Why Should I Bother Dating In The First Place?

Why Should I Bother Dating In The First Place?


Estimated reading time: 14 minutes

What’s up, Doc?

I’m like a lot of your readers. Male, mid-20s, complete virgin, probably have undiagnosed AuDHD. Never had more than a first date, never been kissed, never so much as held hands or had long lingering gazes with someone of the opposite sex. Like a lot of other folks I started reading you and other dating coaches because I wanted to finally get a date. But after everything I’ve read I’m not sure why I’m bothering.

It just seems like I have too much working against me to ever get a relationship. Like, it’s clear nobody would want to date me because nobody has before. I’ve seen too many people on Reddit or TikTok talking about how they don’t want to have to teach their boyfriend to chew their food and I’m not going to be any good in bed, so why would anyone take the chance on me? And then I read your site and other people talking about how your first relationship is probably going to fail and then I begin wondering why I’m even trying in the first place if it’s just going to end with my getting dumped. Like, what’s the point of finding a girlfriend for the first time if she’s just going to break my heart?

Maybe if I’d started dating in high school like everyone else I could’ve gotten my starter relationships out of the way and I could get a real girlfriend but instead I’m just an overgrown manlet and I don’t see how that’s going to change.

Obv. I’m hoping I’m wrong because I’m writing to you but I just don’t see how this could possibly work for me. Is there even a point in my trying or should I just start saving my money for when we get sex robots?

Holding Out For The Robots

I’m going to let folks get a glimpse behind the curtain, HOFTR: I picked your letter in part because I get versions of this question almost as often as the “I’m Too Ugly” questions and as tempted as I am to just respond with “stop treating randos on TikTok as authorities in anything” and call it a day, I actually want to take this head on.

So I understand that it’s very easy to feel like dating is a catch-22; you hear from folks who don’t want to be a guy’s first, but how are they supposed to have any experience when they’re virgins? Some folks assume that there’s a window of acceptability – usually about 5 or so years before their current age – and if you miss that, you’re fucked. If you don’t ever actually think about it, this might make sense. But that’s not how relationships actually work. These are just various toxic ideas about masculinity and being a man, laundered for wider consumption, often by people who’ve bought in whole-heartedly. You haven’t had sex, ergo you’re not a “real” man. And women – who are still the supposed gatekeepers of sex in these narratives – wouldn’t want to “waste their time” on a guy who can’t please them or doesn’t know what he’s doing, so clearly guys without experience are just SOL.

The problem is that this assumes a lot of facts that aren’t in evidence and relies on some very mistaken ideas about love, sex and relationships.

This mindset teaches people to act as though relationships work like leveling up in an RPG; get enough experience points and you automatically get better at oral and foreplay and if you reach the level cap you get the rank of Hierophant of Sex and never have to worry about getting dumped ever again. But that’s not how any of this works. Being a virgin doesn’t mean you’re doomed to be a lousy lover any more than having had lots of sex means you’re good at it. I mean, any woman with a moderately active dating life is probably laughing at the idea that someone is going to be good in bed just because he’s had sex before.

But more to the point, it also posits that dating and romantic relationships are unique beasts, entirely different from any other human connection we have. And it really isn’t. If you’ve made friends before and maintain those friendships, then you know pretty much all the basics of dating and romance. Sure, you’re (probably) not hooking up with your friends or spending a Sunday night arguing about what to watch on Netflix or having discussions about whether you’re spending this holiday with your parents or theirs… but the mechanics of building and maintaining a friendship aren’t that different from a romantic or sexual relationship. The difference is one of intent and outcome. Spending time with your friends, remembering important dates, giving them time and attention and getting time and attention from them? Showing them that you care? Yeah, you’re going to be doing all of that with your romantic partners too.

But what about all the people saying that they don’t “want to teach someone how to chew their food” (a term I hate, for the record)? Well, first, those people aren’t the majority or even a significant minority. They’re just the folks you notice and give the most attention to because what they say feels personal to you. Yes, people who think like that exist and that’s ok; people are allowed to set their standards where they want and decide that any particular thing is a deal breaker. But all that they’re doing is indicating that they’re not someone you want to date in the first place. If someone is willing to pass on a great and fulfilling relationship just based on the idea that you haven’t stuck your dongle into enough willing ports, then that’s someone who’s self-selected out of your dating pool.

