Spice Up Your First Date: 25 Cheeky Questions to Ask Him

First dates can be exciting, nerve-wracking, and full of potential. You want to make a connection, but sometimes breaking the ice can be tricky. Asking playful, cheeky questions can help ease the tension and reveal a little more about the guy sitting across from you.

Let’s dive into 25 fun and slightly cheeky questions you can ask on a first date to keep things light, engaging, and revealing.

These questions will give you insight into his personality while keeping the conversation flowing smoothly.

1. “What’s the most ridiculous thing you’ve ever done to impress someone?”

This playful question opens the door for a fun story. Whether he’s tried something bold or quirky, it’ll give you a glimpse of his sense of humor and how far he’ll go to impress someone.

2. “If you could have any superpower, what would it be and why?”

This question adds a touch of fantasy to the conversation and helps you understand what he values most — whether it’s being a hero, having fun, or doing good in the world.

3. “What’s one thing you secretly love that most people would find surprising?”