Twelve Things You'll Learn as a Woman Dating Men in Her 20s

An emotional journey of contradictions.
Hannah Ewens
London, GB
photos by Emily Bowler
dating in your twenties
Photo by Emily Bowler

This article originally appeared on VICE UK.

In your early 20s, you know nothing about sex, dating, and relationships. I hate to sound condescending, but as a 27-year-old woman, I now know this to be true. Women in your 30s or older reading this and smirking that I too know very little: You are correct. I freak out when someone stops telling me I'm amazing every five minutes, have never seen a relationship to its second birthday, and have the commitment issues of a stray cat. But that's the point: You have to live through all sorts of romantic relationships to get it.


Your 20s, I'm afraid, are where you do a lot of the painful learning. As a girl, you're evolving from someone who keeps their bra on during sex to a Self-Assured Adult Woman (SAAW). If you're a nascent SAAW dating straight men, you'll have to deal with varying degrees of emotional intelligence—hello, incels: Yes, men are slower to develop than women—meaning you'll inevitably swing from belief to belief about the nature of relationships. You'll stubbornly consider each truth about men and/or dating to be gospel, all until the next disorientating experience. It's fun! It's a fun time!

Here are those stages. Here is a timeline of everything you'll believe as a woman dating men in your 20s.

High School 'Love' Is a Lie

You spend a happy year-and-a-half googling "famous couples together since high school," taking performative cues from porn and pretending to orgasm from poor quality penetrative sex. Then your high school/freshman year boyfriend either cheats on you or sits you down and tells you they "love you but just need to have some sex… randomly? Spread my wings a bit?"

What, you think, is "spreading your wings?" We did shower sex? We did it up the butt??

If you're honest, you knew this first pillar of truth was coming. You knew sex was supposed to last longer than 45 seconds; you knew that Tiffany heart necklace he bought you for your 18 birthday was fucking tacky; you knew you were living a lie. Well done on spending the first year of college on a Megabus back to your hometown to see a boring cunt named Dan. Thank you, next.


Men Just Want to Fuck

Turns out your mom's not wrong about literally everything: Boys really are after one thing!

With that first breakup, you start to suspect that men are disgusting animals—pigs! rats! ratty pig-boys!—who see all women as pieces of meat and just want to endlessly have sex. Post-Dan, you're reading introductory feminism, which is confirming this miserable life lesson.

While your sexual encounters at this point can be boiled down to "two people with poorly-formed personalities rubbing bodies together," you're deep in a mode of believing that sex could lead to a potential relationship with every person you sleep with, even though you actively don't like most of them.

dating twenties

Age and Emotional Maturity Are Linked

There's been one common thread so far: young men. Like dough, every man in their early 20s needs to be left on the counter to rise. Don't even try to put him in the oven yet.

You know you should make efforts to date someone older.

Age and Emotional Maturity Are Not Linked

You decide to date an older man (he's, like, 26), who turns out to be a vile little princeling. Your big grown-up move ends in you being lumped with yet another guy being constantly passive aggressive and going silent in arguments, which is embarrassing. You decide to spend a lot of time thinking about a man's age before bothering to date him seriously in future. Biggest curveball yet.

A Partner Should Provide Financial Security

Riding a post-feminist wave, you either: I. get a legitimate pay-pig to see you through college and/or early employment; or II. meet someone who's incredibly grateful to be dating you, who observes you like a breeder does a show pony, and who chooses to express their affection by throwing money at you. You get off on the transactional nature of sex and love—an empowered woman getting what she wants!

'The One' Is Real

This is it. Everything about the meeting felt fated, an instant connection you've never had with anyone previously. There’s no point in having verbal conversations because the two of you operate on a cerebral plane. This is what Beyonce was singing about in "XO," each day feels a tiny bit like coming up on your first ever pill. They had your hair in a hand-held ponytail while you threw up, and went to the corner store to get toilet paper when you had the shits. They go down on you to completion and cook actual recipes off a phone when you come over. Friends comment that they’ve never seen you this happy. You don’t have to try. This person treats you like a human being, not like a girl or woman. Disney and your mom (again!) and heteronormative patriarchy were right! The one true love exists! That’s why everyone else feels terrible—they're not in true love, the sad-sacks!


'The One' Is Not Real

One or both of you fucks it up because—you realize—one or both of you didn't know yourself as well as you thought you did.

For the next year, you spend much of your free time in the corner of a pub, bitterly asking couples questions about how long they’ve been together, snorting smugly when it's under two years. Pathetic! Importantly, you realize that no relationship begins until the magic two-year mark—before that is the honeymoon period, which is a lie—and that there is no "one." Everyone older than you who stayed in their first real love relationship is made of less complex matter than you, doesn’t know themselves well enough, and hasn’t had the miserable life experience, so will definitely just reach middle-age and have an embarrassing period of…

Hoeing Is Real

…fucking everyone you can get your hands on. Yeah, obviously you once saw yourself settled down by this late stage in life, age 25, but why have another failed relationship when you can make everyone laugh at your stories (your life).

Expect cartoon bedspreads, pillows that smell of scalp, week-old discarded ready meal trays, and watching men play video games on a loop. You'll also see some huge dicks.

You learn: Threesomes are high drama but ultimately unsatisfying; that sex can be very good and very bad, and all the shades in between; and that although it is possible to like many "types" of person, you mostly just gravitate toward the same guys like a horny homing pigeon.


Men Don't Always Want to Fuck; in Fact, Do Straight Men Even Like Sex?

You realize dating is just turning up at a venue, having 3.5 pints of beer, and leaving thinking either, What is wrong with me? or, What is wrong with you? While you are desperately seeking sex, men are desperately seeking… a girlfriend? They also aren't the sexual aggressors you once believed them to be. Most men are just clueless puppies, bemused but pleased when you flirt with them. This goes against everything you were taught and have been conditioned to believe. You are the initiator of the actual sex, while men reply to your sexts with nonsensical emojis.

In fact, the more you mature, the more you see other people clearly. A few men have fantasies about you, project them onto you, and see whatever they want to see at that specific time. You recognize this and back away. Are you… beginning to know what you want?

Okay, Age and Emotional Maturity: Confirmed, Not Linked

You date a man in his mid-30s who calls his exes narcissists. He has a tantrum because you subtly emasculate him by ordering first at a bar or beating him in a neck-and-neck game of table football, and exits the room screaming about his mother.

relationships dating

Partners Should Provide Nothing But a Good Fuck and Make You Laugh

Is this you settling or becoming more realistic? Who knows! The better part of a decade has shown you that all you needed from a man all along was: The ability to go three times in a night and a consistent flow of quality memes.

Clarity/Namaste/Death Is Coming/Look at All That I've Learned

You find peace with dating. Facts: Romantic relationships really do require compromise, should never be transactional, you should always be present when you’re with someone (get off your phone for an evening, Jesus), and it's only going to work if you like the same kind of sex, I'm sorry. You see younger women giving inspirational dating advice online and feel ancient and content about that.

Maybe you meet someone else who makes you want to create another cult of two. Someone you look at while they engage with other people and think, Yep, I’d crawl across broken glass for that shithead. Maybe you have a second "the one is not real" meltdown six months down the line.

Either way, it is now that you realize you—and everyone else—ultimately knows very little about dating. That includes knowing what you want. But you are clear about what you don’t want. You leave situations that aren’t right quicker and with more belief that everything will be OK. You develop something resembling personal boundaries. If you’re very lucky, you won't date someone with single raw pillows ever again.

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