father figures. Should I just conclude I’ve been alone this long, I might as well go the distance? Or is it actually possible to overcome this, and date a guy my age without feeling like I’m being creeped on by an “older” man?

Sincerely,

Forever 21

You know, F21, I can relate on the “I’m still young in my head!” But then my back goes to hell because my pillow was slightly too high while I was sleeping and people under the age of 30 look like they should still be getting birthday club offers from the local pizza chain.

My point being: I get the seeming dichotomy between one’s mental conception of themselves and the physical reality that says otherwise. Age may be in the mind, but your joints have their own opinions on the matter, and they tend to be a lot louder about it.

Sometimes literally. Especially when sitting down.

The issue here isn’t about an inability to find a relationship; as you point out, you’ve had lots of men asking you out – men who are actually age-appropriate for you! The problem is… well, you’ve kind of trained yourself into not wanting age-appropriate men.

And it is training, to a certain extent, the same as it is when men tend to pursue much younger partners; while youth comes with certain advantages with regards to having children, a lot of the desire for younger partners tends to be more acculturation than any sort of unconscious biological imperative. We, as a culture, have a tendency to lionize youth (when we’re not actively insulting them for acting young) as not just the height of beauty and desirability but as the only time when some things are even possible, and signs of age get treated almost like moral failings or fundamental flaws. Men, admittedly, have greater “allowance” to age and still be seen as desirable (in no small part because men tend to be the folks in charge of the media that perpetuates these messages) but youth still gets equated with aesthetics and virility.

So it seems to me that part of the problem is more about unpicking this particular knot in your head than being undesirable.

But before we get into how to start working on changing your mindset about more age-appropriate partners, there’re a couple things that need to happen.

The first is, simply, that you need to stop dragging yourself down. I know you think you’re just being honest or realistic, but the way you describe yourself and, by extension, the way you see yourself is part of the problem. The fact that you emphasize looking more mature as a negative is a great place to start; that “I look like I’m older than I am” attitude you were holding as a teenager is part of what’s set this negative feedback loop in your brain. You spent a lot of time saying “older = ugly = bad” along with “ugly = older”, and it seems like it was as much about yourself as it was about dirty old men who’re hitting on women half their age (or more).

Just as with the men who run themselves down for being “too ugly” to date, you want to change how you describe yourself and – importantly – how you treat yourself. A lot of the time, when we define ourselves as being unattractive, we treat ourselves accordingly – we dress for functionality rather than in ways we feel like make us look good, we carry ourselves in ways that broadcast a lack of confidence, our body language is less assured, less welcoming and more closed off, and so on. But attractiveness is as much in one’s attitude and mind as it is one’s facial features; if you treat yourself like you’re attractive, you tend to feel it. When you feel it, you’re more likely to see it and also to act like it… which other people respond to. So not bagging on yourself by describing yourself as “dumpy” or “inexperienced” is a big part of it… as is not using “older” as a negative.

Honestly, this is a time when I’d suggest more of a “MILF” framing for yourself, even though you’re not a mother. It’s not about the technical definitions, it’s about how you carry yourself, your attitude and the energy you choose to give off You can be that glamorous cougar, if you so choose, even if you think you’re not the “right” shape. Sensuality and sexuality is in the attitude, not necessarily in someone’s experience level. Getting in touch with your erotic side and knowing what you’re into and what gets you off and embracing it gives a hell of a boost to your sense of attractiveness, even when you’re a virgin. The overall attitude – embracing your age as part of your sexuality and the overall lack-of-fucks that often comes with hitting middle age – is going to help meeting people in general and with reprogramming your outlook so that you’re not squicked out by people in your age range. Everything is a lot easier when you’re not pre-rejecting yourself with an attitude of “it’s ok if you don’t want to date me; I wouldn’t date me either.”

(And it may also help with some of the younger dudes who catch your eye. Just sayin’.)

While you’re doing that, I think it’d be helpful to do some deep dives into why you were seeing older men as being a big pile of yuck. Sure, some of it was the importance of youth, but how much more of it was because these were guys looking for younger, less experienced (and thus presumably less wary) partners? Was that disgust reaction you developed equally split between appearance and their inappropriateness? Or was the majority of it aimed at the obviousness of how they wanted someone they thought would put up with their shit, when a woman their own age wouldn’t? Or, for that matter, their desire for a pretty decorative thing to prop up their ego, rather than an actual person and partner with agency?

I suspect that the “this guy is looking for someone pretty and compliant” was a bigger part of the reaction – and for good reason! A lot of the older men who want someone significantly younger than them tend to be looking for an ego prop instead of a person and that’s understandably going to give people the ick. But one of the quirks of the human psyche is that we tend to start with how we feel and justify the why of it afterwards. It’s easier to retroactively justify those feelings by going back and saying “look at that!” and treat physical qualities as being reflective of someone’s inner self.

