I know a lot of people are frustrated by how painful and miserable dating can feel. But that pain is mostly a story you're telling yourself. For me, dating has been one of the most fun things I've done all year — even after spending over $10,000 on matchmaking, apps, coaching, and a lot of dinners. If you'll lean into the fun, dating is one of the easiest ways there is to meet someone new and actually connect.
The pain is real — and it's still fun
I'm not pretending it doesn't hurt. I've had the rush of "this one is going to be it," followed by her not even responding. I know that suffering. But it's also been one of the most fun adventures of my year, and both things can be true at once. The difference is which one you choose to focus on.
Most of us forgot how to have fun
A lot of us have quietly given up on fun and slipped into a survival mindset — fear, danger, just getting through the day. Remember being a kid, or a teenager, or in college, when fun was the whole point? If it wasn't fun, you weren't doing it. You can bring that back on purpose. I went out for a hibachi and sushi dinner recently and was so excited I could barely eat — there have been very few things all year that fun. She wasn't physically attracted to me but was willing to do a second date, and I passed. If it isn't a "hell yes," it's a no.
Treat it like play
Every date is an adventure: is she the one or not? Usually not — but spotting the rare exception is the fun part. And the conversations have been incredible. Men and women have told me about their divorces, their app experiences, their whole lives. When you frame dating as play instead of suffering, you can laugh at the parts that used to sting. You're not being rejected; you're out seeing what happens. Say something, see how she responds — that's the game.
Fun makes you want to keep going
Here's the payoff: the more genuinely fun you have, the more you want to do it again — even after you get your feelings hurt, even after you get excited and then ghosted. I still can't wait for the next date. I've driven from St. Pete all the way to Sarasota for one, tried new restaurants and new places, felt every emotion — and I've done almost all of it with no sex involved at all. The suffering is just a signal you're taking it too seriously. And if you can learn to have more fun dating, ask yourself what else opens up — your work, your parenting, all of it.
That's the same spirit as why dating a lot doesn't mean you're desperate: it's an adventure, not a verdict. If this resonates, you can watch my dating playlist here.