Relationships Talk

Hello my motile macaques of love, and welcome to Ask Dr. NerdLove, the dating advice column that’s mankind’s last, best hope for pizza. This week, we’re talking about the trials of finding love, when everything seems to be working against you.

What do you do when you’re seemingly invisible to people your age, but younger folks think you’re exactly what they’re looking for? And what do you do when the people you meet think you’re good enough to bang but not good enough to date?

Fire up the ovens and grease up the Vorlons, it’s time to do this thing.

Hi Doc,

I have a weird problem and I don’t know what to do about it. I recently emerged from a period of antisocial hibernation after a bad relationship, in which the vast majority of my social contact occurred during online gaming and Discord. I’m 40, and I guess I just assumed that this meant the end of my dating life. I had braced myself to just sort of blend in with the woodwork—to take the role of friend in people’s lives and not be the target of any sort of romantic overtures. Especially after what my ex did to my self-esteem during my last relationship (he wrecked the fuck out of it), I figured that I was just destined for being a cat lady.

Holy shit, was I wrong.

My problem is that right now, for reasons I don’t understand, the vast majority of the incoming attention I’m getting is from men in their early to mid twenties. I keep telling them I’m too old for them, but this doesn’t seem to discourage anyone. As nice as it is to have that attention, I feel horribly guilty at both enjoying that attention and at the fact that I also find them attractive.

I don’t want to be one of those perverts who takes advantage of younger people via the wisdom that comes with experience or just the trickiness that comes with age, and I don’t understand why they’re interested in me.

I mean, maybe I’m making too much of this, but I assumed that if I was ever going to get romantic attention from anyone again, it would be someone my own age. I appear to be invisible to men around my own age, and it’s not like there’s any future in accepting dates from men that much younger than me. I’m really not interested in no-strings-attached or a fling. If I’m going to date someone, I’d like it to have the potential to be something long term.

At this point, I feel awful about the whole thing. My friends have been joking that they need to change my ringtone to “Mrs. Robinson,” and every time someone makes that joke, I cringe. It makes me feel like some kind of van dwelling pervert.

It doesn’t help that my hobbies involve gaming and programming, and that I’m lonely. I’ve branched out into monthly Meetups for various topics in programming, but once again, I’m invisible to men my age.

To the best of my knowledge, I’m presenting like the age I am. I tend to dress comfortably unless I’m coming straight from the office, so they’re meeting me either in yoga pants and a t-shirt or in a blouse and slacks. I don’t dye my hair or wear makeup, generally, and while I do get regular workouts, I could stand to lose a few.

The feedback I’m getting from those twenty-something men is that I’m easy to talk to, if it helps. I generally find people easy to talk to, and I don’t mind listening.

I’m hoping that maybe you have some good advice, or some way to put all this into perspective. It’s probably not that big of a deal, but it’s really bugging me.

—The Reluctant Mrs. Robinson

Let’s start with the easy part first: the reason you’re not getting as much attention from men who’re more age-appropriate to you is, honestly, a lot of the single men your age are focused like lasers on trying to get the women they were into back when they were in their twenties.

Some of this is societal. We all spend a lifetime swimming in media that tells men that they’re supposed to be virile sex-beasts, that the only women worth pursuing are in their 20s or younger and that women who’re older than 35 don’t exist as sexual beings. The Hollywood leading men we grew up watching are allowed to age, but their romantic pairings aren’t. I can count the number of movies where the male and female romantic leads were within five years of each other on the fingers of one hand. (It’s The Thomas Crown Affair, for the record)

It doesn’t help that part of the reason why older men tend to go for younger women is that often the women their own age know better than to put up with their shit. A twenty-something might not know better; a forty-something will call them out right the fuck then.

On the other hand, we also have genres and subgenres of porn involving every permutation of “older woman/younger man” that you care to think of, ranging from moms to best friends’ moms, to teachers, to peeping-toms who get lucky. And even then, the “MILF” category starts with 30 year olds in the titular roles.

It doesn’t help that there’s a stereotype among young men that older women are not only more experienced but also more desperate. Some guys in their twenties like the idea of going after older women because — in the words of Ben Franklin — “they are so grateful.”

