Your 20s are filled with pros and cons. Pro: Independence. Con: Bills. Pro: Eat whatever you want. Con: Slowing metabolism. Pro: Date everyone! Con: People are jerks. However, your 20s are also filled with valuable lessons, like maybe three-day-old pizza isn’t a well-balanced breakfast or maybe you shouldn’t give that d-bag your attention once he finally texts you back a “hey” after three days of radio silence. Your 20s are a time to make mistakes, figure out what you want, and who you want to surround yourself with. They’re hilarious, messy, heartbreaking, and important.
There are more than a few losers on this list, because we don’t always make the best decisions, but there are some gems, too. Absent from this list of 20 boyfriends you’ll date in your 20s? The One. There’s no set time or decade in which you’ll meet the love of your life; maybe you’ll be in your 30s or 40s, maybe you’ve already met him (if so, lucky you!). Use the time you have to learn to be happy with yourself, before feeling like you need someone else. Usually, the time you spend going through the duds might be the exact right moment when you fall head over heels.
20 The Professional
He has his whole life together and you’re still losing your cellphone and driver’s license on Friday nights. He has a great job and a savings account while you’re eating an entire box of Kraft Dinner and spending your afternoons binge-watching TV series on Netflix.
The Professional is the aspirational boyfriend, the guy you can really see yourself having a future with – once you’re ready to begin your future. He’s educated, respectful, and caring. He understands health insurance and is always impeccably dressed for any occasion. But, you’re still in your (probably early-ish) twenties and figuring out what exactly it is you want – out of life and out of relationships – and unfortunately The Professional already knows what he wants in both areas. At least he gave you a taste of what a real man can be, and once you earn your own Boss Lady status, you might find that The Professional is more boring and less alluring than he first seemed.
19 The BFF
You love the same TV shows, laugh at the same parts in movies, and would rather do nothing all day than do something like go on an actual date. The BFF is a best friend who also happens to be your boyfriend, but you’ve been spending so much time being buddies that it’s taken you a while to realize there’s no real spark left in your relationship.
When you inevitably break up with The BFF, you’ll have one of those few opportunities to make a friend out of an ex, because that’s basically who you both were all along, except you got naked together a few times. The BFF shows you an important part of all future relationships, which is easy conversation, laughter, and total comfort. You might not be sexually attracted to him anymore (and were you really ever?), but you can’t deny that you and The BFF had some fun times together.
18 The Weekend Hook-Up
Like happy hour margaritas and 3am double-cheese pizza orders, The Weekend Hook-Up just sort of became a Friday and Saturday night habit before you were fully aware of it. This boyfriend is the guy you drunkenly sleep with so often that you’ve become accustomed to seeing yourself leave his place Sunday morning with smeared eyeliner and unwashed hair, the picture-perfect vision of the morning after.
You’re probably more than a little embarrassed by your actions, because if you’re being honest with yourself, you’d never willingly see this guy outside of the wee hours of the morning, let alone introduce him to your family and friends. The Weekend Hook-Up is just attractive enough to convince yourself that your late night activities are worth it, but you’re usually so sloppy when it happens you can’t be totally sure. Hey, at the very least you have a fun go-to story to tell all your friends when you’re sipping on morning mimosas or mochas at Sunday brunch!
17 The Undefined
Are you dating this guy or aren’t you? You see each other every couple of days, but you’ve never met his friends or family. You sleep together but he absolutely refuses any PDA. You text every hour of the day but you definitely don’t have any pictures together. The Undefined boyfriend can be one of the most soul-crushing of relationships you’ll have, because he gives you the impression that you’re not someone to be proud of. He’ll feed you some line about not wanting to label things, but that’s complete BS because your guy should want to show you off! Unfortunately, your 20s are a time of insecurity as well as self discovery, and so you’ll find yourself coming back to him again and again because he’s familiar, even if you don’t know where you stand. Once he (inevitably) ends things with you out of nowhere, you’ll eventually be forced to realize that while he took up prime real estate in your heart, you weren’t nearly as important to him, and you don’t have time for that!
