Dating In Your Twenties: The Chaos, Comparison & Clarity

Your twenties. The decade everyone claims is for “finding yourself,” making questionable decisions, trying oat milk for the first time... and apparently, dating a lot of people. Unless, of course, you’ve been in a long-term relationship since your teens.

Whether you’re single, coupled up, or somewhere in between, dating in your twenties can feel like a full-blown fever dream. One friend’s planning a wedding, some are having babies, another is deep in their “year of healing,” and someone else is ghosting faster than you can say “situationship”. The universal vibe? Confusion, with a side of chaos.

Comparison is the thief of joy… and your self worth

Social media is a breeding ground for comparison and when it comes to relationships, it can feel like everyone else has their love life figured out. We’re not comparing our relationships to reality anymore, we’re comparing them to TikTok's. It’s almost impossible not to compare when with one scroll you’re hit with perfect couple selfies, engagement announcements, 5am workouts together, and “Boo Basket” worth more than your rent.

Maybe you’re not vibing with anyone right now, or dating apps are starting to feel like a full-time job with no benefits. We get it! It's easy to feel like you’re behind or doing something wrong. But ultimately, you’re comparing your real life to someone else’s highlight reel. Behind every perfectly filtered couple selfie is a messy, real relationship with communication breakdowns, doubts, and (hopefully) growth.

Being single isn’t a waiting room for real life. You’re not stuck... you're in process. Healing, growing, figuring out what actually feels good and right for you. And one day, you’ll look back and realise this season shaped you in all the ways that made the real thing feel safe, aligned, and easy when it finally arrived.

In a Relationship? You’re Still Allowed to Question Things.

There’s this unspoken assumption that being in a committed relationship in your twenties means you’re “missing out.” But let’s be honest? There’s as much chaos in a committed relationship as there is dating six people whose names you can’t remember. When you’re in your twenties, the element of the unknown can be really overwhelming.

Yes, relationship doubt is real. Questions like:

• How do I know if they’re The One?

• What if there’s someone better out there?

• What if I change? What if they do?

  
  

These aren’t red flags, they’re human. Especially when your career, identity, and dreams are all still evolving. Just because you don’t have a five-year plan doesn’t mean you need to jump ship. Uncertainty doesn’t have to be a threat, it can be an invitation to grow together.

The truth is, you’re still figuring things out and becoming you! You’re still growing… still learning what you want, what you need, what your boundaries are. The only difference is that maybe now, you have someone by your side. Hopefully, someone who sees all the messy, in-progress parts of you and loves you anyway.

You're not behind. You're not ahead. You're just… on your own timeline.

And that? That’s more than okay!

Feel the need to talk out your situation, want to stop second-guessing yourself or your partner, or are just curious about what a healthy, aligned relationship actually looks like for you, try a Love Clarity Session with one of our relationship coaches. No pressure. Just space to untangle the confusion and get back to what really matters - you.

🤎 Book a session here.

Written by Charlie,

Our Community Co-ordinator at The Love Collective and Tailor Matched. Charlie brings together creativity and strategy to help shape our brands. Her mission is to inspire and support others as they navigate the path to authentic and fulfilling relationships.