Now in your case, I suspect that there are other factors involved. One of them is that you’re likely less intimidating to many younger men than girls their own age. This is a sort of left-handed compliment. Because you’re older, you’re less likely to be playing the same social games that they may encounter at bars or clubs. As someone who’s been there, done that, and bought the t-shirt, you’re far more likely to have your shit figured out than their peers and are more likely to be straightforward, even blunt about what you think and what you want.

And, to be perfectly honest, they may find you less intimidating because they see you as having less social cachet than women their age. It’s easier to talk to you — even flirt with you — when they don’t feel like they have to play weird status games. So I’m not terribly surprised that you’re seeing more would-be paramours who’re only barely older than the whiskey behind the bar. The question is: what do you do about it?

I’m going to be frank here: your biggest problem is ultimately going to be the pool of potential dates. The age-appropriate men out there who are interested in women around their own age are going to be less common than the men who want to prove they’re still the guy who can get a younger woman. Those men aren’t unicorns — hell, they’re not even okapi — but you’re still going to have to go through a lot of dudes who’d rather date younger women to get to them.

If you were looking for a fling in the meantime, then I’d say hell with it, grab one of these young’uns and have a blast. You may be taking advantage of them, but they’re the ones lining up to volunteer to be taken advantage of. Don’t forget, we’re not just people, we’re also pieces of meat who occasionally want to be used.

If you’re looking for something committed and long-term… it’s certainly not impossible that things could work with a younger man. It doesn’t get nearly as much play in pop-culture (except as an oddity to be boggled at) as the older-man/younger-woman pairings we see pretty much constantly, but those sorts of relationships do happen far more often than you think. The old saw of “half your age plus 7” gives you a decent rule of thumb for how low you could conceivably go.

But if you want someone who’s more age-appropriate, you’re going to have to take an active hand in finding them. If you want to maximize your chances of finding someone who’s not only your age but also interested in you, then you’re going to have to put in the effort.

Now, it sounds like you’re looking for companionship and connections as well as potential romance. In that case, leveraging your interests to develop your social circle is a good idea. MeetUps are a good start for finding people who like the same things you do, but it’s easy to get tunnel vision. It may help to broaden your scope of where you’re going to meet people; just because it doesn’t match your specific interests doesn’t mean that it may not be worth checking out. Finding things that are bankshot related to what you like can be a great way to meet people you’re compatible with and expand your horizons.

If you’re a gamer, then finding some tabletop or board game groups might be a good way to go. While tabletop gaming’s having a renaissance right now with Critical Role, HarmonQuest and other D&D related podcasts and shows, the average tabletop group tends to be slightly older. You’re more likely to find 30-somethings who’re into RPGs than 20-somethings.

You may also have luck going to events that are team-based, like Geeks Who Drink pub-quizzes. These often work better for socializing because you’re working together towards a goal. You have to communicate with one another instead of focusing on the few people you know (or want to bang).

Don’t forget events specifically for singles, while you’re at it. There are often singles mixers specifically for people your age, where you can meet folks who are explicitly looking for potential relationships.

I wouldn’t neglect dating apps, either. Most people who are successful at finding partners — regardless of their age — tend to approach the issue on multiple fronts. Getting social is good, especially because it makes you a more well-rounded, interesting person. But dating apps let you date at your own pace, checking out and approaching people when it’s convenient for you. As with meeting folks the organic way, you are going to find a lot of men who want something younger. In fact, you can spot ‘em by the fact that their low end of “looking for” is half their age but the oldest they’ll go is maybe three to four years above them. By that same token, you’ll also be more likely to find folks who want the same things you do… and who are looking for someone your age, too.

That may be your best bet when it comes to finding someone to date, not just hang out with. After all: if you want to go track down an okapi, you can go wandering around the savannah at random… or you can stake out the watering holes and wait for them to come to you.

Good luck.

Dear Dr. NerdLove,

I read your articles since many years and I am increasingly impressed with your wisdom, humanity, and true insight on the topic. Side note, to you and all the straight nerd men reading, your level of emotional intelligence, respect towards women, and nerdy sense of humour is a major turn-on for a geeky sapiophile girl like myself. Anyhow, I thought I could use your clever advice on a thought I have running in my head since a few months:

Setting: I’m a late thirties nerdy punk woman. I have always been naturally eccentric but I wasn’t typically “girly” in style before teenage-hood bullying. Physically, although I truly hate rating humans, especially for appearance, I would describe myself maybe as a 4. After some harsh comments and being generally ignored by high-school boys when I was developing into a flat chested woman, I discovered that by looking more feminine, growing long hair, wearing tight clothes, dresses, skirts and makeup, suddenly, I had no problem getting interest from the people I liked.