16 The Coworker
You bonded over your a**hole boss or your mutual hatred of spreadsheets, and now The Coworker has moved from being your office buddy to your bed buddy. It’s an easy trap to fall into, because you have the same schedule and already have a common point of interest.
In your 20s, you’re almost guaranteed to jump from job to job for a bit, so hooking up with a coworker isn’t necessarily as bad an idea as it may have been when people settled into jobs for the long haul. But, like spending too much time with anyone might do, you can easily get sick of The Coworker, or realize that outside of work (and bed) you don’t have all that much to talk about. So, take this relationship with a grain of salt and have some fun. If you end up being the Jim and Pam of your own office, awesome! If not, no big deal, just make sure you’re not compromising on your career for the sake of a (potential) fling.
15 The Man-Child
Oh, man, is this guy a baby! The kind of guy who throws a temper tantrum if you beat him in a board game or refuses to trash some painfully unfunny and downright offensive T-shirt because he’s had it forever (even though it was a joke gift). The Man-Child makes bad jokes and no one in your circle ever really liked him, but you stuck with him anyway, mostly because he started whining any time you made a move to end it.
The Man-Child refuses to grow up, and he’d rather spend his nights playing video games with his friends than enjoy a romantic evening with you. He’s pretty thoughtless – because he’s selfish – and has always gotten his own way, and that’s not about to stop since you came along. He’s only ever had to look out for himself, so don’t waste your time expecting him to give you the attention and admiration you deserve.
14 The Fixer-Upper
He has a troubled past, a rocky family life, and has probably jumped majors, jobs, or careers more than a few times. He’s a bit standoffish and regularly starts an argument with you over the tiniest things, but you chalk it all up to his wounded, sensitive soul. The Fixer-Upper requires a lot of help, attention, and love, but it’s pretty doubtful you’ll ever see any of it in return. Your relationship is so up and down and all over the place that your friends can’t keep up anymore. However, you – sweet, nurturing soul that you are – stick with him, because you think you can be the one to tame the wild beast or finally get him to open up to you and share his pain. Eventually, you’ll realize that The Fixer-Upper only takes, takes, takes, and that you are too good to be emotionally manipulated into giving all of yourself away for nothing.
13 The Clinger
He likes all your Instagram photos, screenshots your Snaps, posts messages of adoration on your Facebook, and blows up your phone with heart-eye emojis. All that attention was sweet and flattering at first, but now it’s beginning to feel suffocating. The Clinger wants everyone to know you two are together and just so in love!
His constant need to check up on you and your relationship is an obvious sign of his insecurity, and while he thinks you appreciate him tagging along everywhere you go, it’s really made him into an unwelcome guest at every occasion. He talks about your future like it’s a definite, which makes The Clinger is a hard one to break up with. He’ll beg you to reconsider and insist you’re making the wrong decision since he’s treated you so well, but in reality he’s dragging you down and you’re a girl who needs to soar.
12 The Artist
Maybe he’s a writer or a poet, a musician or an actor, a graphic designer or a cartoonist, but you know that this guy is all about his art. He alternately takes caffeine and alcohol in IV form, and considers the perfect date night to be you watching him as he jams out with his band. It seemed cool and sexy at first, like you were living out some high school fantasy, but now all he wants to talk about is his music or his art or the power of words and you’re getting a little tired of it. That, and the fact that he can’t afford food and shares his messy one-bedroom apartment with three other dudes so privacy is pretty much nonexistent.
You’re all for him following his dreams and would never want to stand in the way, but you know that with The Artist, his work will always come first and you will always come second. But hey, if you’re lucky, maybe you’ll get an awesome power ballad to commemorate your love.
11 The Older Man
This guy is the one who will show you the world – or at least everything that you were missing out on when you were wasting your time with all those boys. The Older Man has obviously been around a bit and can definitely show you more than a few things in the bedroom department. You admire his ambition and seasoned outlook on life, and he eliminates a lot of the game playing you had to deal with in previous relationships – plus there’s something undeniably sexy in your May-December taboo.
