15 Guys You Will Date In Your 20s

Generally, your 20s will be filled with many jobs, many apartments, many friends, many hangovers and many men. In most cases, many, many men. Sure, some lucky women find the person they are going to spend the rest of their life with at the age of sixteen. That’s great for them and all but, for most of us, our 20s are spent dating men, most of whom we will not be spending the rest of our lives with. That’s okay. That’s great, even. You will learn a lot about yourself as a person by inviting these different guys into your life for however long they are in your life.

The thing about the guys you date in your 20s is that they are usually wildly different. Since you are at a state in your life during which you're still learning who you are, you're still in the process of learning who exactly you want to be with. This is something that can only be learned from trial and error, so you may have to date many wrong guys before you find the right guys for you to date.

Regardless of who you are, there are usually a few men that all women end up dating in their twenties. We've rounded up fifteen guys that you're going to end up dating in your twenties, no matter who you are. They may break your heart, they may help you know who you are as a person, they may love you tremendously - whatever the case, they will be in your life.

15 The Guy Who Breaks Your Heart

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This is just how it is. In your 20s, you will have your heart broken. No, you will have your heart shattered. It is probably the best time to endure such a break up though, because most of your besties will still be single and ready to buy you shots and help you get over the a$$hole who broke your heart. If you wait until 30 or 40 for your first Earth-stopping heartbreak, it will be harder because your girlfriends will most likely be married or engaged or pregnant. They’ll have less time to devote to your heartbreak than they would in their 20s.

This guy comes in all shapes and forms. It may be a long-term relationship that ends. It may be a cheater. It may be someone who ghosts you after promising you the world. Whatever happens, he’ll be the guy who deeply hurt you. While this hurt doesn't last forever, it certainly changes you as a person.

14 The Guys Who Know Everyone 

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You may not be sure if you like him or all the access he provides but that’s okay. He’s the guy who somehow knows everyone from everywhere. When you’re with him, there are free drinks and you never wait in line. He somehow has backstage passes. He’s invited to openings and private parties. His whole life seems glamorous and exciting just because he knows so many people.

While dating him, you’re life, too, will seem a bit more magical than usual, but, in the end, these guys are usually more exciting for their hook ups rather than their actual personalities. While it will be a time in your life that you look back on fondly for all the fun you had, you're probably more into the fun you're having with this guy rather than the actual guy.

13 The Guy With Bad Timing

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So, you many not actually date this guy. When he was single, you were in a relationship. When you were single, he was in a relationship. When you were both single, he decided to move to Boston for school. When he got back from Boston, you left for a job in LA. This is the guy with bad timing.

You and him will have wonderful chemistry. You’ll both clearly be attracted to each other but there will never be a good time for the both of you to hook up. If you do manage to hook up, it will probably be followed by something else ruining the opportunity for you two to actually date.

In the end, you’ll move on from your twenties and probably wonder what would have happened if you two could ever just get the timing down.

12 The Guy Who Is Way Too Nice

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Ugh, why is this guy so nice? Even when you’re mean to him, he’s still nice to you. You wish that he’d show some other emotion but, even when you’re thirty minutes late for a date because you couldn’t pick out an outfit, he’s still just nice to you.

It could be his natural demeanor or he very well could just like you so much that he’s always nice. At the end of the day, though, you really wish he’d just stop being so damn nice all the time. This will all be very annoying to you while you're dating him but a few years later, you’ll look back and think, ‘He was so nice. Why didn’t things work out with him?’

11 The Bad Boy

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The bad boy is the opposite of the guy who is way too nice. Well, actually he can be very nice too, but the thing is that he’s bad in some way shape or form. He may be the kind of guy that blows you off or ghosts you. He may be the kind of guy who parties too hard. He’s one of those live fast, die young guys. Whatever it is that makes him bad, it is also part of his appeal.

The attraction to him is that you want to tame him, or perhaps you want to prove you’re just as wild. Whatever it is, the fact that he’s a bad boy is a draw. Of course, looking back on dating this guy usually results in you thinking, ‘What the heck was I thinking?’

10 The Seemingly Perfect Guy

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The seemingly perfect guy is, well, seemingly perfect. He is good on paper, the type of guy who seems to have his life together. You’ll often look at him and wonder how he has everything so together and you often feel like your whole life is falling apart. He has a good job, his finances in order, a cool apartment or maybe even a house.

The seemingly perfect guy is attractive for these reasons. You imagine marrying him, but the only issue is that you probably don’t want to marry him any time soon. Why couldn’t you have met him in, like, 5 years? Well, that’s just the way the world works.

When you break up, he’ll probably start dating the girl he’ll marry because that dude was ready to settle down. Whatever, at least, you’re still free to go to happy hour and stuff.

9 The Co-Worker

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This may be a full on dating situation or you may just be dating him in your head but there is definitely a co-worker with whom you’ll have a relationship or like to have a relationship.

The thing that makes it so easy to like this guy is that you have so much in common! You can talk about work stuff, career goals and that guy Todd from accounting who is always eating tuna fish sandwiches and stinking up the whole office. The unfortunate part is that, well, you work together so if things end badly, it makes for an awkward workplace.

For the most part, this relationship usually ends with you learning that you shouldn’t date anyone you work with, no matter how cute Jim and Pam made it seem on The Office.