So, for over 20 years, I have been usually wearing dresses and skirts (I also found this more comfortable to be fair), and makeup everyday, most days even while sleeping! Very few people have seen me without makeup due to my insecurity without it. I don’t wear much of it, but I believe I am a good enough designer to maybe have upped myself from a 4 to a 6-7 (again, don’t like numbers but..) with my clever use of colors and choices of clothing.

But now, after several long-term relationships and (too) many hookups (I am now officially completely bored by hookups), I am realizing that I often get frustrated, disappointed and heartbroken because I have the impression most people interested in me (beside my mom and my gay friends) were/are only or mostly interested in me for sex. For example, if/when I made it clear the possibility for sex isn’t there (or isn’t there anymore) but I’m really interested in friendship, suddenly zero-interest-ghosting-level, even with people that were friends before.

It is also very annoying because personally I need to really know/trust a person, ideally become friends first (take that, stupid concept of “friend-zone”) to feel any sort of love. And if sex, or even just a kiss, is pushed on as early as date number 1-3, there is zero time to know somebody before.

So, I searched for the problem’s common denominator, which is me. I started thinking that if I put so much effort in always looking perfect and pretty I couldn’t act surprised that I only attracted people solely interested in my looks and who were disappointed in me if one day I wore a t-shirt for comfort. I even had a 7 years (ex)partner complaining in couples therapy he found me less attractive now, because I wore “less” makeup (when we met I was so insecure I woke up in the middle of the night to re-glue my fake eyelashes!). After a few years of common life, I dared to relax a bit on retouching makeup in the middle of the night. I’m okay with taking reasonable care of myself, but looking our total best self 24/7 for 7+ years is fucking exhausting.

I am now single, per choice (or lack of the right choice), for the longest period of my adult life and I truly appreciate the “stress-free” side of it. I promised myself I would not have sex with anybody else unless I am sincerely (and reciprocally) in love first, and I am totally fine with the wait. Waiting for true reciprocal love is worth the wait to my opinion, but I would be a little sad if it never happened.

I am thinking, for the first time of my adult life, of completely stopping wearing makeup and starting dressing up more “sloppy” and in a more “masculine” style. I am thinking that if I don’t dress pretty at all I might be able to “filter out” the people only interested in me for my look or wanting to try an “exotic looking nerdy-punk” in bed once for fun. Although I know I will not have as much (maybe none) people interested in me, at least, if it happens, I will know it’s for the real me and not because of a sudden temporary attack of manicpixiedreamgirlitis. I’m also super hyper sick of constant catcalls in the street, upskirting bullshit, PUA who thinks they are being subtle in bars, and wasting over one hour per day on styling my body.

However, I do really miss my colored hair, comfy skirts, and general natural colorful personality. I feel like I’m now wearing a disguise of some sort and can’t be myself or feminine or flirty without having to deal with all this cultural gender bs and unwanted sexual propositions that don’t take no for a stop.

Questions: How can I attract people who would love/like me for my brain (not zombies though) and not my appearance? How can I find friendships with nerdy guys sharing my interests who won’t just talk to me in the hope of eventually banging me? How can I avoid meeting men who only want to be saved by a “manic pixie dream girl” and then throw her away when they feel sufficiently saved? How can I still feel like I look like my colorful interior self without attracting jerks, catcallers, and dangerous dates (yes, that happened too)? Do I have to stick with this plain brown and black “disguise” to project the “right” impression until I find true love and true friends?

Thanks for your time and general awesomeness <3

-Real Outsider Girl Eversearching Realloveandfriends

First things first, ROGER: you can’t control other people. There’s literally nothing that you can do to prevent thirsty dudes from coming after you under false pretenses or dickheads from cat-calling. Women have gone out looking like five miles of bad road and still have dues yelling at them. Assholes gonna ass and horndogs gonna horn.

And trust me: there’s really no force on this earth more determined than a dude with a boner, a mission, and no social skills. They’re like priapetic Terminators. There’re women out there who’ve done social experiments on social media to see just how crazy they can pretend to be before horny dudes quit trying to get with them. SPOILER ALERT: it didn’t work until someone got to Just Monika levels of crazy. And honestly? Not always then, either. Welcome to dating, carry a whip and a chair.

