9 Reasons Dating in Your 20s Is the Worst

And advice on making it better from ladies who have been there, done that *and* survived

(Photo: iStock)
(Photo: iStock)

It’s a truth universally acknowledged that a single man in possession of a good fortune… is probs gonna slide into your DMs and either be a dick or send an unsolicited pic of one. And tbqh, women can be f-ckbois, too. Those are just two of *many* reasons why folks in their twenties are realizing their quest for love leaves *a lot* to be desired, regardless of gender or sexual orientation. Dating is hard, yo.

Don’t believe me? There are *several* reddit threads specifically devoted to deciphering just *why* dating in your twenties is so GD challenging, with the general consensus being that it gets much better in your thirties (thank goddess).

There are many reasons dating is so difficult, paramount being that, despite what Drake tells us about being firmly in *his* feelings,  an increasingly individualistic society has made young people fearful of “catching feelings.”  And that’s ~science~ btw. Jean Twenge, a psychology professor at San Diego State University who researches generational differences, says Gen Z (the v. hip and v. young generation born between 1995 and 2012, who she also calls iGen) are taking longer to grow up, which means they’re taking longer to date. Instead, they’re choosing to use their twenties to explore: careers, the world and themselves.

What’s more, unlike a lot of our parents and grandparents, millennials and Gen Zers can thank economic instability for the fact that they aren’t anywhere remotely ready to settle down. We’re still trying to figure out our own lives, so don’t saddle us with looking after someone else (or their student debt payments). 

But a bleak dating landscape doesn’t mean we should abandon all hope. For those who still want to give dating in their twenties a go, we have some expert tips on how to navigate the dating minefield, from some of the best in the biz: Women who have been there, done that *and* survived. That is, women in their thirties and beyond.

So, friends:

With apps, you’re never sure if your date is just looking to hook up—or forever in search of the next best thing

I personally try to avoid hook ups with any random [people]. When it comes to dating and apps, I usually wait about a week of talking before meeting up. If they are looking for a hook up then they won’t invest a week of their time” —Mariana, *almost* 30, single

Ghosting is a thing


Ghosting sucks and I really advocate that people don’t do it—unless their date made them feel uncomfortable or unsafe. Unfortunately, ghosting is normalized and the only real way to handle it is to know it’s a possibility, to know that it’s more of a societal shift than it is about you personally, and to try to cultivate resilience around it without shutting you off to the many wonderful people who are perfectly capable of using their words. It’s like every other facet of life: frustration will crop up, but the possibility of something great exists in its midst”—Claire, early 30s, married, matchmaker

Your ex (and your ex’s new partner) are just a click away on social media*

*This bad behaviour is applicable at any age, but especially common in our twenties

“This is a tough one and a trap we can all fall into, especially when the breakup was tough. It’s hard not to be curious or even insecure about your ex’s new life, so I try to add a dose of reality (and a little bit of manipulation on my own brain) with a little exercise. I look around wherever I am and ask myself: ‘What are the chances of my ex and their new love walking through my living room/home/workplace right now? Zero percent? Then let me make sure they don’t enter via social media.’ I think that the probability of running into them in real life is high enough as it is, let’s not increase the chances!”—Talya, mid-30s

There are too many unspoken rules: You have to be “chill” even when you don’t feel chill *

*Because being “too clingy,” “too demanding” or “showing too much interest” might scare people off

First of all, we need to throw out that language. All of these are gaslighting terms for real, human emotions. If you want to see someone you’re dating once or twice every couple weeks and they call that ‘too clingy’—honey, they don’t want you, they just want you to be a convenience store for their D. Your desire for quality time is not unreasonable. If you’re genuine and vulnerable and the person says you’re ‘showing too much interest’—listen to them. They are telling you they can’t be there for you in the way you want, and then GTFO. If someone isn’t going to be kind and gentle with your heart, you don’t want to give it to them in the first place”—Paddy, early 30s, in a relationship

Sometimes, it can feel like you’re someone’s mom, *not* their partner


“This is a *big* thing in your twenties because it’s not like it was for the previous generations, where by 22 you had a stable, full-time job. Our lives don’t work that way now. Your twenties are a time where you’re building. And a lot of people now—because it’s too expensive to be going to school and paying for rent, or because they want to save—choose to stay at home, which can feed more immaturity because it’s taking people longer to find a way to be totally independent.

It’s definitely on a case-by-case basis, and you’re not going to know until you actually get to know somebody. You can’t just assume everyone who lives at home is immature, but then you can’t also assume just because they have a job it means that they’re mature. You have to experiment and you have to meet people” —Lee-Anne, mid-30s, recently married, dating coach

Romance seems hella dead. Netflix and Chill is the new wine and dine

“I once had a guy open a bottle of room temperature wine while we sat in his car… Another guy took me to meet his friends at a comedy club and tried to hook up with me in the back alley where we parked. A back alley. In downtown Toronto. Every woman’s dream come true. 

Editor’s note: Or more like this…?

“Don’t settle for less. If someone asks you into their car and breaks out a bottle of wine, don’t waste your time. Run. Fast and far. My fiancée and I had our first date at a Dairy Queen on a hot summer day, we ate our frozen treats and talked about everything.  On our second date he cooked dinner, and still has the battles scars that remind me of his effort. A good partner won’t ask you to Netflix and chill, they’ll take you out, invest their time in you and romance the hell out of you (just remember to appreciate them trying). Romance isn’t dead, you’ll find it with the right person, in their own special way. Just be kind and patient.”—Janene, mid-30s, engaged

It’s tricky to balance what you want and need with what your partner wants and needs

“One mistake I made when I was in my twenties and in a long-term relationship was assuming that because we weren’t fighting about them, there were no issues or resentments building. Over time, as I changed and grew, I would forget that my partner could be doing the same. I didn’t know that there might be a need to talk about whether we were aligned or if they felt supported and fulfilled by our relationship

Now, in my thirties, finding balance is an ongoing task that requires regular check-ins. Asking my partner, ‘How are you feeling about your goals?’ or ‘Do you feel supported by me?’ might seem arbitrary at times, but I’m always surprised by how revealing these tough conversations can be; some form of growth, connection or change always comes out of them.

You have to know that you can’t control a person’s desires or ambitions—you can only assess whether you fit in with them or not. Part of this is allowing the love you have for yourself to lead the way” —Talya

App fatigue is a *real* thing

“Spend no more than 15 minutes a day on apps. And you need to only text during reasonable hours: No 2 a.m. messages, no swiping as soon as you get home from the bar. That’s not a thing because all those choices will be poor. So, if you decide you’re going to message people between 7 a.m. and 7 p.m.—that’s it. If someone messages you after that, you can message them back at 7 a.m. tomorrow.

Another tip: Be on no more than three dating sites [at one time] and spend only 15 minutes a day between all three of them (a.k.a 5 minutes per app). The goal is to get off the app, Tinder and Bumble can’t be your only tools in the toolbox. So, go to meet-ups and cool events with your friends IRL. Especially in your twenties, don’t put all your eggs in the online basket. Get out and meet people IRL—that’s the key”—Lee-Anne

Dating is expensive AF

“Dating can be expensive, but it doesn’t have to be. Look up what’s cheap and/or free in your area: museums, art galleries, music festivals, cultural societies—and lots of other organizations often have times or specific events that can be a lot of fun. Get creative! If you find yourself dating people who expect you to engage in or pay for expensive things, maybe they’re not a great match for you” —Claire

“Thoughtfulness, creativity and imagination are free. It doesn’t cost money to connect. Think about what they love and find a way to surprise them with it. Ask them to think about what they love doing and surprise you with the same”—Paddy


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