8  The Guy You Never Actually Know If You’re Dating

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He doesn’t like labels. He just wants to see where it goes. He just got out of a bad relationship and doesn’t want to use the titles boyfriend/girlfriend just yet. Whatever the case may be, you’ll never really know if you’re dating this guy.

It will never be Facebook official but you’ll binge-watch Netflix together and go on dinner dates. He may introduce you to his friends as a girlfriend one night and then a friend another night. The whole situation is infuriating. You’d just like a straight answer! Are you or aren’t you two dating? It’s all so confusing.

Eventually, you’ll break up but it won’t really be a break up because you two were never really dating.

7 The Guy Who Is Way Too Into You

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Gross. Why is this dude so into you? He seems like a creepy stalker but, in reality, he just likes you a lot.

For some reason, the amount of attention this guy gives you just creeps you out. If he calls you beautiful one more time you may barf. The fact that there is no chase makes him just utterly unattractive to you. You wish he’d pull away just a little bit but he never does and, unfortunately, having him at your beck and call makes him so unattractive.

Hopefully, he’ll get the hint or you may end up having to tell him to leave you alone, in which case, he'll text you three months later, 'just to see how you're doing' and you'll hate that too.

6 The Guy You Are Way More Into Than He Is To You

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Ah, now the tables have turned. You will certainly date a guy who you will be way more into than he is to you. You like him a lot. You can’t help it. Unfortunately, even though you’re really trying to get him to like you just as much, nothing you do seems to work.

You think everything about him is so interesting and cool. Every time he tells you about a new show, band or movie, you check it out right away. But, why doesn't he text you back? Why are you always the one initiating all of the texts? Wait, are you being clingy?

It dawns on you and it is an awful realization. You are so much more into him. It hurts to realize it but after the sting wears off, it's a great lesson in figuring out who is actually into you.

5 The Player


Beware of the player. He will break your heart in some way. If you get into an actual relationship, he may cheat on you – emotionally or physically. If you never end up in an actual relationship, you will probably still be emotionally hurt in the end.

The thing with players is that they are just oh so charming. Generally, in your 20s, you won't be experienced enough to sniff out the bs lies that a player feeds you, which will result in you falling hard and fast for this guy. Fortunately, after dating one player, you're usually able to detect others from that point forward, so this guy makes for a great learning experience.

In the end, he’s just the type of guy who needs a lot of attention from women, which is a sign of insecurity, despite how secure he may seem.

4 The Guy Who Is Rebounding

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In our fast-paced society, who has time to really sit down and get over one ex before jumping into a new relationship? No one. It seems like as soon as we change out Facebook status back to single, we are swiping through Tinder as quickly as possible.

Because of this, you will likely end up in a relationship with someone who is rebounding off their ex, mean, yes, you are the rebound. Being a rebound is a tricky game, especially if he freely talks about his ex in front of you. Is he over her? Is he not over her? Should you say something? It's a minefield.

This relationships usually fizzles out as the guy is probably using you as a Band-Aid to help him heal his wounds from his last relationship before actually getting back out there and being single.

3 The 30 Something

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You probably met him in a bar. He was wearing a suit and quite obviously a bit more well behaved than the younger guys, who were all getting way too drunk during happy hour.

He makes you feel so young and inexperienced. You love hearing stories about his career, because he has a 'career' and not just a 'job'. You love going to his apartment and seeing all the little adult-things just lying around. He has fruit bowls with actual fresh fruit in them. Something about all of this makes you feel a little inadequate, but he also seems to like you for your youthfulness. When you say you haven't heard of something, he jokes that it was before your time.

Of course, these relationships usually end because either the 30-something guy is pretending he's younger, or you're pretending you're older. In the end, he'll go back to dating 30-something year old women and you'll go back to those younger guys all getting too drunk during happy hour.

2  The Guy Who Gets Away

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Here's the thing about your 20s: even the best guys can sometimes get away. Our 20s are a time in which a lot of things happen. You may lose your job, get a promotion, move to a new state, change your career all together. Sometimes, this causes you to thrive, working out all the time and waking up early. Other times, you may be binge-watching TV for days on end while drinking wine straight from the bottle. The point is that in your twenties, sometimes you're a goddess and sometimes you're, err, not as goddess-like.

Unfortunately, since a lot happens during these ten years, you sometimes let people fall out of your life for whatever reason. This may not break your heart and you may not even realize it at the time but looking back, you may wonder what happened to that guy who was perfect for you. Well, you were in your 20s and sometimes even a guy who is perfect for you can't make it work with you at that point in your life.

1 The Love Of Your Life

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You might not spend the rest of your life with him, and that’s okay. In your 20s there is such a sense of hope, possibility and optimism that it is easy to fall in love with someone in a way that may be impossible as you get older. The older you are the more you see things ending and falling apart. It is harder to let yourself love someone so completely as you get older and wiser. That is why you will probably love a guy in your twenties in a way you will never feel the rest of your live. It is fierce and powerful, and something you may not want to feel again because it makes you very, very vulnerable.

You may not marry him, but you will certainly love someone in your 20s in a way that never happens again. If you're lucky though, maybe you will marry this guy. Whatever happens just don't marry The Bad Boy, The Player Or The Guy Who Is Rebounding. Actually, if you're going to marry any of the guys you date in your 20s, it should only be this guy.

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