But while there’ll always be ones who can’t catch a clue with both hands and a head start, you can filter out the more obnoxious ones — and draw in the ones who are more compatible with you — by embracing your authentic self.

One of the mistakes that people make — especially people who feel that they’re not conventionally attractive — is that they tend to try to minimize their uniqueness. They want to be as broadly appealing as possible, the better to have as large of a dating pool as possible.

The problem is… broad appeal also tends to be shallow appeal. You get more interest, yes, but it’s often not the interest you want, nor does it tend to last. As much as I’m not crazy about folksy quotes, it really is better to be someone’s shot of whiskey instead of everyone’s cup of tea. A dozen dudes who think you’re ok isn’t going to be worth as much as a couple of guys who really dig what you have to offer.

So my suggestion is: dress how you want to dress. What look is the most authentically you, the outfit that corresponds best with your personal archetype and makes you feel like a sexy bad-ass? Let your inner self come to the surface, whether she’s got a partially shaved head, colored hair and combat boots or a sundress and a hat.

Your look may be polarizing. Good. That’s what you want. You’re better off with a more divisive look, because it will help turn off the folks who can’t handle you. The ones who stick around? They’ll be the ones who can handle realizing that women wear makeup sometimes, gasp shock quelle horreur.

The other thing to do is keep and maintain strong boundaries… and be willing to enforce them. By now, you know what behavior you are and aren’t willing to put up with. That’s a strength, as long as you use it. If a friend is starting to give you Nice Guy vibes, then call them on it. Part of why guys go with the Schrödinger’s Date routine for so long is because many women are still socialized to go along to get along. They don’t want to risk being rude or hurting the poor guy’s feelings. And since the Nice Guy will tend to fall back on the ol’ “Whaaaaat! No, no, you’re imagining things, what do you mean ‘I’m trying to turn this into a date’, don’t be absurd!”, women let them get away with it.

Like I said: you can’t stop would-be Nice Guys from approaching or pretending to be your friend. However, not being willing to put up with dudes trying to pull the Platonic Best Friend Back Door Gambit cuts down on the number who will try.

Same with guys who want a Manic Pixie Dream Girl to save them; don’t go for the ones who don’t have a personality strong enough to match up with yours. If they don’t have a lifestyle that’s already compatible with yours or a personality that can keep up, then let them find someone who’s willing to take on a project. You’ve had your share of fixer-uppers, you know that you want a turn-key relationship that’s ready to go. You may not be able to filter them out entirely… but you can at least keep their presence in your life to a minimum.

I will warn you, however: being your authentic self and giving up that old plumage and camouflage is hard. You’re going to feel panicked at the thought of it. You’ll drive yourself to distraction wondering “what if nobody likes me?” and want to run back to the security of the known.

This is just your jerk-brain talking. Our brains are lazy and don’t like change. Doing things differently requires effort and energy and a willingness to embrace the unknown. What we already know is easier and more comfortable… even if it makes us unhappy. Your brain will throw doubt and fear and anxiety your way to try to push you back to the routine you’ve been in for all this time, simply because you’ve been doing it for so long.

Ignore it. Push past it. Draw yourself up to your full height, think murderous thoughts and walk through it all until you get out the other side and realize how free you feel. And then revel in your authenticity, like you can fully exhale for the first time in forever.

It may take you some time to get used to it… but you will. And when you do? You’ll find your kind of dude out there, waiting for you.

Good luck.

Are you a woman who has dated younger men? Have you dealt with trying to be someone you aren’t in order to date? Share your thoughts and experiences in the comments. We’ll be back with more of your questions in two weeks.

Ask Dr. Nerdlove is Kotaku’s bi-weekly dating column, hosted by the one and only Harris O’Malley, AKA Dr. NerdLove. Got a question you’d like answered? Write doc@doctornerdlove.com and put “Kotaku” in the subject line.

Harris O’Malley is a writer and dating coach who provides geek dating advice at his blog, Paging Dr. NerdLove, and on the Dr. NerdLove podcast. His dating guide New Game+: The Geek’s Guide to Love, Sex and Dating is available on Amazon, iTunes and everywhere fine books are sold. He is also a regular guest at One Of Us.

He can be found dispensing snark and advice on Facebook and on Twitter at @DrNerdLove.