The Challenges of Dating In Your Late 20s and Early 30s

By Group November 14, 2019

Ah….dating in your late 20s and early 30s…


In some ways, it’s great. Many people report enjoying sex more as they get older, people become more sure of themselves…


In some ways, it’s SO much easier than dating in your early and mid 20s, but in other ways, it’s harder.


We took a look at the top challenges people face when dating in their late 20s/early 30s, and ways to overcome them.


1) You May Feel Pressure to Boo Up

Nothing like attending 90 weddings in one summer to make you feel like you need to find a boo, and fast.


*Everyone’s doing it, so I should be doing it too*


The fact that friends may be less available because they’re spending time with partners, or getting pregnant and having babies, only compounds this feeling.


BUT: experts say that about 39% of marriages will end in divorce. And a 2014 study from the National Opinion Research Center at the University of Chicago found that fewer than 60 percent of people reported being “very happy” in their relationships.


So remember to breathe, and don’t rush things just because you feel like you need to be in serious, longterm relationship. Rushing something that isn’t right will likely result in negative consequences.


Also remember: the grass is always greener. Your married friends may be looking at your situation and thinking, ahh, if only I were single again. Relish in the freedom you have!


2) You Probably Have Less Time

For many of us, our late 20s/early 30s is when things are really kicking into gear. We’ve let go of the “what the fuck do I do with my life?!” that is so stereotypical of the early 20s, and we’ve honed in on things that matter to us. Maybe you’re in grad school, maybe you’re busting ass at your job, maybe you’re hustling to get some creative projects going, maybe you’re investing deeply in an amazing community. Whatever it is: you don’t have tons of time to spare. And dating takes time. So what do you do?


Shorter first dates: The shorter they are, the more people you squeeze into your busy life. Schedule first dates that will lost no more than 45 mins – an hour. If it’s going well and you have to cut it short, you can see them again and make some more time for date number two. If it’s not going well, then good thing you have bigger and better things to do!


Try being more firm with your boundaries / standards: Less time in general means less time for BS, rude people, and disrespect. If you’re getting weird vibes, if red flags are popping up…NEXT! You don’t have time for riffraff.


3) Attraction & Chemistry Might Not Be Enough

If you’re looking for a longterm relationship that involves marriages and kids, than unfortunately attraction and chemistry is no longer enough at this stage.


Ahhh they’re the best. They’re so hot and fun to hang out with. That’s great. But is this person someone you want to co-parent with? Is this someone you’d trust to buy a home with? Most importantly: is this someone whose life goals align with yours?


If you know that you’re looking for, be up front with people you’re dating, and ask them. Make sure you’re both on the same page before you get invested. Because maybe you want an open relationship and that’s something they’d never consider. Maybe they want kids and you’ve already decided that’s never going to happen.


One of the hardest parts of dating is accepting the longterm incompatibility of a person who is otherwise wonderful, sexy, and charming. But sometimes, that’s what you have to do.


Do you have advice on dating in your late 20s and early 30s? Let us know at


Stay positive XOXO