Expectations versus outcomes: The dating experience

After seven years, I’ve decided I don’t want to be single anymore. So, I’ve put myself back onto the market.

Which, in practical terms, means dating apps (which, by the way, are the worst), and maybe trying something different like Table for Six — which I haven’t done yet, but can’t possibly be a worse experience than dating apps.

Putting myself back out there has been interesting, not just because of the thought of dating itself, but because it’s forced me to look more closely at expectations — especially the ones we quietly attach to romantic experiences, people, and outcomes.

Because we often step into these things with a story already written.

“This might be fun.”

“This might feel exciting.”

“This might go somewhere.”

And when the experience doesn’t quite match the internal script, there’s disappointment. Sometimes obvious, sometimes subtle. A flatness. A sense of, “oh… I thought this would feel different.”

What I’ve started to realize is that the disappointment isn’t really about the moment or the experience itself. It’s about the meaning I attached to it before and after it happened.

Somewhere along the way, I’d outsourced how I felt about myself to an external outcome. If this goes well, I’ll feel good. If it doesn’t, I won’t.

That’s a fragile way to live.

I’ve always believed that if you focus on the process, the outcome will take care of itself. But this morning I’ve been sitting with a realization about my dating: if what I seek most in my life is to feel good about myself, then this new adventure of mine has more to do with that, and less to do with finding a person.

And if that’s true, dating becomes less about hunting for a result and more about how I move through the process. Less about forcing connection, and more about staying aligned with who I am, what I am, and how I want to be.

And when I focus on that, the finding of that person becomes less forced and more natural. Not something I chase, but something that emerges along the way.

And if that’s the real outcome I’m seeking, then the process matters even more than I thought.

You don’t feel good about yourself because things work out. You feel good about yourself because you don’t abandon yourself while they’re unfolding.

That distinction has been important for me.

I used to believe that when it came to moving from being single to part of a couple, feeling good would come after something happened. After clarity. After certainty. After being chosen.

But that keeps your nervous system permanently leaning into the future, scanning for signs that you’re okay.

What I’ve been reminded of today is that feeling good about yourself is built moment by moment, through how you show up — not through what happens next. And that this principle is just as relevant in dating as it is in other parts of my life.

It’s built by staying aligned internally. By acting in a way that feels true to who you are, what you are, and how you want to be. By not contorting yourself for reassurance or editing yourself for outcomes. By not attaching your sense of worth to things you can’t control.

But that doesn’t mean I stop wanting connection — because I thrive on connection. And it doesn’t mean I stop caring, because I do care.

It just means I stop asking the outside world to regulate how I feel about myself within this dimension of my life.

So maybe this chapter isn’t really about finding someone at all.

Maybe it’s about learning how to sit across from another person — or sit alone at the end of the day — without needing the moment to validate me. About enjoying a conversation without deciding what it means. About going on a date that doesn’t go anywhere and still going home feeling intact. About having a quiet night to myself and not reading that as failure.

Because when I stop asking each moment to become something more, I actually get to experience it for what it is. And when I stay aligned with myself, connection will actually feel lighter, more natural and less forced.

Because the real work is staying aligned while life unfolds. That feeling good about yourself doesn’t come from being chosen, but from choosing not to leave yourself. And that hope doesn’t live in the future — it lives in the way you show up today.