5 Questions About Their Past To Ask On A First Date That Aren't Uncomfortably Personal

by Korey Lane

Going on a first date is somewhat of a time-honored tradition amongst young adults, as well as one that can end in disaster or triumph. Basically, everyone I know has a story of a first date gone awry, or one that has resulted in a life-long partnership. Either way, first dates are a universally awkward experience, and they can be totally nerve-wracking. If you're wondering which questions about their past to ask on a first date are acceptable, then look no further. There are plenty of hacks for making first dates less uncomfortable, like asking questions to spark conversation.

If you're on a first date and genuinely like the person you're with, you might find yourself starting to daydream about what a future together might look like. Not all first dates are bad, and asking your date about their past can be a great way to discover more about what makes them tick, as well as what they might be looking for in a relationship.

At the same time, it's best to be careful about prying, or making your date uncomfortable — after all, this is only a first date. So, what questions should you consider asking about your date's past? Read on!

"When was your last serious relationship?"

If you're having a good time with your date, it can be a little scary to just ask them about their last serious relationship — but it can also lead to a very revealing conversation.

Asking them when their last relationship was can open up a dialogue about other aspects of their previous serious relationships. This can be very important for you to feel comfortable discussing, especially if you think you might want to pursue a long-term relationship with this person. Additionally, if they do feel uncomfortable discussing their past relationship, that might be a sign that their feelings have been left unresolved.

But remember: Relationships are tricky territory — everyone addresses them differently and has varying levels of comfort when discussing them openly, so tread lightly and with caution.

"What was your most embarrassing moment?"

This question can certainly help to lighten the mood once you're done discussing past relationships. It can lead to swapping silly stories, as well as a chance to bond over being humiliated. Plus, it gives both people an opportunity to be vulnerable in a less-pressurized situation.

"Have you ever been in love?"

OK, this question is obviously a very serious place to take the conversation, but if you feel comfortable opening up to your date and the conversation is flowing, it's one you might consider broaching. It might feel scary to ask, but you could also help to ease your date's mind by answering it yourself. By discussing whether or not they've loved before, you might get a better sense of whether or not they're looking to love again, or for the very first time.

"What were you like in high school?"

While this is definitely another more light-hearted question, their answer can actually reveal a lot about your date — not just about who they once were, but how they saw themselves. Were they super extroverted, with a lot of friends? Did they prefer to eat lunch alone in the library? Either way, keep in mind that people evolve a lot after high school, and that who they were then is not necessarily an indicator of who they are now.

"Have you changed a lot in the past few years?"

This is a wonderfully broad question to ask your date. You're giving them free reign to decide whether to take the question. They can really dive into who they've become, who they once were, and who they might one day hope to be. Sometimes, a general question is best. It allows your date to loosen up and really guide the conversation wherever they choose. Whatever the case, this is a fairly deep question that won't get too personal.

First dates may be scary sometimes, but they are also a great way to learn more about a person, have a few laughs and drinks, and get a sense of whether you and your date click. Remember: A date is grounded in conversation, which is a two way street — not investigation. So, leave your FBI badge at home and take a seat at the table ready to chat, and above all else, listen.