Best Questions to Ask on a First Date

Engaging in small talk with anyone can be a little nerve-racking — you’re on an improv stage for two, and have to think of things to say on the fly, avoid awkward silences, and come off as at least moderately charming to boot.

Engaging in small talk on a first date can be especially anxiety-ridden. While unspoken, you’re being actively evaluated on your attractiveness (both in personality and looks). It’s like a “job” interview for the position of potential significant other. Ace it, and it could be the start of a lifelong love affair. Blow it, and you might never see that someone special again.

No pressure, right?

As an aid in being successful at this kind of high-stakes small talk, you can find plenty of lists out there which suggest good questions to ask someone on a first date.

These lists tend to fall into two categories: basic, stock questions (“Where are you from?” “What do you do for fun?”), and more unique, out-there questions (“If you could only bring 3 things with you on a desert island, what would they be?”).

The problem with the first set of questions is that they’re boring; if someone is dating a lot, they get tired of being asked if they like their job and how many siblings they have. The problem with the second set, is that they can seem pretty random — and overly scripted — if you just drop them into conversation.

Fortunately, it doesn’t have to be an either-or equation. There’s a better way to ask first date questions that incorporates both types of them

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