The thing is: while that’s a helpful reaction when you’re younger, it isn’t necessarily meeting your needs now. What was creepy and squicky when you were a teenager is very different when you’re in your 40s, and so you’re still engaging in a form of self-protection that isn’t necessary any longer, but it still lingers.

So when you have this atavistic response you’re having to men your age flirting with you, you want to ask yourself if this is how you actually feel, or if it’s how you’ve taught yourself to feel? Is it because you’re still feeling that “ewww, you’re a predatory old man!”? If that’s the case, it can be worth taking a moment and asking if you’re actually getting that vibe from them, or if you’re just expecting to get it. Are they actually unattractive to you, or are you reacting to that initial feeling and finding reasons to justify it?

And if you’re not sure, see if you can put that initial feeling aside for a moment and try to look at him with less judgmental eyes. If you push past that initial sense of recoil and continue talking to him, what happens? Do you find that maybe your knee jerk reaction was incorrect? Are there aspects of them that are actually kind of appealing? Maybe he’s got a mischievous twinkle to his eyes or an infectious grin. Maybe those hands are a little more sensual and intriguing than you thought at first.

Or maybe they’re not. That’s fair too! Some people just aren’t attractive to us for one reason or another that’s through no fault of their own. They just don’t have whatever x-factor we need to be turned on by them and that’s ok. Not everyone’s going to be appealing to us.

Another thing that you may want to do is pay attention to the sorts of things you pay attention to when you’re in the mood to watch pretty people doing pretty things. As I said: a lot of culture focuses on the young, but maybe spending a little time with some older heartthrobs might help reframe some things for you. Maybe some George Clooney or Jeff Goldblum in proper silver-fox mode will do it for you. Titus Welliver might be your particular flavor of yum. You don’t need to be strapped into a chair while people do the Ludovico Technique to you while showing you endless episodes of The Golden Bachelor, but exposing yourself to people who are closer to your age who are being displayed as some prime salt-and-pepper goodness can help carve a new groove in your brain.

But very little of this is going to matter if you don’t start with how you see yourself, first. You want to be your own biggest fan and hype person, the person who’s telling you “you are a hot piece of ass, now go out there and get yourself someone who’s actually worthy of you!” instead of “well, here’s to hoping someone’s willing to tolerate us.” If not, it doesn’t matter whether you’re on the apps or meeting people in person; you’re going to have a hard time motivating yourself to actually put in the effort and you’re not going to believe the people who are interested.

Once you can see yourself as a tasty snack, you increase the odds that someone’s going to want to take a bite. Especially someone you might nibble on.

Good luck.

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Dear Doc,

I broke up with my ex, and my only female relationship, a few years back and took time to enjoy the solitude.

I have tried dating apps, but the nerd ladies I like either seem to leave me on read, or pass me over. What few ladies I know in Discord are either gay or in a relationship.

At this point, I can only come up with visiting nerdy locations like comic stores and asking ladies to go out with me, which is just bad form.

I was never the popular guy in high-school, and I was focused on my studies in college. My last relationship was literally pushed into me by her sister.

As I near 37, the very real fear of being alone is slowly creeping in. I don’t drink, I can’t be physically active, and I’m not religious, so visiting church events feels wrong.

Where do I meet single nerdy women?

Looking For Group

Ok, this is a two-part issue – one part logistics and one part skill issue. If you don’t deal with both sides of this particular equation, nothing’s going to work.

The first thing is very simple: how do you engage with your nerdy interests? It sounds to me like the majority of your socializing around your passions are conducted online, which is part of the problem. Don’t get me wrong: I’m not anti-online communities. I’ve a sizable number friends whom I knew for decadesbefore we ever met in person. But it’s very hard to try to start a relationship with someone you’ve only known online.

I know that people talk about getting to know the “real” person, or how they’re attracted to their mind and/or soul, but the fact of the matter is, we’re all meat robots and there’s no separating the importance of blood and flesh and hormones and pheromones. Love, as the sage once said, isn’t brains, it’s blood, screaming at you to work its will. There are a lot of factors that dictate who we’re attracted to that you can only pick up on when you’re in physical proximity to a person – even voice chat or video won’t convey those intangibles that make one person a yik and another a yum.

So, part of your solution is going to be to start going to places where your fellow geeks gather. Comic shops are one place, sure… but so are stores and coffee shops or even bars that host tabletop nights. Or you might see what events are being hosted by your local barcade or even singles events that’re hosted in your city.

