125 Questions to Ask Him

Cut Through the Awkwardness and Uncover His True Self

The first few dates were a whirlwind — good food, witty banter, those butterflies that mean you might just be crushing hard. But now, you’re starting to wonder… is there more to this guy than his charming smile and perfectly timed jokes? Sure, you know he’s a software developer who loves sci-fi and has a weakness for cheesy puns… but who is he really?

Generic small talk isn’t cutting it you’re craving deeper connection, to find out what makes him tick, his hopes, dreams, the slightly strange quirks that make him uniquely him. You want to know if your values align, if you can picture a future together. But let’s be honest, the usual “What’s your favorite color?” questions won’t get you far.

Plus honestly, I just hate dull, lifeless, vapid conversation. I can not be the only one.

A dull dates make you question everything. Is he just not that into me? Am I not that into him? Or are we simply stuck in a rut of superficial conversations, afraid to truly open up?

Imagine this instead: a date full of laughter, unexpected revelations, and moments where you think, “Wow, I didn’t know that about you!” Imagine discovering shared dreams, or playful disagreements…