7 Questions You Wouldn't Think To Ask On A First Date But Should

By Gwen Farrell
·  5 min read
7 Meaningful Questions To Ask On A First Date To Get Insightful Feedback

We’ve all been there: rapid heartbeat, sweaty palms, nervous fidgeting. There’s not a whole lot that’s as anxiety-inducing — or exhilarating — as a first date.

Physical attraction is a key component of mutual interest, yes, but that only goes so far. What’s really a good litmus test for genuine attraction and true compatibility is conversation.

It’s not uncommon to go on a first date and feel awkward or vulnerable, or even that the conversation was stunted and wasn’t as productive or as interesting as it had the potential to be. We need to be having better conversations, and that all starts with asking better questions

So here are seven meaningful (and telling) questions to ask your date:

1. What do you do in your spare time?

Having a job is great, and what someone does for a living says a lot. But what they do with their free time says even more. If they like to relax and take it easy, great. If watching TV and sleeping in is all they do, though, they might not be excited about waking up early on a weekend to go for a bike ride or a trip to the farmer’s market.

Actively pursuing other interests outside of their comfort zone indicates a commitment to personal development.

Additionally, actively pursuing other interests, projects, and activities outside of their comfort zone or their 9-5 job shows a person who’s committed to personal development and to trying new things.

2. What makes you nostalgic?

Asking someone to fully delve into their childhood on a first date is, admittedly, a bit much. But asking what they’re fond of reminiscing about or what memories they treasure is a more efficient way of doing so. And it allows you to find out what they really appreciate and keep close to their heart.

3. Who are the special people in your life?

If a person has a great relationship with their family, they’ll have no problem discussing it. But there are many people who don’t, and this question can gauge who the maternal, paternal, or sibling figures are in their lives.

If a person has a great relationship with their family, they’ll have no problem discussing it.

Observing how someone talks about other people also provides good insight into the influences they’ve allowed to shape them as a person, and potentially, how they’d even treat you if the relationship develops.

4. What’s a chore you hate doing?

Anyone can wax poetic about the things they love; it’s relatively easy. But watching someone talk about what they don’t like is just as interesting, especially if it’s the mundane or annoying things like unloading the dishwasher or taking out the trash. Speaking from personal experience, asking someone how they feel about doing things they don’t like doing is a good indicator of how supportive and generous a partner they’ll turn out to be.

5. What’s the best present you’ve ever received?

Personally, I’m not a fan of overly materialistic personalities. It’s great to have nice things, and I like them just as much as the next person. But a person who noticeably emphasizes their income, zip code, car, etc., might not be a good match (if you’re like me). If the best gift they’ve ever received is a Rolex watch or a luxury car, think about what that choice says about them.

If the best gift they’ve ever received is a Rolex watch, think about what that choice says about them.

If they paid for it themselves from hard work and dedication, that’s different, but when there are so many other possibilities out there, it makes you start to wonder what they’d try to save first if the house caught on fire. 

6. What does a normal day look like for you?

This question is one with vast, untapped potential, one from which even more questions — and therefore continued, deeper conversation — can arise. A person talking about their average day can naturally progress to what they do for a living, hobbies they enjoy, the food they like, the people they hang out with, and so much more.

7. What’s your biggest pet peeve in a significant other?

Asking about exes on a first date can open a whole can of worms that’s not necessarily welcome or appropriate for the setting. But it’s insightful to see how a date (and maybe a potential significant other) indirectly talks about past partners.

It’s insightful to see how a date (and maybe a potential significant other) indirectly talks about past partners.

Asking a date about their pet peeves is such a common question on many first dates. But asking about character flaws or personality traits they dislike in others is a great gauge for what they might find insightful and attractive about you, and what naturally draws them to romantic relationships.

Closing Thoughts

Whether they’re an extrovert with great social skills or an introvert with a tougher shell to crack, these are interesting questions that are out of the norm and typically unexpected, which can take your conversation from dull to sparkling.

Looking at an attractive person across the dinner table is nice, sure, but deep, insightful answers to uncommon questions can reveal a lot about a person — first and foremost, if there’s a need for a second date.

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