The Men We Dated In Our 20s (And What We Learned)

Alexa Weeks | 22.11.17 | | Comments

If I had to guess, I’d say that Prince Charming is certainly in his mid 30’s. But for some reason, we’ve always believed that we would find him in his 20’s. A fixer-upper that we could discover before he bloomed, clean him up, and make him see that we were the princess he’s been looking for all along and we’d be in a beautiful and loving relationship! Well…can’t blame us for trying.

After an entire decade of throwing ourselves at boys who weren’t interested, falling into a drawn-out relationships with guys we’d just end up friend-zoning, and being the side-piece to the “man of our dreams”, we can definitively say that dating in our 20’s is no walk in the park.

It should make you feel better to know that you’re not alone. Us girls in our 20’s, for one reason or another, have a habit of picking the same 5 types of guys to turn our lives into a real-life episode of 90210. Looking for love seems to be same globally. These are the guys we tend to meet when we’re in our 20’s in real life and not through online dating sites (Which are so popular these days!).

1. The bartender

Once you turn 21, it’s bar-o’clock 8 days a week. You and your girlfriends get into a routine of frequenting the same 3 or 4 bars and inevitably you end up developing a crush on the bartender. I mean…he remembers exactly how you like your gin & tonic – with 2 limes instead of 1. It must be love, right?! You feel it, he feels it, it’s definitely a match.

Then one night, it happens! You manage to drag him aside during his break for a moment that you remember to be utterly romantic, but it was probably just one big mess. You text him the next day, and he eventually gets back to you 3 days later. It’s official. This must mean that you’re in a full-blown relationship. Or so you think…because you’re 21. You know how this ends: a few love confessions after turning up at his bar (because how else are you going to see your new boyfriend?) mixed with some crying and “you don’t deserve me” declarations. Now you and your girlfriends have to avoid that bar because “your ex works there”. Good work, sister.

2. The guy who isn’t ready to settle down

Now you’re 23 and “so over the bar scene”. You just want to find a nice guy with whom to settle down and adopt a pug. You start dating the computer science major that lives next door. He’s total husband material: he’s smart, has got a great career path, opts for paper instead of plastic, and you two would have the cutest babies.

You date for a solid 12 and things are good. Great, actually. So you start dropping hints about taking things to the next level, about where you’d like to get married and how many kids you want to have. You begin to realize that your boyfriend is not picking up what you’re putting down, so you go for the straightforward approach and just tell him that you’d like to get married someday.

To your utter shock and dismay, he starts pulling back and eventually tells you that “he’s not ready for a serious relationship”. Why? Because he’s goddamn 23 years old and you are, too. Wake up!

3. The one who’s married… to his job

You’re 25 and have just found the recent college-grad of your dreams. He’s also 25, comes from a great family, flosses everyday, and has just signed on with a prominent investment banking firm. This firm is going to pay for him to get his Master’s degree and then offer him a 4-year contract when he’s through with an incredible salary and benefits. He’s all set. You’re all set.

Because you two are in love, it’s easy to picture the future. You’ll stick by his side as he studies and make him dinner every night when he comes home from the library. When he starts his job, things will be easier. You’ll brunch with his family on the weekends because you’re really close with his sister, and you two can finally afford the occasional vacation to Mexico.

But things don’t go as planned. Most of his 2-years studying for his Masters is spent at the library and you often eat dinner alone. You hold on to hope that it will get easier. Once he’s graduated, however, he starts putting in 12-hour days at the office, and has to schmooze with clients after work. You barely see him and it takes a toll on your relationship. It breaks your heart but you’ve got to be honest with yourself: this isn’t going to work. Not now. He’s the one that got away.

4. The safe bet

At 27, you’ve had it with guys who waste your time and break your heart. You’ve been choosing all wrong. So, when the super-nice guy from work asks you out – you go for it. He’s not necessarily your type but you decide to give it a try. This guy is soft-spoken, considerate, and has great hygiene. Your mom would love him.

He treats you right, holds the door open for you, and sends your flowers “just because”. He is so ready for a relationship and would put a ring on it tomorrow! But there’s something about the way he kisses you that feels…weird. Not to mention that every time he holds your hand, it feels like your holding hands with your grandfather.

On top of all that, he’s so levelheaded and reasonable that every nice thing he says starts to get under your skin. Just once you want to see him get irrationally jealous! You start picking fights with him just to get a reaction, but when he remains cool, calm, and collected for the 35th time, you’re fed up. Nice boy, bye.

5. The younger guy

At 29, you have an epiphany! You’ve been picking all the wrong guys for almost an entire decade. You’ve figured out what kind of man you want to be with. Keyword: older.

You start looking for that salt and pepper Harrison Ford-esque man- even changing your Tinder settings to men aged 35 and up. These are the guys who will wine and dine you because they’re established, call you on the phone because they’re a bit more old school, and wife you up because you are a sexy, wise woman who is finally in the right stage in her life to settle down.

Then you meet Chad, the 23-year-old aspiring DJ who still lives with his college roommate and takes his dirty clothes home every weekend for his mom to do his laundry. Sure, he plays Xbox live for hours on end and hasn’t yet got his big break in the entertainment industry but there’s just something about him. You tell yourself that “he’s really mature for his age” and start sleeping over at his place more often than you should.

You get addicted to this guy. He’s so hot, so charming, and has big dreams that could possibly, maybe, probably be reached. Before you know it, you’re back in the bar scene with his 23 year old friends, taking shots of tequila instead of wine, and somehow giving his mom a break by doing his laundry on the weekends. When will we learn? Maybe next year.

While you may consider every man (or boy) that you dated in your 20’s to be a big, fat mistake – they’re not. Think of them as training wheels; you weren’t ready to go fast, anyways. Your 20’s are for learning about who you like, how you love, and what doesn’t work for you. For the girl entering into her 20’s with nothing to lose, take note from the women who have walked before you and maybe you can avoid stepping in some potholes along the way. For the 25 year old who has been let down but is still optimistic- remember that self-esteem and self-respect will serve as good-guy magnets in the years to come. And finally, to the 29 year old who’s finally reaching her kick ass, independent, least messy stage yet…embrace your 30’s as they come- that’s where all the husband-potential is anyways.

Alexa Weeks

Alexa is a writer, traveler, and self-proclaimed online dating expert from Seattle. From making mistakes, to falling in love, she’s experienced it all. Alexa is here to give you all the tips, insight, and advice you'll ever need in the world of dating and romance.

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