I mean, imagine if they someone was declaring loudly that you were unfuckable because you had the wrong hair color. Not for any other reason, just you’re a ginger and as far as they’re concerned, only brunettes know how to fuck. Would you honestly be upset at that person for rejecting you out of hand or would you just roll your eyes and keep moving?Why would waste even a second of your time on someone who thinks like that?

But let’s take the hyperbole down a notch and, instead, focus on the idea that your not having some particular quality really is a person’s deal breaker. Maybe it’s height, maybe it’s age, maybe it’s sexual inexperience. The fact that you don’t match their preferences doesn’t mean that they think less of you or that this is proof that you’re flawed somehow. I’m sure you have your own preferences and people that you don’t find attractive for whatever reason. You, presumably, don’t look down on them for not being your type; you’re just not into them. If you can refrain from viewing people you aren’t into with disdain, why can’t Sally in Accounts Receivable? The whole idea that someone being insulted by the Not Hot being into them is much more the domain of terminally online men, not reality. Especially when we’re talking about just asking someone on a date and not, y’know, being the office sex pest from an 80s sitcom.

Are there people who think that way? Sure; there’s nearly 8 billion people on this planet. The odds are good that there’ll be a couple of folks who really are that up their own ass. Does that mean you need to take them into consideration? FUCK no.

Now with all that having been said, let me take the “don’t want to teach someone to chew their food” thing seriously. What you’re almost certainly missing isn’t that they’re saying “I don’t want to have to hold someone’s hand and coach them on how to please me”. What they’re saying is that they don’t want to have to play Fuckable Mommy. And let’s be real: that’s what a lot of guys expect. Even guys who don’t realize it.

One of the issues with how men are socialized is that our emotional growth, our ability to communicate or even just be emotionally available is frequently stunted. The whole “women are such mysterious creatures”/men-are-from-mars-women-are-from-venus shit is really about generations of men who’ve never bothered to actually learn how to listen, how to communicate, how to manage their own emotions or how to handle their own shit. Entire generations of men have been taught to expect women to do all the heavy lifting in their life, especially for anything that isn’t important to men. This is part of why the whole Manic Pixie Dream Girl idea is toxic; it’s one more example of men expecting women to facilitate their growth and then reward them with blowjobs.

But if you’re someone who generally has his shit together, is at least willing to take responsibility for his own emotional development, who knows how to communicate (which is different from talking) and how to listen (which is different from hearing)? Then they’re not talking about you. And let’s be honest, the bar is pretty damn low. If you’re showing that you’re making an effort and actual progress, you’re doing better than many.

The other reason why they’re less likely to want to date someone with little or no experience? They don’t want to be somebody’s starter relationship. While not everybody goes into each relationship assuming it’s their last, what they don’t want is to be dating someone who’s going to have a foot out the door. One of the things about committing to a relationship – even a non-monogamous one – is that you’re closing the door to other relationships. Every relationship is a compromise between what you want and what you’re willing to not get in exchange. Again, this is true, even in non-monagmous relationships; you may not be expecting one person to meet all your needs, but there’re a lot of folks who aren’t going to want to be in a relationship with someone who’s committed to someone else already. 

A lot of folks – mostly  but not exclusively men – get caught up in the FOMO of dating: are you sure you want to settle here? What if you meet someone else who’s even hotter? Or more likely to have wild crazy sex or who is more likely to make your bros jealous? There’s a not-entirely-unreasonable belief that someone who’s been around the block a couple times isn’t going to always be looking out to the horizon and wondering if maybe they could do better. The idea is that someone who’s inexperienced is going to be more likely to have regrets for not having an idealized slut phase or didn’t date around “enough” and is more likely to decide they want to “trade up” or something.

The thing is: this isn’t about experience. Shit, I’ve folks who were on their fifth or six marriage because they were always looking for an upgrade. What this is about is maturity and honesty – both knowing and accepting that any relationship means not getting everything you want but also being able to be up front about what kind of relationship they’re open to having and what they aren’t. Someone who knows and owns that they want some period to sow their metaphorical wild oats shouldn’t be making commitments to someone who expects and wants exclusivity. They would be better off looking for something casual… but it’s easier to find someone who wants commitment, and so they take that instead. Some are doing so in bad faith, some are doing so in what they think is good faith, but the results end up being the same: they decide they need to go explore their options and bounce.

