15 Great First Date Questions That Guarantee You Won’t Have A Boring Night

Making conversation on a first date can be hard. We get it. But there’s one question you should absolutely despise and avoid at all costs: “Why are you single?”

There’s really no winning answer and a terrible first date question.

Depending on who’s asking, almost every response can put you into one of two boxes. You’re either bitter and lonely, or you’re out here “hoe-ing it up.” Even the classic response, “I haven’t found the right guy/girl yet,” can sound cliché, corny or, frankly, unbelievable.

And then there’s the unintended consequence: The question can send you spiraling back to the person who got away or dredge up negative feelings from past relationships. Who wants to spend a first date talking about their ex, or defending why they don’t currently have a partner?

There has to be a better way.

With cuffing season approaching, our writers at Cassius decided to ask friends, both IRL and on social media, what they actually wanted to be asked on a first date. The responses were plentiful, but one thing became clear: A successful first date isn’t necessarily about determining whether there will be a second date, or whether you’re going to hook up.

It’s about creating a vibe.

Did the conversation flow? Did you laugh? Did you learn something? Did you get a little deeper than small talk? Most importantly, did you enjoy being present with the person sitting across from you?

With that in mind, we put together a list of questions that can help keep the conversation moving without making your date feel like they’re sitting through a rapid-fire job interview. Whether you’re looking for a relationship, a second date or simply a good time with someone interesting, these questions can help you learn more about the person without killing the vibe.