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14 Things I Wish I Knew Before Dating in My 20s

United States Student Work Couples
by Jordan McCutcheon Dec 11, 2015

“TRYING TO DATE JORDAN is like trying to lasso jello,” my father once told friends who wanted to set me up. It’s true. The past 10 years have made me that way: independent, particular, cynical, and maybe even smart. While it’s been a long, messy road from 20, I’ve made it to 29 without leaving too many of my heart pieces scattered across the globe.

I will never claim to be an expert. If anything, I’m the anti-expert. I’ve made mistakes, watched my friends misfortunes, and come out of it unscathed and single on purpose. Dating in your 20s is fun, but it’s perplexing. Here’s what I wish I knew before I entered unchartered territory nine years ago.

1. Consider what your friends and family say about your partner.

You can’t see the train wreck when you’re on the train, but your family and friends can. They’ve known you forever and recognize when your personality, moral compass, and well-being have been compromised. While you can’t let them decide whom you date, it’s worth listening to what they have to say.

2. People are insane.

It’s a hot mess in the 20-something dating jungle; you won’t get through these 10 years without having a relationship with someone who’s crazy. We all have our quirks, but this person has blatant red flags.

Maybe your girlfriend demands to know all your passwords so she can spy on your online accounts. Your boyfriend doesn’t let you go out at night without him unless he approves of your outfit. Your friends avoid meeting up with you when your partner joins. This person isn’t going to change, and it will get worse. You don’t deserve the grief that comes with their insecurities.

3. Staying out all night every weekend to meet someone will backfire.

The dad rule stands: Nothing great happens after 2am. If you’re staying out to meet someone or get another’s attention, go home. You’re drunk. Or you will be soon, which ironically makes a more convincing case in your brain to stay out later.

This can lead to an awkward morning with a) a naked stranger b) someone you work with or c) your roommate who let you sleep in her bed when she found you passed out on the doormat, shoes off, keys in the door. In each scenario your phone is missing.

4. Beware of all technology.

Internet and smartphones have made dating the worst. Technology has developed so fast that there isn’t a strict code to follow about what not to do besides your own common sense. Paranoia runs rampant when your partner sees you “liked” an ex’s picture on Instagram. That girl you had a horrendous date with can find you, “follow” you, and then physically follow you because a friend tagged where you are on Foursquare. When you do go on a date, is it fate that makes you so compatible or did he Facebook stalk you first?

It’s easy to blame technology, but Tinder doesn’t compel the man using the app to send you a dick pic. There’s a person behind each of those screens. Assume everyone is creepy. Unplug once in a while and make your accounts private.

5. Nude photos are a risky business.

Sending naked pictures may seem like a swell idea when rekindling the passion of a dying flame in a long-term affair or just because you’re bored at work. Either way, the consequences can be drastic.

What if the relationship has a tumultuous demise? How much do you trust the person on the receiving end? If you’re still debating whether to hit send, some things to consider: the photo going public, blackmail, your father’s disappointed face.

6. Chemistry is a beautiful danger.

The hottest drug at any party is the person who can make you feel hot, hot heat to your core from across the room. But remember that kind of attraction is a powerful emotion that can make you impulsive and incorrigible. The sex is so mind blowing it’s addictive, and you forget anything else matters like work or class or perhaps that you already have a boyfriend.

It’s not love. It’s lust, and it will ruin you like black tar heroin.

7. Define the relationship.

At some point in the past decade, it became a sign of weakness to admit how you feel about someone. It’s led to a culture well versed in hooking up and maintaining a blissful state of disillusion about what “we’re just having fun” means.

Know you can handle just hooking up or you’ll be a year into the “relationship” wondering why you haven’t been on a date yet. By that time, it will be too complicated to make exclusive because you’ve spent so long pretending you don’t care about each other. If you want commitment, don’t be too afraid to ask your partner. You might get thrown to the curb, but if that’s what happens you deserve better anyway.

8. Stop comparing yourself to others’ love lives.

Being in your 20s is weird. There’s never another time in life where people the same age are on so many contrasting relationship levels. Somewhere after college graduation and the quarter-life crisis, friends start getting engaged and being pregnant while you’re like, “I think I’m going to move to Mexico for a while.”

And that’s fine. Getting married and starting a family shouldn’t be a race. You’ll either find someone or you won’t; if you’re in the latter (single) category, remember you have a ton of company. So pass the vino and enjoy the alone time before you have to share your side of the bed with someone forever.

9. Don’t settle because you’re bored or lonely.

You’re too young to ruin these precious years stringing someone along who’s just as boring as the rut you’re stuck in. Instead, take time off from being in a relationship except for the one with yourself. Master the art of independence. Learn to be alone. It’s a trait not everyone possesses, and, unlike the Bumble match you found while serial dating, it’s useful to your future.

10. Stop sending messages if there’s no response.

When you’re into someone, it sucks to see they’re ignoring you. And now you can tell because ‘seen’ notifications exist. The more texts you send, the more annoyed he/she will be. It’s as easy as that. Accept the other person isn’t interested, and stop wasting energy messaging them or checking your phone to see if they wrote back.

11. Utilize the unfollow button.

Breakups are rough. They’re even worse when you can watch as your ex’s happiness with a new partner oozes across your newsfeed. Before you get sucked into the black hole that begins by clicking on the picture, hit unfollow and let the forgetting begin.

12. Don’t complain about how awful/sad/upsetting your love life is on social media like a teenager from 2002 with her first AIM account.

This is the equivalent to what owning a bunch of cats and living alone used to mean before Taylor Swift. It’s sad but in a way that no one feels sorry for you.

13. Recognize when you’re the only one giving.

Relationships are about compromise and sacrifice on both ends. If you realize you’re the one committing without anything in return, you owe it to yourself to get out.

14. Regret nothing.

You’ll embarrass yourself, kiss a lot of awful people, have your heart broken, and destroy someone else’s, but in the process you’ll learn a lot about yourself, what you want, and what you deserve.

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