But what about you? How are you supposed to know if you want to commit for life to someone when you haven’t had a lot of relationship experience? Well… nobody says that you do. Nor do you need to know exactly what you want. I know I’ve folks shit  for being disingenuous about “looking for casual, open to long-term”, but there’s nothing wrong with saying “I can’t guarantee forever, and I don’t know what the future holds, but I’m interested in finding out with you.” There’re people who won’t want that, but that’s ok. You want people who are on the same page as you, not someone who will say what you want to hear in hopes of changing your mind. Nor do you want to promise things that you know at some level you aren’t actually open to. But if you can say “here’s what I am open to and what I offer, what about you?” Then you’re a step ahead of a lot of people.

And what about “your first relationship not likely going to last”? Well, here’s the thing: this isn’t about the inherent failure of one’s first relationship.  Recognizing that your first relationship isn’t likely to be your last isn’t about prepping for failure, it’s a matter of recognizing that you can’t predict or control the future. Every relationship ends; it’s just a question of how. Couples break up, partners die… hell, sometimes shit can happen in your life through no fault of your own that will end up making it impossible to stay together even if you love each other to pieces. Recognizing that doesn’t mean that you’re being defeatist and pretending that this isn’t a possibility doesn’t mean that you love your partner more.

To make an incredibly awkward comparison: when you get a cat or a dog or any other pet, you do so knowing that you’re also buying into the possibility of a future without them. It’s not guaranteed that you’re going to out-live them, but you know it’s a possibility, and you want to try to ensure that this day is as far away as possible. But you’re also acknowledging that life with them and what you get from having them in your life means that you’re willing to face that potential pain in the future.

Recognizing that your first relationship is probably not your last is also about advising the young, the ones who have the enthusiasm but not a lot of experience under their belt, that relationships early in life often don’t last because you’re still learning who you are. Part of why, for example, high-school relationships rarely last past graduation is because that’s often the first time they’ve found themselves entirely on their own. They’re now discovering who they are beyond the child of their parents, exploring different sides of themselves and frequently learning things about themselves they had no way of knowing up until then.

You’re never the same person one day to the next, but never so different as when you transition from being a teenager to an adult. That often means that relationships that were right for you at that time aren’t going to be right for you in the future. That doesn’t mean that the relationship failed, just that it reached its natural conclusion. You both finished that chapter of your stories and now you are moving to the next… and those stories no longer unfold together.

Not having a lot of dating experience isn’t a detriment or a marker of inferiority. If it’s a mark of anything, it’s more that you don’t know (yet) what you don’t know. Gaining more experience will help you navigate more experiences or how to handle some situations with greater skill and fluency, but nobody can predict or prepare for everything life brings. The biggest benefit to experience is recognizing that you don’t know everything and letting that give you greater flexibility when shit hits the fan in ways that you could never have imagined.

So do you go into every relationship assuming that it’s going to end? No. You go in knowing that it’s possible, because nothing is guaranteed. You go in knowing that the length of a relationship doesn’t define its worth, nor its success; a short term relationship can be a success, while a marriage that ends with both people dying at the same time could be a complete failure. But you go in with good faith and intentions and a willingness to face what the future may bring together, rather than with one foot always out the door.

What does this mean for you? It means acknowledging and owning that yes, there’re things you’re going to be learning as you go. But that’s true for everyone, not just the inexperienced. It means ignoring the people who aren’t right for you and looking for the people who are – and I promise you, there’re far more of them out there than you think. It means doing your best to be self-aware and mindful, to do your best to ensure you’re pursuing the relationship you want, not what you think you “have” to accept. It means going into a relationship realizing that there may be an end, but resolving to love as if there isn’t while also doing your best to savor each moment and not take it for granted.

What it doesn’t mean is taking other people’s bullshit onboard. Especially bullshit that’s handed out third hand, whose source is “just trust me, bro”.

Not having a relationship, like being a virgin, doesn’t say anything about you other than there are experiences you haven’t had yet. It’s no more a gauge of your worth or value than being left or right handed. And the vague possibility that other people do believe it doesn’t mean that you have to. You’re allowed to recognize and disregard bullshit when you see it, no matter how much it aligns with your worst fears.

Good luck.