20 Things No One Ever Tells You About Dating In Your 20s

I guess “ladies” aren’t supposed to talk about their age, but I’ll just admit it: I’m in my 20s and I don’t care if you know (seriously, who cares?). Anyway, considering I’m in my 20s, I am experienced in the art form that is dating in your 20s. Although I’ve been in a serious relationship for the last five years (this is where I date myself), I did go through close to four long, hard years of dating as a 20-something. I know for a fact that there are some things no one ever tells you about dating in your 20s, and you deserve to know those things.

Maybe some of you reading this are in high school or college or in your early 20s, and you want to know what to expect. Maybe you’ve heard some things: guys are supposed to be more mature and ready to commit! The dating world is quite similar to movies and TV shows where you literally cannot go anywhere without finding a hot person to hook up with. Friends with benefits often turns into full-fledged loving relationships. If you’re single for too long, you have to buy a cat. Tinder is essential. You will meet someone at a bar or a club. Dates often include going back to someone’s fabulous house/apartment where they live alone and you can sleep there and then wake up wearing their button-down shirt looking really adorable for someone who just had a one-night stand and then you can go home and gossip about it at brunch with your friends.

In general, almost none of this is true. Except for the gossiping at brunch with your friends part. That is quite a nice perk to being in your 20s.

I say I had “long, hard” years of dating in my 20s, because dating in your 20s is hard. It’s also an exciting learning experience that will leave you with a lot of stories to tell in the future. That’s not to say it can’t be heartbreaking, because it usually is. But I wouldn’t trade my single years for anything. If you want to be prepared for what’s to come, you should keep reading. I’ll be real with you guys – here are 20 things no one ever tells you about in your 20s. It’s not always fun and everyone’s experience is different, but… you can expect most of these things to happen. Good luck out there!


1. The book He’s Just Not That Into You is SO RIGHT.


If you haven’t read the book He’s Just Not That Into You, read it, even if you’ve seen the movie. I read this book when I was 19 or 20, and it changed everything. The basic premise is that if a dude likes you, he will try for you. If he doesn’t call you back, it’s because he doesn’t want to. If he blows off plans, it’s because he doesn’t want to see you. If he won’t make you his girlfriend, it’s because he’ll never make you his girlfriend because he doesn’t like you enough. It’s harsh, but you have to be exposed to these harsh truths when you’re in your 20s. It’s hard out there!


2. Only some dudes get more mature as they get older. Only some.

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Growing up, I was stoked about dating in my 20s because I thought that guys in their 20s would be so mature. This…. is not true. Is it possible for guys to regress in age as they get older? Because it feels more like that. Many dudes in their 20s end up getting so freaked out by the pressure of commitment that they start to act immature and treat girls terribly. It’s kind of scary, actually.


3. Online dating is not easy in any way.


Tinder, Match.com, OkCupid, Coffee Meets Bagel… whatever your choice is, know that online dating is hard. That’s not to say it doesn’t work – it does! I know a lot of people who are in relationships thanks to online dating – but it takes patience and time. I tried online dating very briefly, and it was horrifying. I met awful dudes and do not have one positive story from the experience (some amusing stories, though). I know people who have stuck with it and ended up meeting awesome people they love now. So, definitely try it! But know that it will take you longer than a week to find your soulmate.


4. Your friends will become boring once they’re in a serious relationship.

such a good friend

As you and your friends get older, serious relationships become more serious. You don’t just talk about getting married – people actually go out and get freakin’ married. As your friends enter very serious relationships, they will start to slowly fade out of your life. You’ll watch party animal friends become homebodies who love being with their bae. You’ll watch the friend who was once always there become the friend who has to pencil you in a month from now. It’s tough, but keeping up friendships is work – and it’s sometimes worth it, but still.


5. Going to events without a date is tough.

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True story: I once didn’t go to my friend’s wedding because I didn’t have anyone to bring as a plus one. Every other friend I knew was going with a date except for me. I couldn’t bear the thought of being the only single sitting at a table full of couples, and so… I didn’t go. Rude? Yes. But guys, going to events without a plus one is low-key hard in your 20s. It’s certainly not the end of the world, and I don’t think I would ever pull that stunt again, but it’s definitely lonely. You get invited to a lot of things like that in your 20s – weddings, engagement parties, family stuff, etc. – and if you’re single, you dread having to find someone to bring along with you. You might want to react like Nick Carraway and get drunk (and you legally can), but that’s probably a terrible idea.


6. The fear of commitment is real.

commitment fear

I know a lot of people who say that saying you’re scared of commitment is just an excuse for “I don’t like you enough to commit to you.” In many cases, this is true. But there genuinely are people out there who are scared of commitment, and getting through to them can be very hard. In your 20s, this fear is real. A lot of people have it. It’s not easy to deal with. And sometimes it really is just an excuse.


7. People will ask you about marriage too often.

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Okay, so, once you’ve been done with college for about a year or so, you’re going to hear the same question over and over: “What do you think about marriage? Don’t you want to get married?” Everyone talks about marriage in your 20s. If you’re single, you hear the pressure to meet someone so you can settle down. If you’re in a relationship, everyone wants to know when it’s going to happen. If you’re casually dating someone, they ask, “Can you see yourself marrying this person?” IT IS SO STRESSFUL.