Hopefully The Older Man is unattached, otherwise you’re setting yourself up for the heartache and unfair deceit that comes with being the other woman. While The Older Man is a great break from the guys you dated in college (or even after), he’s rarely your forever love, because you’re both at different points in your life, and while he might be slowing things down, you’re just revving up.
10 The Jerk
Why are you even with this guy? Your friends hate him, your family hates him – even you don’t like him very much! The Jerk takes his d-bag worthy moves from pick-up artists or similar, and uses negging and ghosting as his primary tactics to keep you on the line. He openly flirts with other women, insists he’s smarter than you, and gets belligerently drunk every weekend. You and The Jerk are on-and-off so often, no one knows where your relationship is at. But don’t even think about trying to move on, because, like a sixth sense, The Jerk knows your plan and swoops in to steal you back. He’s cocky and sexy, and you kind of hate yourself every time you give into him, but The Jerk is one of those boyfriends every girl has in her 20s. The best you can get out of your time with him is a valuable lesson on how you deserve to be treated – and the knowledge that everyone around you was right about him all along.
9 The College Leftover
Your flip-cup and beer pong days may be over, but this guy is somehow still kicking around. The College Leftover spent so much time crashing on your college futon that you forgot he never really left. You’ve been through each other’s growing pains and he’s seen you during your messiest, earliest, drunkest days, so you don’t know if it’s love or familiarity that’s keeping you both together.
However, like cereal eaten for all meals and puke in your hair, some things are better left in college. Once you graduated your mutual home, you realized you both didn’t have that much in common beyond dorm proximity. Because you’ve spent some of your prime dating years with this guy, you may not be able to imagine life without The College Leftover by your side at all hours, but trust me – you don’t miss early classes and weekends spent hungover, and pretty soon you won’t miss him either.
8 The Backup
Let’s be honest here: neither of you were each other’s first choice. He’s still not over his ex, and neither are you, but you needed a plus-one to some event and he’s not totally terrible. In-between sips of Chardonnay, he’ll bore you to death with stories about his ex-girlfriend, and how if only he hadn’t done that one thing, they’d still be together, and how every song reminds him of her, and she was the greatest thing to ever happen to him, etc. etc.
Your relationship with The Backup is obviously a sham, and you’re both only in it to make your exes jealous. It’s not healthy for anyone involved, and instead of supporting one another through this tough time, you’re feeding off your mutual misery. For your safety and sanity, toss this one out because while a rebound can be useful in times of need, neither of your hearts are in this fake one.
7 The Hopeless Romantic
Are you in the mood for roses, love letters, a boombox held over the head by the guy who wants to sweep you off your feet? Then The Hopeless Romantic is the perfect guy for you! He’s sweet and caring, and he remembers tiny moments that you’ve long forgotten about, because he just thinks the world of you. It’d be adorable and thoughtful if it weren’t so … much. To be honest, The Hopeless Romantic can be overwhelming with his talk of “together forever” and his poems celebrating your beauty. You want romance, but he’s taking it a step further into obsession territory. The Hopeless Romantic isn’t just a softie by nature – he genuinely believes this is what women want. And he’s right – to a point. It’s just that instead of giving you a taste here and there, to keep up the chemistry, he’s insisting on force-feeding you the entire romance buffet.
6 The Forbidden Fruit
You know you shouldn’t be with this guy. Logically, you know you should stay away, and yet here you are, waiting for a text or waiting on his doorstep. Maybe he’s a higher-up at your job, a best friend’s ex, or another friend’s brother. You’ve been warned to keep your hands off him, but with someone that cute, how could you resist?
