Okay, so I saw this thing online about “questions to ask on a third date,” and I thought, “Why not?” I’m always up for trying new things, especially when it comes to dating. It can be a jungle out there!
First, I grabbed my notebook – you know, the one I use for all my random life experiments. I jotted down the title, just to make it official. Then, I hit up the internet, searching for some lists of third-date questions. I found a bunch, some pretty generic, some kinda…out there.

I decided to pick and choose the questions that felt the most “me.” I mean, I wasn’t going to ask someone about their five-year plan on a third date – that’s way too intense! I wanted questions that were fun, a little flirty, and could actually lead to a good conversation.
My Actual Third Date Experiment
So, I had this third date lined up with this guy, Mark. We’d had two pretty good dates already – good conversation, some laughs, decent chemistry. I was curious to see if we could take it a little deeper, without getting too serious too fast.
I didn’t want to whip out my notebook at the dinner table, obviously. That would be super weird. Instead, I memorized a few of the questions I liked. My strategy was to weave them into the conversation naturally, you know, see how they flowed.
- One of the questions I picked was, “What’s something you’re really passionate about right now?” It seemed like a good way to learn more about his interests without being too direct. Turns out, he’s super into urban gardening! Who knew? We ended up talking about that for a good 20 minutes.
- Another one I tried was, “What’s a place you’ve always dreamed of traveling to?” This one sparked a whole conversation about travel, different cultures, and even some funny travel mishaps we’d both had.
- I also threw in a slightly riskier one: “What’s something that makes you laugh uncontrollably?” I figured it was a good way to gauge his sense of humor and see if it matched mine. He told me this story about his dog getting into a bag of flour…I was cracking up!
The whole thing felt way more natural than I expected. It wasn’t like an interrogation at all. The questions just helped to keep the conversation flowing and gave us some new things to talk about. We learned some new things about each other, shared some laughs, and generally had a really good time.
So, my verdict on the “questions to ask on a third date” experiment? Definitely a win! I think it’s a good way to move beyond the surface-level stuff and get to know someone a little better, in a fun and organic way. I’m not saying it’s a magic formula for finding “the one,” but it definitely made for a more interesting and engaging date. I’d totally recommend giving it a try!