I get asked some version of this more than you’d think. Usually in the booking process, sometimes right before we meet… occasionally in the middle of dinner by someone who’s clearly been thinking about it the whole time. “What should I do?” “What do you like?” “How do I make this good?”
And I always want to say the same thing… you’re already overthinking it.
Not because I don’t care how the night goes. I care a lot, actually. But the best dates I’ve had weren’t the ones where someone showed up with a game plan. They were the ones where someone showed up as themselves.
Pick a Place You’d Actually Want to Go
One of my favorite dates started at a restaurant I’d never heard of. Small, kind of tucked away, nothing flashy. There was a balcony overlooking a lake and maybe six other tables. He picked it because he’d been there before and loved it… not because he Googled “impressive date restaurants” and chose the one with the most reviews.
That matters more than you think. When someone picks a place they genuinely like, it tells me something about them before they’ve said a word. And honestly… I’d rather sit across from someone who’s excited about where we are than someone who booked the expensive place because they thought they should.
I don’t love loud restaurants. I want to hear you talk. A gorgeous view and a table where we’re not shouting over someone else’s birthday party… that will beat a trendy prix fixe every single time.
Be the Version of You That Your Friends Like
Here’s the thing I wish more people understood… trying to impress me almost never works. I can feel it. There’s this specific energy when someone is performing… choosing their words too carefully, ordering wine they don’t actually want, sitting up a little too straight. It’s not bad. It’s just not fun.
The dates I remember are the ones where someone told me about the weird hobby they’re into, or laughed too loud at their own joke, or admitted they have no idea what half the menu says. The ones where someone was a little goofy. A little unfiltered. A little them.
You have people in your life who genuinely enjoy your company. Whatever version of you shows up around those people… that’s who I want to meet.
Just Tell Me
I’m going to be honest about something because it’ll save us both a lot of guessing… my brain works in a pretty straight line. I don’t do hints well. I’m not going to pick up on the thing you’re not saying, and I’m not going to be offended if you just… say it.
If you’d rather stay in than go out, tell me. If something on the menu looks weird and you want to try it, tell me. If you’re nervous… you can tell me that too. I’ve never once thought less of someone for being straightforward with me. I have thought less of people for making me guess.
I’m a direct person and I like direct people. It’s one of the reasons I’m so easy to be around… you don’t have to perform a whole chess game to figure out what I want. Ask me. I’ll tell you. I’d love the same in return.
You Don’t Have to Fill Every Silence
Some of the best moments on a date aren’t the conversation. They’re the pause where you’re both just… there. Comfortable. Not rushing to the next topic because the quiet feels like a failure.
It doesn’t. Silence with someone you’re enjoying is its own kind of chemistry. I notice when someone can sit in it without panicking… it tells me they’re actually present and not running a script in their head.
The Short Version
Show up as yourself. Pick somewhere you actually like, not somewhere you think will impress me. Be a little weird. Say what you mean. And if there’s a quiet moment… let it breathe.
That’s it. That’s the whole secret.
The guys who’ve had the best time with me weren’t the smoothest or the most prepared. They were the ones who forgot to be nervous because we were actually having fun… and honestly, that’s all I want out of a night. Just a really good time with someone I like being around.