Part of you gets off on the idea of your relationship being taboo – if anyone found out, you could kiss your professional career or friendship goodbye! The sneaking around is almost more exciting than actually spending time with The Forbidden Fruit, which is why it’s bound to fizzle. Eventually you’ll miss the real relationship bonuses like spending time together in public or sleeping over at each other's houses. Keeping the whole thing quiet can get exhausting as you twist yourself into emotional knots. Being each other’s dirty little secret is hot for a while, but everything cools off eventually.
5 The Mama’s Boy
He started as a sweetie, he really did! That’s what you tell your girlfriends when they give you a hard time again over his maternally-imposed curfew. Always at her beck and call, his mom is the number one woman in his life, and don’t think that’s about the change since you two got together.
You loved the sensitivity and thoughtfulness of The Mama’s Boy, but as you’re growing into your independence and maturity, he seems content to let his mom keep control of his life. You can’t make a date or buy him a gift without checking if it’s okay with Mom first, and she’s always subtly undermining or insulting you just enough to ensure that her boy stays a mama’s boy forever. That twin bed at his parent’s place is starting to feel a little bit too small, and your relationship just can’t handle all three of you – get out now!
4 The Big O
This guy is sex on legs. He’s easily the best you’ve ever had and there is never a moment you’ve left each other’s company without your hair in tangles and your clothes hastily buttoned up. You’ve really never spent any time outside the bedroom and that suits you just fine, because The Big O gives you plenty of O’s while you’re there!
With fiery passion like this, though, you know it’s probably not meant to last. Conversation is basically a no-go, since you’re mouths are always on each other, and while he’s seen you naked more than anyone else, you couldn’t tell anyone his last name or favourite colour. The Big O will give you a few months of bliss and then stop returning your calls. Don’t take it personally – the best you’ve ever had is not usually long-term material. Take your happiness and use it as a yardstick for future lovers (not literally).
3 The Tinderer
So you met him on Tinder (or Bumble or OkCupid or whatever) and once you met up and saw that he looked nothing like his picture, you stuck around instead of running. Out of desperation or perhaps genuine connection, you’re still kicking it with The Tinderer, even though your friends are always in disbelief whenever you tell them you’re both together.
The 21st-century equivalent of a blind date or set-up, The Tinderer is the result of your spontaneity at its worst. In text he’s way funnier, charming, and sexy than he’ll ever be in person, so you keep things going out of boredom and the fact that he uses the perfect amount of emojis per text. The Tinderer lets you fulfill your meet-cute, romantic-comedy dreams because of how you met, but if you’re being honest with yourself, he’s more of an excuse to have a partner-in-crime while drinking (whom you maybe occasionally bone).
2 The Girlfriend
Hey, your 20s are for experimentation, right? While not technically a boyfriend, The Girlfriend can be a valuable addition to your dating arsenal, and even a necessary step towards finding yourself.
The Girlfriend just sort of happened. Maybe she began as a friend of a friend, or maybe you met her at random. Maybe you were drunk or maybe you weren’t. The point is, The Girlfriend is someone you don’t have to hide from. All those gross girl-things you kept from the guys you dated? No big deal here, because she’s a girl, too! You might think of it as a fling, and maybe you’ll never really identify The Girlfriend for what she is until you two are long over. From spending all your time together, to swapping clothes and kisses, The Girlfriend can help put you back in touch with who you are. Don’t use her and lose her, however – if you don’t identify the way she does, you need to give her a heads up before anyone gets really hurt.
1 The Fan Favourite
Your parents love him, your best friends love him, even your cat loves him! The Fan Favourite is always invited to every holiday dinner and party, is in close touch with your family, and can charm any new person you introduce him to. He’s a great guy, so why are you not feeling the spark? The Fan Favourite may have been the result of a set-up, which is why your friends are gunning for you guys to stay together, and why you can’t bring yourself to let him go. There’s nothing actually wrong with him, which makes you think you’re crazy for wanting to give up such a good thing.
The important thing to remember when you’re dating The Fan Favourite is that it’s YOU who’s dating him, not everyone else. You can’t make everyone happy, so just follow your heart and maybe you’ll get a great friend or wingman out of it!