Dating in your 20s (and how to make it not suck)

There are some phrases so dastardly… so vile… so repulsive… that we refrain from uttering them out of a responsibility to be polite members of society. Coincidentally, the words “dating in your 20s” might just be one of those phrases. Of all the miserable things out there, finding “the one” at the height of your third decade on this planet may just be the most miserable experience of all. 

Okay, that might be a little melodramatic. The truth is, dating in your 20s can suck, but only if you WANT it to suck. While dating in your 20s might sound like a hellscape of awkward nights out and unsatisfying bedroom exchanges, the process can actually be fun, if you’re open to it. In fact, there’s likely someone out there who shares your interests, passions and ideas, and they’re dying to meet you. 

But how do you cut the crap and FIND that special someone? Strap in and start scrolling, because we’re about to race through a crash-course on dating correctly in your 20s. 

Dating in your 20s: how to do it in 5 simple steps 

Start with a positive mindset

I hate to be the one to have to tell you this, but… if you’re moaning and groaning about dating in your 20s, you’re doing something wrong. Going into a date with a pessimistic mindset is probably the WORST way to get stuck in the dating hell-loop of terrible, boring first dates. 

That’s because if you go into a date assuming the worst, you’ll probably experience exactly that. Think about it: is your date really going to give you a chance if you look miserable, disengaged, bored and checked out? More than that, are you really going to notice someone special if you’ve already written them off as awkward or uninteresting after the first conversational lull?

Try to imagine things on the other foot. Would you want to date someone who’s over you the moment they shake your hand? Heck no! So, from here on out, make a solemn pledge to give every date a chance. See what they have to offer, and once you know more, you can make a reasonable decision about them. 

And if that sounds like pulling teeth to you? Then it’s time to give dating a break for a hot second. Rest up, recharge and don’t hit the dating fields until you’re back in the right mindset.

Give up on balance 

Bear with me. I’m going to say something crazy right now. When you’re dating in your 20s… the LAST thing you want is balance. I know, I know… it sounds wrong, doesn’t it? But it’s true. Instead of looking for a perfectly “balanced” person who’s even keel and mild-mannered, look for someone who has a lot to offer in life. 

That doesn’t mean you have to date somebody wild. But dating someone with an open mind will make dating in your 20s far more fun. If we’re getting metaphorical, think about dating as riding a seesaw: if you and your partner are perfectly balanced, the seesaw is at rest, and life is… well, boring. 

By contrast, someone who is open to new experiences, likes different kinds of dates, shows you new things and excites your mind is akin to a seesaw in motion. The relationship is moving, changing and GOING places… and that’s what you want. 

After all, you have your 30s, 40s and the rest of your whole life to settle down and be at rest, don’t you? Don’t settle at 25. 

Make agreements, not boundaries 

Dating someone new makes it hard to set boundaries. Is it okay for them to sleep over on the first date? Should you pay for the meal each time, or do you trade off? If they’re a smoker, can you ask them not to do it around you? 

If you like someone but you’re struggling to set boundaries, it’s time to think a little differently about drawing lines in the sand. Instead of making a boundary — such as saying “don’t smoke around me” — try making an agreement instead. Tell your date, “it’s totally fine if you smoke, but when you do, I’m not going to be around for it. I don’t like the smell, and it’s not for me.” 

The reason this is important is because it redirects your dating energy in a more positive way. Instead of spending your time and effort preventing your date from doing something, you’re simply telling your new flame how you’re going to act around them. They can do exactly as they please, but if they want you around, they know what they need to do. 

Instead of creating a boundary that amplifies the friction between you two, you’re making an agreement that’s opening the door to better communication — and with great communication comes lasting love.  

‍Remember that everyone’s goal is the same 

What does everyone want in the end? Money? Love? A new car? All three at the same time?

WRONG. Those might be nice things… fun things… and things everyone likes… but they’re not what we all want. 

What all of us want are generally the same things: peace, comfort and happiness. That last one is crucial — everything we do in life is in the pursuit of being as happy as possible as much as possible. The rest is just filler. 

That’s the same kind of mindset you should bring to every date you go on. To find out if they’re the right “fit” for you, think about how happy they make you. Do you smile around them all the time? Are you laughing a lot? Are you genuinely enjoying yourself regardless of what kind of date you’re on?

The truth is, dating in your 20s exposes you to a lot of people who know how to make your life a little miserable. With all the uncertainty and life changes everyone is going through, looking for love can feel a bit like being thrown into the deep end and waiting for the riptide to drown you. 

But happiness — true happiness — is like a surfboard in the storm. It’s what keeps us afloat. It helps us stay above water, and stops us from drowning. And all of us are looking for our own surfboard. So, as you move through the dating world, always remember: despite different approaches to get there, everyone’s goal is the same. 

We all want to be happy, and with the right mindset, we can. 

Take a swing at journaling 

Did you know most of us are better at contextualizing things when we write them down? We’re a narratively driven species, and we like turning our experiences into written stories. Doing so has been reported to lower our stress levels, increase our creativity, improve our mood and help us make better decisions about our circumstances. 

For all of those reasons and more, it might help to start journaling about your dating experiences. There’s a lot of different ways you can do this: you could try writing down a list of all the qualities you want in a partner… writing about what your ideal “date” would look like… journaling about where you’d like to see your love life a year from now… or, if love’s not working out for you right now, you could journal about all the other things in your life that you are finding success with at the moment. 

The trick is to use your journal as a life tool, instead of just a love tool. Catalogue your dates, your ideas, your passions and your innermost thoughts. What’s working well for you? What isn’t? Get it all down — on paper or online. 

That’s the beauty of a journal. It’s a helpful tool that can be used in so many ways. The goal is to get into the groove of journaling now so that you can use it as a life habit long after you’ve exited your 20s and entered a new stage of life. Trust me: not only will you appreciate the clarity it brings to your life right now, but it’ll also be a wonderful memento to look back on when you’re happily dating (…maybe even married…!). 

Don’t dread dating in your 20s

Dating in your 20s doesn’t have to be as scary as all the doom-and-gloom blog writers make it out to be. As someone who’s been actively dating in their 20s for some time, I’ve learned to embrace and enjoy what it means to meet new people and get to know them. Some of them have been a little disappointing, but a great deal have also been fascinating individuals whom I’ve been lucky to know. 

Now it’s your turn. What will you find out there? (Or, if you’re not ready for that step just yet… drop us a line and let’s talk about how to get you into the dating scene for real!). 

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Prefer to keep it single for now? Check out our article on finding joy in being single.