Why Is Dating in Your Twenties So Exhausting?

I don't think anyone prepared us for how weird dating in your twenties would be.

Growing up, it seemed pretty straightforward. You meet someone, fall in love, and ride off into the sunset together. Easy peasy, right?

Instead, you're trying to figure out whether someone likes you based on their texting habits. One week you're excited because you've met someone new, and the next week you're staring at your phone wondering why they've suddenly gone quiet after talking to you every day.

You tell yourself you're not going to get attached too quickly, and then somehow you're imagining your future together after five (or let’s be honest two) good dates.

If any of this sounds familiar, you're definitely not alone.

Dating in your twenties can feel like a constant cycle of hope, disappointment, excitement, confusion, and overthinking. Part of what makes it so challenging is that you're not just trying to find a partner. You're also trying to figure out who you are and what kind of life you want to build.

Maybe you're starting a career or changing careers. Maybe you're moving cities, living with roommates, travelling, going back to school, or trying to answer the question that seems to follow everyone in their twenties:

"What the heck am I doing with my life?"

The reality is that most people don't actually know. They're just doing their best to figure it out as they go.

The problem is that dating apps and social media can make it seem like everyone else has things figured out. Everyone appears to be finding their person, getting engaged, buying houses, having babies, and moving through life with confidence.

Meanwhile, you're wondering if it's normal to cry over someone who you technically never even dated.

(For the record: yes, it is.)

I think one of the hardest parts about dating in your twenties is how easy it is to make every rejection feel personal. A first date doesn't lead to a second date and suddenly you're questioning whether you're attractive enough. Someone ends things and you start wondering what you did wrong. A situationship fizzles out and you find yourself replaying every conversation, trying to figure out if there was something you could have said or done differently.

It's understandable why we do this. Rejection hurts, especially when you were hopeful about where something could go. When a connection ends, it can feel like evidence that something is wrong with you.

The reality is that sometimes two people simply aren't a match.

Sometimes the timing is wrong. Sometimes one person isn't emotionally available. Sometimes the connection just isn't what either person hoped it would be. While those things can still hurt, they don't mean you are unworthy of love or that you did something wrong.

I think one of the biggest challenges of dating in your twenties is learning how to stay open without losing yourself in the process.

It's easy to start moulding yourself into the version you think someone else will want. Maybe you ignore a red flag because you're tired of starting over, or you convince yourself you're okay with something that actually bothers you. Maybe you accept less than you deserve because having something feels better than having nothing.

I want you to remember this:

A relationship shouldn't require you to abandon yourself in order to keep it.

The right relationship won't make you feel like you have to earn your place in someone's life. It won't leave you constantly guessing where you stand or questioning whether your needs are too much. While no relationship is perfect, healthy relationships tend to bring more clarity than confusion.

If you're dating right now and feeling discouraged, I want you to remember that just because dating has been difficult, it doesn't mean you're doing it wrong. It doesn't mean you're behind. It doesn't mean you've missed your chance. And it definitely doesn't mean you're not worthy of love.

Your twenties are often portrayed as the decade where you're supposed to meet your person and have your life figured out. I think the movies we grew up watching played a big role in creating that expectation.

In reality, for many people, your twenties are a decade of learning.

Learning what you want.

Learning what you don't want.

Learning how to communicate.

Learning how to set boundaries.

Learning how to recover when things don't work out.

Perhaps most importantly, learning that your worth isn't determined by whether someone chooses you.

Because while dating is about getting to know other people, it's also an opportunity to get to know yourself. It's a chance to understand your needs, your patterns, your boundaries, and the kind of relationship you want to build.

Ultimately, the relationship you have with yourself is the one you'll carry with you no matter who comes and goes.