You’ve done the hard part. You’ve started a conversation with someone on an online dating app or website, you planned a meet-up, and you’ve had a successful first date. What’s next? Another hard part (in case you haven’t caught on… dating can be difficult sometimes): asking someone out on a second date.

I recently shared a great example of how to ask someone out on a second date. After the first date with someone new, the guy (in this case) messaged my client (a woman) starting with a quick inside joke about the meeting: “Saw you finally, albeit only after you found me,” referencing who spotted whom first.

He continued, “Thanks again for a lovely evening. It was a pleasure to meet you and start to get to know you a little bit. I’m definitely excited to see you again and learn more. Perhaps Wednesday or next Sunday if your schedule permits.”

Let me tell you why this is a perfect first date follow-up:

  1. It does a great job of telling the person that he had a great time on the date and is very interested in meeting again.
  2. The message gives a few options for dates to get together again but with flexibility.
  3. It’s short and to the point.
  4. It allows an opt-out in case my client didn’t want to see him again.

Direct and honest communication is such an overlooked yet simple tactic in dating. This message had no ambiguity (leaving the other person wondering, “Did he like me?” or “Does he want to see me again?”) but also didn’t force a second date — it expressed the person’s intentions and hopes but left room for a reply or other ideas.

Another great way to text someone about a second date is by coming up with a suggestion based on something you found to have in common. If it turns out that they’re an air hockey champ, maybe you suggest heading to the arcade for a face-off.

Another client recently asked me, “One place where I struggle is where/when/how to ask for a second date. Do I do it during the first date or over text later?” And here is how I answered: “Over text later. Say at the end of the date, ‘I had a great time and would love to do it again. I’ll be in touch tomorrow.’ It gives her a night to think about it, and then it makes you a man of your word when you actually get in touch tomorrow. Win-win.”

But remember that no matter how well-crafted a message asking someone out on a second date is, sometimes the sparks just aren’t there. When this happens, it’s important to let the other person know and not ghost, or ignore, them. You can write a simple message like, “It was nice meeting you the other night, but unfortunately, I didn’t feel the connection I’m looking for. I wish you all the best.” Like the second date ask, it’s direct and honest, leaving no room for speculation or “What did they mean by that?”

Of course, I’m hoping these two go on that second date — in fact, I want everyone to go on the second date if you’re even on the fence about it. First dates can be nerve-wracking, and a second date might be where you both relax a little bit more and go beyond surface-level conversations, getting to know each other better. The outcomes of a second date are undeniably win-win: you either are pleasantly surprised at how well it goes, or you confirm for yourself 100% that this person is not a match. Who knows? You might be figuring out the best message to plan a third date.

The Right (No Ambiguity, No Pressure) Way to Ask Someone Out on a Second Date
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