First Date Questions You Should Ask

So: The profile caught your attention and the e-chat was so awesome you made a real-world date.

And before you lay eyes on each other for the first time—in person, I mean—you’ll have spent time imagining and hoping that he/she is exactly what you’ve imaginedand hoped they’d be. The subjective Q&As expire quickly (“You like sports?”, “You like books?”, whatever), and will likely have been exhausted before you even meet.

Time to get grounded.

If you’re at all serious about an ongoing relationship, there’s some essential gotta-know info that could sway your decision making. You’ll wanna sneak these questions in somewhere along the way. They can make for and awkward date, but once the first is on the table, hopefully the ice’ll crack.

“Where do you work?” Chances are you will have already asked “What kind of work do you do?”, but “where?” is a completely different story. If you ask this early during the date, it’ll sound like small-talk. If you save it, you’ll have a better context for the answer. What you’re looking for is this: is your date an unemployed deadbeat?

“Are you married?” People (often—mostly—guys) lie about this. They’ll either expect you’re taking for granted they’re not married, or, if asked, will expect you to believe the lie. Ask again, face-to-face. If need be, chase it with a “Really?”. Watch for The Blush of Guilt.

“Have you ever been married?” I think it’s fair to know if there’s an ex in the background (feel free to resort to the “Really?”-chaser again). If so, dig for drama. There may even be kids in the package. Which leads me to…

“Do you have kids?” If so, does your date seem like a loving parent, or does it strike you that kids are a nuisance to their lifestyle? The answers not only reflect character, but can be a red flag if kids are/aren’t in your cards… even for a weekend.

“You’ve never been arrested, have you…?” I have no problem asking this. The answer is likely (and, for me, has always been) no, and you can have a good laugh. It opens the floodgates to awesome conversation… especially if the answer is yes…

Now the controversial part:

Since the dawn of “civilized society”, there’s this silly notion that we must avoid discussing politics, religion, and sexuality.

Bullshit, I say. Confront anything and everything “THEY” tell you to avoid. Investigate the politics, religion, and sexuality of anyone who interests you. First, those issues (if they exist) are defining; second, they can come back to bite you in the ass.

Good luck, Sherlock!

Find your next first date at!

Ready to Find Local Hookups?

Explore the Best Hookup Sites for Getting Laid in 2022.

Find Hookups Now

Tell us what you think

Notify of
Inline Feedbacks
View all comments