Dating Challenges to Try If You’re so over Being Single

by 8ztsr

Sometimes being single feels like a blessing because getting into a relationship is the last thing you want or need. But other times, you’re exhausted by the dating game and feeling very much like Charlotte in Sex and the City when she shrieks, “I’ve been dating since I was 15. Where is he [or she, because you do you]?!” In those moments, you might realize you need to change up your usual routine, and that’s where the following 11 challenges come in. But before jumping right in, a disclaimer: being single is 100 percent nothing to be ashamed of. After all, it’s not a disease, it’s everyone’s default state. So while some of these challenges are explicitly about dating, others are about doing things that broaden your horizons in amazing ways, whether you meet someone new or not. Because really, a big part of feeling better about being single comes in realizing how much possibility there is in the world. Now, on to the challenges!

1. Let a friend control your online dating activity for one week.

Maybe don’t allow them to rewrite your entire online dating profile, because your masterfully witty lines are probably great. But have your most honest friend (who also knows your entire dating history) give the thing a look to make sure you’re putting your best digital foot forward. Then—and here comes the terrifying but probably totally worthwhile part—give that friend permission to send messages, respond to any incoming notes from promising people, and set up dates for you. Anyone who truly loves you will understand that with great power comes great responsibility, and she better not eff this up. She might see the potential in people you’d otherwise skip over, and in any case, it’s always good to shake things up.

2. Go to one cool cultural event every other week.

On the first Friday of every month, a museum right outside of Chicago would throw a huge party complete with wine and snacks, then keep the exhibitions open so we could wander around feeling tipsy, cultured, and very proud of ourselves. The best part: you couldn’t move without bumping into an attractive person. When I moved to New York, I’d go to book readings and literary events that, again, usually happened to be packed with gorgeous, smart, interesting people.

Of course, it’s not about going to these events just to meet someone. If you do strike up a conversation with a new person, the bonus is that cultural events often give you more to talk about than you’d find at a bar, and you already know you two may have common interests. But either way, if you’re into this sort of thing, the events are often so fascinating you don’t feel bummed if you didn’t meet anyone special. Instead, you’re reminding yourself you can have an awesome life, single or not.

3. Make eye contact and smile at someone every time you’re out socializing.

Sometimes when you see an attractive person, you train yourself to only look at them when their eyes are averted. It just feels so much more safe? Like if they actually caught you looking at them, you’d disintegrate into a pile of dust and embarrassment? Luckily, that’s not how it works. People often need some form of encouragement before coming up to you, and making eye contact and smiling is one of the easiest ways to give it. Think about it, if they’re not interested, how can they actually humiliate you? Oh, that girl looked at me then smiled, she’s delusional, padded room for one? No. Worst case, they look away. Best case, they take it as a green light and come up to chat.

4. Approach someone once a month.

This could be online or in person. Either way, women are more than allowed to make the first move, and the right person won’t see it as something that automatically takes you out of the running. Funnily enough, I’ve talked to guys who admit it’s nerve-racking and wish women would do it first!

5. Give yourself permission to get rid of dating apps.

Dating apps are obviously a great way to meet people from the comfort of your couch. But if you’re on app overload, don’t force yourself to keep swiping out of self-obligation. Mentally exhausting yourself before you even leave the house is the opposite of constructive. Plus, if you’re in the negative mindset that often comes with making yourself date when you don’t want to, you can start giving into confirmation bias. Without realizing it, you’ll begin to believe every garbage online interaction you have is evidence that all the good people are taken. (That is obviously not true, because you are single as well.)

6. Ask your most truthful friend if they think you should do anything differently.

It’s not about doing things “wrong,” because dating is insane and unpredictable and sticking to hard-and-fast rules sometimes just doesn’t make sense. But your friends have the luxury of distance from your love life while still knowing the details, so they may be able to pick up on things you’re too close to see. The truth can be hard to swallow, but sitting down with a glass of wine and your game face on can help it go down a lot easier. Remember that they only want the best for you, and the conversation could get you one step closer to meeting someone.

7. If someone has been begging to set you up, let them do it.

Whether it’s a friend, family member, or coworker who’s saying they know someone who’s “just perfect for you, seriously, you guys are like the same person,” take them up on the offer. At the very least, they won’t be able to bug you about it anymore.

8. Sign up for an intriguing class.

There’s probably something you’re interested in learning to do better, whether you’ve never tried it before or already know you have a knack for it. Speaking Italian? Cooking? Woodworking so when you move to a cabin in the mountains, you can make your own home décor instead of paying an arm and a leg for shipping? Whatever it is, figure out where there’s a regular open slot in your schedule and fill it with a class that will make you feel like even more of a badass human than you already are. Great if it’s a class where you could potentially meet someone, but that’s absolutely not a requirement. You’ll boost your self-confidence no matter whether you make a new friend, have a meet-cute with a love match, or simply becoming better at something you like.

9. Wear your absolute favorite outfit when you need an extra confidence boost.

Forget about society’s random mandates about what’s “flattering.” When you go out, when you’re on a date, whenever, wear what makes you feel like an actual goddess. The confidence you get from wearing what makes you feel best usually sends a bigger, better message than what your outfit or makeup ever could.

10. Go to one meetup for your favorite workout each month. has gatherings for pretty much everything from hiking to bootcamp. Maybe you meet someone sexy who’s a fan of the same form of exercise as you. And if you don’t? You get a workout, potential new friends, and an endorphin rush. Not a bad deal.

11. Stop having sex with the person who makes your vagina feel good but your soul feel bad.

Unless you’re an expert at separating your physical and emotional feels, it can be easy to get so caught up in this person that you’re not open to new options. Breaking it off is the epitome of challenging, but it can be an important step in telling yourself (and the universe) that you’re ready for something life-changing and real.

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