The biggest thing is that you have to be willing to push at what you perceive to be your limitations and to think beyond that first guess. Not having any ideas besides the ones that seem most obvious isn’t an indication that you don’t have options, it’s a sign that you need to do more research and not just toss things aside out of hand. Geeks don’t tend to have only one interest or only gather at events that are explicitly labeled as being geeky. You might find your fellow geeks at a bar that does Murderbot watch parties or in cooking classes because they really got into Delicious in Dungeon, or at gaming events.

Similarly, the fact that you don’t drink doesn’t mean that a geeky-themed bar is off-limits. For one, nobody’s going to care if you’re having a Diet Coke instead of a Jack Daniels, or if you’re carrying a tonic water with lime instead of a G&T. For another, more and more bars offering non-alcoholic options besides sodas or lemonade; a lot of places have been going out of their way and putting as much care into their mocktails and non-boozy drinks as they do in to their beer and cocktail offerings.

(It should go without saying that if, say, going to bars would threaten your sobriety, then they’re clearly a no-go for you. It’s more about ruling out options because you think they won’t work, without actually trying them.)

But knowing’s only half the battle. The other half is actually connecting to people. And this is one that’s going to be more of a challenge for you because – as you said – you haven’t gone out and found a partner on your own. That’s something you’re going to have to work on… and it means adjusting your expectations accordingly.

See, I think part of the problem is that you’re expecting instant results – both in terms of “the women you are into will be present as soon as you arrive” but also “See hot woman – ??? – have girlfriend!” That’s something that’s going to hold you back, if you don’t pay attention.

For one thing, much as needing to move beyond just your initial (and only) idea of where to go, you need to think beyond who’s in the immediate vicinity when you go to a venue. Just because there’re no attractive and single people doesn’t mean that your trip was wasted. For one: not everyone goes on the same nights. For another: even if it’s nothing but partnered people or women who think you’re nice enough but aren’t interested in dating you… that doesn’t mean they don’t have friends. A lot of success when it comes to dating is about knowing how to network and just meet people. Much as in business, the guy you met at a work conference may not be the guy who can offer you a job or invest in your start-up… but they may know someone who is.

For another, there’s the matter of how to connect with folks, even if they’re hot and single. If you’re rolling into a place like a horny Pac-Man trying to get to a power pellet, people are going to react badly. Part of the reason why going to a comic store and just hitting on the women there would be a bad idea is that this is not how most people start relationships. Very, very few people start dating a stranger they met twenty minutes ago. Even on dating apps, there’s a period of talking, establishing mutual chemistry and trust before that first meet up, never mind a date.

Similarly, people aren’t necessarily going to the comic store to get dates. They’re there to get comics, and maybe to socialize with other comic lovers. And while some of them may well be single and looking, that doesn’t measn that they’re going to be in a socializing headspace immediately. Rolling in like it’s a singles bar is going to be incongruous at best, and people are going to think that sort of behavior is weird.

This is part of why I talk a lot about dating slow – that is, taking a more measured pace and getting to know people over time. Not just women – people. Becoming a known quantity at the TTRPG night or the pub trivia or the coffee shop is incredibly helpful when it comes to building your social, in-person network; people who’ve seen you and interacted with you regularly get to know you, feel comfortable with you and can vouch for you to others; they’re providing social proof that you’re a good person and worth getting to know.

Meanwhile, taking time to get to know people and just talking – even when they’re folks who you want to date – gives you an opportunity to connect with them, find out what you have in common and see what they’ve got going for them besides their looks. When you first meet someone, you know nothing about them besides what’s on the surface. And while they may be hot as hell and rocking a Ghost-Spider hoodie… you still don’t know anything about them. There may well be hidden aspects that leave you going “yeah, not even with a borrowed dick and Sabrina Carpenter to do the pushing”.

And by focusing on getting to know them, rather than trying to get a date also takes the pressure off to perform. Instead of trying to speed your way to getting her number and becoming incredibly, painfully self-conscious, you can just be in the moment and vibe with them. This not only means that you get to find out if they’re worth your time, but they get to know what makes you uniquely you – something that matters a lot to attraction, especially attraction built over time.

So I’d recommend that instead of taking a shotgun approach of firing off rounds at every attractive single nerdy woman you see, you give yourself time to just talk, make connections and see where things go. If, over the course of a conversation (or two or three or five…) it seems like there’s a mutual vibe going on, then it’s the most natural thing in the world to say “hey, I’m really enjoying talking to you; is it cool if I add you on WhatsApp?” or “By the way, there’s a video-gamed themed art show opening at $_GALLERY this weekend that I was going to go to, and I think you’d really enjoy it. Would you like to go with me?”

Do your research, find where your fellow geeks gather and spend time there. Just hang out, talk with folks and get to know people. Before long, you’ll be meeting many special someones, and you’ll have laid the groundwork to asking them out on some awesome dates.

Good luck.