5 Seemingly Boring First Date Questions That Can Actually Reveal A Lot

by Amanda Bradford

Amanda Bradford is the Founder & CEO of The League, a dating app that combines data and social graphs from both Facebook and LinkedIn to offer privacy from coworkers, more context about a potential match, and a curated community of ambitious singles who desire an equally driven partner.

While you can go online and find a pretty extensive list of questions to ask on a first date, the reality is, it could be quite awkward for most of us to ask things like,"what's the most rebellious thing you've ever done" or "so, what's the last good book you’ve read?" Luckily, if you pay attention to some of the most basic answers to questions like: "how was your day," you can actually learn a lot about a person — even enough to make a quick decision over a one drink date.

The League conducted a survey of over 20,000 users in our community asking “On average, how long in (hours or minutes) are your first dates?” In this survey we found that the average length of a first date is 45-60 mins, or as many described: “a one drink date.” The challenge is having to decide on a second date within a one drink date. If you’re lucky, you’ll Lyft away from an evening with either a “hell yes” or “hell no” mentality, but the reality is that many of us are left in that awkward middle ground without enough information to make a proper decision.

Here are five generic first date questions that'll actually reveal a lot about them:


How Was Your Day?


You can tell a lot about a person based on this unbelievably basic question! If your date responds with ‘it’ and ends with ‘was alright,’ I think it’s safe to cut the date right there. Someone who can’t engage and communicate in a simple exchange is probably not someone you'll want to go out with again. This question is also a good indicator as to whether someone is a positive or not-so-positive person or a ranter-types. And maybe you’re totally into grumpy cats, but those who prefer happy and lighthearted first dates, I suggest sipping on your drink quickly and dipping out ASAP.


Have You been To This Bar Before?


Again, this one will probably come up naturally but is still important! If your date says they frequent the bar you’re at, this is a clue that they are a creature of habit — once they find something they like they stick with it! If their answer is no, this is a big indicator that they are spontaneous and like to try new things! Not only are they going on a first date which takes some guts but they’re also doing it in a spot they’ve never been to. If you’ve ever been on a date with someone and you realize they take all their dates there: NEXT!


What Do You Do For Work?


Career can either be a pain point or a source of pride. Focus less on what their actual job is and more about the way they deliver the answer. I’d prefer a Bartender that has a passion for pouring shots over a totally unmotivated Computer Programmer! That said, there’s nothing wrong with hating your job — we’ve all been there! But if your date is a sourpuss about their 9 to 5, it’s important to ask what hobbies they’re passionate about outside of work. Beware of those who hate their job and have no hobbies and conversely those who are obsessed with what they do and that’s pretty much the only thing they can talk about.


How Long Have You Lived Here?


This question is just about as generic as they come, but can be a window into your date’s social life. If your date says they’ve lived in the area for a while (at least two years), this is a pretty clear indication that they have a solid network of friends in the area. While there is obviously nothing wrong with being new to a place, be mindful that those that are new to the area may tend to use dating apps to meet a ton of new people quickly (aka they’re going on dates every single night of the week to make platonic friendships). Of course, it won't be the case for every newbie, but take note if a date makes a pointed effort of trying to “stay friends” with you even if it seems like you two have nothing in common.


Where Else Would You Consider Living


Out of all the questions on this list, this one is by far the most strategic. Understanding one’s future goals can really help you figure out if your date is here for a good time or here for a long time. And while there is nothing wrong with either, you deserve to know before you finish your first drink. If your date says that they’d consider moving back to their hometown, this shows they’re close with the fam. If your date says they’d like to move somewhere abroad this is a big indicator that they really value new and exciting experiences. Moving is a rather strategic decision for most of us — for instance maybe they’re applying to grad school there or they’re seeking a career in a specific industry (aka moving to San Francisco to work in tech).

If you’re satisfied with your date’s answers to these five totally generic questions that are unbelievably telling, then go ahead and ask them one more: “Should we get another round?”