Dating

100+ Questions to Ask Someone Over Text

Conversation starters that actually go somewhere — and how to turn a chat into a real plan in your city.

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Texting someone new is easy to start and hard to keep going. These questions are the ones that actually open a conversation.

Questions that break the ice

Start light, then go deeper.

  1. What's the best thing that happened to you this week?

    Opens on a positive note and is impossible to answer with one word.

  2. What's a place in this city you'd take someone who'd never been?

    Doubles as a plan you can actually make together.

  3. Coffee or a walk — which is the better first meet-up?

Turning a chat into a meet-up

The questions are a warm-up. The point is meeting.

The best conversation is the one that ends with a plan.
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