May 31, 2023

Ten Unspoken Rules on a First Date.

At 48 years old and still unexpectedly single, I’ve been on more first dates than I ever expected to go on.

And as someone who was named top bachelor in Denver area wayyy back in the day, I’m something of a veteran (sadly, perhaps). More to the point—and this is key to anyone daring to give advice on first dates—I’ve also been on many second and third and fourth dates.

So: here’s a little advice from me and “my” friends.

Generally: Be honest. Be kind. Be thoughtful. Be funny. Be self-deprecating. Take a deep breath. Listen. Do something fun, relaxing. It’s not a job interview.

With thanks to the crowdthinking over at Reddit, plus a few I’ve added in from my own experience/ethics.

  1. Your phone is not part of the date.
  2. Shower before. Go easy, if you use any at all, with the perfume/cologne.
  3. Don’t drink too much.
  4. Both should know it is a date. It’s nice to be subtle, friendly, but it’s also nice to be clear, and enjoy the tingle tension of flirting mutually. What’s not nice is unnecessary confusion.
  5. “Not a rule but. Never make the other person carry the conversation. You’re both here to make an effort and give each other the respect. If you both want different things then let it be said after. No need to hurt someone’s self respect for your ego.” Err on the side of asking questions and listening.
  6. A common one: Don’t talk about exes! Not sure I agree with that one. If you do, be respectful and fair. And…don’t go into depth (98% of your convo should not be about exes). I like this take: “You can absolutely talk about exes but make sure the information you’re giving is beneficial for both of you. Don’t vent.”
  7. Do something fun (click here for ideas), that you’d enjoy doing even if the date isn’t great. A sit down formal dinner is not a great first date unless you already know each other well. Better: food truck, ice cream, hike on a popular trail, coffee, art gallery opening, farmers market. Something not too private, where both parties feel safe is important (men don’t always think about this, but this is something to be considerate about). That said, you still want to be able to focus on each other, so don’t get toooo social.
  8. Don’t be shitty to waiters/service staff. That’s some good advice for life, generally.
  9. Don’t catfish them
  10. Go dutch. Or pay, if you’re the man, and you want to. But it should not be expected. She should offer.


“First dates are thin, eager, weak, sweet, young…full of real but ephemeral love. The tired heart warms again and, childlike, a naive hope of love buds up.

Second dates are a time to talk, a time to get to know—a time to see if the avocado soaked in clean water in a jam jar set on only two toothpicks in the warm sun will sprout. You have to wait two weeks, sometimes.” ~ Things I would like to do with You.

Read 7 Comments and Reply

Read 7 comments and reply

Top Contributors Latest

Waylon Lewis  |  Contribution: 1,492,910