Okay, so I decided to get back into the dating scene. It’s been a while, and honestly, first dates always make me a little nervous. What do you even talk about? I didn’t want to end up in one of those awkward silence situations, so I did some digging beforehand. I wanted to figure out some good questions to ask – you know, stuff that goes beyond the usual “what do you do?” and “where did you grow up?”.

I started by jotting down some general categories. Like, I wanted to get a sense of their personality, their passions, and what they’re looking for in life, also include in a relationship. I figured those were good starting points.
My Question-Gathering Process
- First, I brainstormed. I literally just sat down with a notebook and wrote down any question that popped into my head, no matter how silly it seemed.
- Then, I went online. I read some articles and blog posts about good first date questions. I wasn’t looking for cheesy pickup lines, but more like genuine conversation starters.
- I also thought about past dates – the good ones and the bad ones. What questions led to interesting conversations? What questions fell flat?
- I refined my list.I group similar questions with same *, I removed some questions that are too personal or too boring for a first date.
After all that, I actually practiced saying some of the questions out loud. Sounds a bit weird, I know, but I wanted to make sure they sounded natural and not like I was reading from a script.
I sorted out those questions into serveral group, such as “breaking ice” group, “know more about hobbies” group, etc.
The date itself? It went pretty well! I used a few of the questions I’d prepared, and they actually sparked some really interesting conversations. We talked about everything from our favorite travel destinations to our most embarrassing childhood memories.I used questions from “breaking ice” group at the begining, make us feel relax.

Then, I used some from “know more about hobbies”.
One question that worked really well was, “What’s something you’re passionate about right now?” It led to a whole discussion about his interest in photography, and I learned that I also had some interest on it.
I definitely felt more prepared and confident going into the date, and I think it made a big difference. It wasn’t just about having a list of questions; it was about being genuinely curious and wanting to get to know the other person.
At the end of date, I felt I have known much more about him that I used to be.