8. Being single is often something you won’t appreciate until you aren’t single anymore. 


Looking back on my single years in my 20s, I am so glad they happened. I learned so much, I had the most fun ever, and I really bonded with my friends. But when I was single? I didn’t feel that way. I spent a lot of time pining for a relationship. I cried about being lonely all the time. I felt hopeless and sad and alone. I thought everything would be better if I met someone. It’s jut something you don’t appreciate until you aren’t single anymore, which is annoying.


9. Staying in a relationship that doesn’t have a future isn’t a great idea.

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I don’t necessarily agree with the idea that every single relationship has to have the end goal of getting married. At the same time, I also don’t think there is much of a point in being with someone if there is no chance of anything happening between you too – if marriage is something you want one day. If you’re starting to really fall for someone, but you know nothing will ever happen, you should get out before the heartbreak is too much to handle. Trust me.


10. Putting your relationship on social media is very overrated.

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Before your 20s, you love talking about bae on social media. Pictures, sickingenly sweet statuses, #relationshipgoals all over the place. But as you get older, you realize it’s totally overrated. First of all, no one needs to know your business. Second, making things Facebook official automatically makes this more complicated. It’s just… leave it off social.


11. You don’t need advice from your friends for everything.

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When I was in college, I relied on my friends for advice every moment of the day. I didn’t send a text to a crush without asking them about it first. It wasn’t until my 20s that I realized this was a problem. I wasn’t following my heart or doing what I felt was right – I was doing what my friends told me to do. It’s fine to ask for advice when you need help, but you also have to know how to find your own way.


12. Sometimes your girlfriends will feel like a better relationship than anything romantic.


I know this sounds so lame, but it’s SO true. The best thing about my single years, hands down, was my best friends. I bonded with them so much and created so many memories I wouldn’t have if I had been in a relationship for that time. We did everything together. We told each other everything. We knew everything about each other. We were in our own platonic “relationships” with each other, and it was the best. It’s hard to get that close to a girl friend when you’re in a relationship. Not impossible, but hard.


13. You should step out of your comfort zone.

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I’m not saying you shouldn’t know what you want, and of course you need some standards. But give people a chance! Go on a date with the dude who has the job you hate. Have a conversation with the person who is cute but has opposite political views as you. When I met my current boyfriend, I didn’t want to give him a chance. He was younger than me, he lived in the town I didn’t like, and he had the same name as my dad (mortifying). I tried to blow him off, but my best friend encouraged me to go on one date with him. So I did, and we clearly ended up hitting it off. Five years later, we’re still together. If I didn’t step out of my comfort zone, who knows where we would be?


14. At some point, you will become obsessed with the idea of the future and you won’t understand why.


When I was a few years younger, I told everyone that I would never be that girl who thought about wanting to get married all the time. Then a few friends started getting engaged, and I started being that girl. As the people around you get engaged, get married, have kids, and start adult lives, you feel the pressure, whether you want to or not. You’ll have days where you don’t give a eff, but you’ll also have days where you care. A lot. And it’s uncomfortable. But you can get through it!


15. Meeting someone at a bar almost never works out.


When you’re in your 20s, you’ll probably go to a decent amount of bars and clubs. Movies and TV shows make it seem like a bar is a great place to meet someone cute and perfect for you. This is almost never true. A bar is a great place to meet a creepy dude who wants to have sex with you. It’s the best place to meet a desperate guy who went out with the goal of finding someone to talk to. It’s the best way to meet a drunk dude who will take your phone number then forget to call you. Trust.


16. What you want in a relationship will change.

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When you’re in your early 20s, you think you’ve done all of the growing you’re going to do. Not even close to the truth. By a few years in, you’ll be a different person who wants different things – even in the dating world.


17. Settling becomes easy, but that doesn’t mean you should do it.

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As you get older, settling becomes easier because you feel more pressure to meet someone. When you’re 17 and you break up with someone, you know that logically you have a lot of time to meet other people. When you’re 26 and half of your friends are engaged and you break up with someone, you feel very hopeless and alone. It becomes easier to settle because you’re tired of going on first dates and being single. You just want someone there, and so you settle. But please don’t. No matter how old you are, settling sucks. And you deserve better – and you’ll find better.


18. You’ll watch friends – and yourself – go through some pretty shitty things.


You might think that people get smarter about dating as they get older, but they usually don’t. And so, you’ll watch a lot of your friends do stupid things, stay with people they shouldn’t stay with, and get totally screwed over. It will happen to you too. It sucks.


19. Being single can make you feel hopeless…

tina fey

Being single in your 20s may be rewarding, but it’s not always easy. Sometimes you’ll feel very alone and miserable. That’s normal. It’s just part of being single.


20. But it truly is so important.

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I know I sound like your boring grandma, but I promise you’ll get through this… with lots of amusing stories.

Which one of these things do you disagree with about dating in your 20s? What did we forget to include? Let me know in the comments.

You can follow the author, Jessica Booth, on Twitter or Instagram.


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