Ideas & guides

Real, useful guides for the fun parts of dating — what to ask on a first date, creative low-pressure ways to ask someone out, and date ideas that don’t cost much. Each one pairs with a free tool you can use right away.

52 Questions to Ask on a First Date (That Aren’t Boring) — The trick to a great first date isn’t clever questions — it’s questions that get an honest, story-shaped answer. Here are 52, sorted from easy to deep.
How to Ask Someone Out: 15 Creative Ideas That Aren’t Cringe — The best way to ask someone out is the one you’ll actually go through with. Here are 15 ideas — from a two-line text to an interactive invite — and how to pick.
50 Cheap & Free Date Ideas for Every Season — A great date is about attention, not money. Here are 50 cheap and free ideas — by mood and season — plus a jar you can shake when you can’t decide.