Why I never thought I’d date a 20-something

Why I Never Thought I'd Date A 20-something

//Me and my 20-something man playing in LA circa 2013//

If you asked me when I was 21 who my serious relationship out of college would be with, I would have told you without an ounce of hesitation: “Well no one my age, that’s for sure.”

I had myself convinced I would date older. That by the time I was dating in my twenties, I would have found a 30-something, or (shriek sorry mom) 40 year-old silver fox to officially (and comfortably) enter into adulthood with. Call it superficial, or perhaps the result of always being told I acted “old for my age”.

So you may find it ironic that for the last four years, or the entirety of my post-college life, I’ve been with man barely two years older than me. Yes. I’m hopelessly in love and seriously dating a 20-something.

On the plus side, he has sprinkles of grey hair which gives me solace…sometimes.

When I think back, I often wonder why I had so much drama with the 20-something male. And then I think, how could I NOT have? I had just spent four years of college watching them get drunk and make asses out of themselves. These men needed years of detoxing and polo burning before they could ever be a quality addition to society, never mind a solid adult boyfriend.

Or so I thought.

Imagine my surprise then, when my boyfriend came into the picture. We met senior year of college and started dating almost immediately after graduation. We were both basically broke, buried in student loan debt, and figuring out what we wanted to do with our lives. We lived in old apartments, ordered Dominos pizza almost weekly, and spent our weekends in Netflix movie marathons because we didn’t have money to do anything else. He struggled finding a job, and I stressed out about finishing grad school. Fast forward just a year and a half later to us both laid off from our first jobs out of college and knee deep in what the kids like to call a “quarter-life crisis”.

date a 20-something

If this sounds like a hot mess, it’s because it was. At times it still is. As most of us are painfully aware being a 20-something at the beginning of your career, trying to find your purpose in the world, well it’s messy. And relationships are anything but grown up and sophisticated. My boyfriend and I got together when we both still had a lot of growing up to do. It was everything I had hoped to avoid in my post-college relationship.

It also happened to be better than I could have ever imagined.

You see, I had fantasized about falling in love with someone who already did all that growing up crap. That it would be easier to figure out my life knowing the person I was with was already established in their career, paid off their loans, maybe owned property, and was very much over the college bachelor scene.

Sure this sounds great, and it’s possible that it’s actually something I would have liked. But today I can say that I’m so very grateful I spent the last four years being messy and broke with my 20-something man.

Despite our young age, we were able to truly support and understand one another the way only people who are experiencing the same thing could. Sure we had, and still have, a lot of growing up to do, but we did the hardest parts together, side by side. That’s just something you don’t experience as intimately when you date older. It’s something very precious that I didn’t factor in until I experienced it myself.

So yes, I’m the girl that never wanted to date a 20-something, but hey, I’m happy to be proven wrong.

My relationship changed my perspective. We survived some hard years, and I’m here to tell you – there’s something to be said for growing up together.  All the challenges that go hand-in-hand with being in your twenties didn’t tear us apart, instead they brought us closer as a couple. So if this post makes you give that shaggy haired entry-level account executive another chance, then perhaps I’ve done my job.


What’s your experience dating a 20-something? Share you thoughts and stories in the comments below!