Run Game Conversation

First date mistakes guys make, and what to do instead

Updated 5 min read

Most first date mistakes are small and fixable. A vague plan, a loud room, a phone face-up on the table. None of them make you a bad date, but a few in a row can leave someone with nothing to say yes to for a second one. Here are the usual ones, in the order they tend to show up, and what to do instead.

Before the date

Vague plans

"We should hang out sometime" and "what are you up to this weekend?" make her do the work of turning it into a plan. Name the day, the time and the place.

Instead: "Coffee Saturday at 11 at the place on Main? About an hour. Or tell me somewhere that suits you better." Then confirm the morning of with one short text. How to ask someone out has more lines.

The wrong venue

Common culprits are a loud bar, a movie (you won't talk), a long dinner, or a place so crowded you can't get a seat. A first date is mostly for finding out whether talking to each other feels good.

Instead, choose somewhere quiet enough to hear, with seats, that costs little and ends on its own. Coffee, a walk with a drink, a food market. Visit it once beforehand so you know where to sit. First date ideas lists options, and micro-dates (20-minute first meets) are a good low-stakes version.

Running late with no word

Being on time is an easy win. Arrive five minutes early. If something goes wrong, text as soon as you know: "Running 10 late, sorry. Order something and I'll get the next one."

During the date

Phone out

A phone face-up on the table says something even if you never touch it. Checking it says more.

Instead, put it in your pocket on silent before you walk in. If you're expecting something real, tell her in the first minute: "My sister's flight lands tonight, I might glance at this once." Then glance once.

Interviewing her

Question after question can feel like a job screening, and she learns little about you.

Instead, answer your own questions, and say statements between them. "I walked past this place for a year before I came in" does more than another "so what do you do?" See first date questions for what to ask and how to trade answers.

Monologuing

The opposite problem. You're nervous, so you talk, and twenty minutes goes by. Stories are great, but a long one with no room for her to react turns the date into a talk.

Instead, keep stories under a minute, then hand it back with a question. If she's leaned back and gone quiet, that's your cue.

Too much drinking

Drinking to take the edge off can backfire. You may read signals less accurately, repeat yourself, and say things you'd skip sober.

Instead, cap it at one or two, and match her pace. If she isn't drinking, don't comment on it. If you're the one skipping alcohol, a soda is fine, and nobody needs an explanation.

Talking about your ex

A long account of the last relationship, or a list of what went wrong, can read as though you are still in it. Complaining about exes in general can make someone wonder how you'd talk about them later.

Instead, if she asks, give one calm sentence ("We split a year ago, it ended fine") and ask about her.

Pushing physical contact

Reaching for a hand, a hug that lasts too long, or moving closer when she's leaning away. Consent matters here and it's simple: if she pulls back or says no, stop and carry on as before.

Instead, read her. If she's leaning in, touching your arm when she laughs, holding eye contact, then a light touch on her arm or a hug at the end is a reasonable next step. If you can't tell, ask before a kiss: "Can I kiss you?" The signs are in how to tell if someone is interested in you, and consent and respect goes further.

Who pays

There's no single rule everyone follows, and you can't know what she expects. Keep it simple and low-stakes.

The end of the date

No plan for the end

Drifting out of a cafe with "uh, I guess I'll see you" leaves both of you unsure whether it went well.

Instead, decide at the 45 to 60 minute mark. If you want more, suggest a specific next step: "I'm not ready for this to end. Want to walk to the park?" If you're done, wrap up on a high note. Say what you enjoyed, then leave first. If she says she needs to go, you go.

No follow-up

Waiting three days so you don't seem eager can just leave her wondering. If you had a good time, say so within a day.

Instead, text that night or the next morning: "Had a good time. Want to do that again Thursday? I'm thinking a walk and food." If she doesn't reply, one friendly follow-up after a few days is fine. After that, let it go. Ghosted after a date covers what comes next.

If you didn't feel it, you don't owe a long explanation. A kind "I had a nice time, but I'm not feeling a romantic connection" is better than silence.

What to do next

  1. Write your standard ask in your notes: day, time, place, length. Keep it under 30 words.
  2. Pick two go-to venues you've visited once, with seats and a quiet corner.
  3. Put your phone on silent and in your pocket before you walk in, every time.
  4. Set a limit of two drinks and decide it before you arrive.
  5. Prepare one calm sentence about your ex, in case she asks, then move on.
  6. Choose your end point in advance: 45 to 60 minutes, then either a specific next step or a warm goodbye.
  7. Send the follow-up within 24 hours, and write one line about what you'd do differently.

If you keep notes on your outings in Run Game, a session's notes field is a handy place for that last line, and the forum's Dates topic is open if you want a second opinion on a date that went sideways.