We’ve all been on first dates that feel eerily similar to job interviews. The questions are predictable: what do you do? How many people are in your family? Do you want kids? Where do you see yourself in five years? Cue: snooze button.
While it’s not inappropriate to want answers to these questions — after all, it would be pretty weird if you went out with someone and didn’t find out how they spent their days — there are other ways to find out about someone without making it feel like they’re being vetted for a new job. (Even though that’s kind of what dating is all about, really.)
Asking your date basic biographical questions is a given. However, here’s some thoughtful questions to use as a follow up or in lieu of the usual, “so what do you do?”
- What inspires you?
I always feel awkward asking or being asked, “what kind of stuff do you like to do?” Whenever I encounter that question it’s like my mind goes blank and all I can think of is a boring answer (like, “um, I go to the gym?”) that does little to highlight the fact that I’m actually an interesting, well-rounded person. Ask your date what inspires them. You might be pleasantly surprised what they have to say.
- You have the chance to design your dream concert. Which headliners would you choose?
Like many people, I’m a major audiophile, yet (like above) whenever someone asks me what kind of music I’m into I usually draw a blank and just end up telling them “The Roots?” (If my date happens to have no idea who The Roots are, this is when things officially get awkward). As a courtesy to my date, I like to ask this instead. It’s always interesting to hear what people say. Besides, even if my date has different taste, I still want to be with someone who is as obsessed with music as I am. This question says so much more than simply asking someone, “so, do you like music?”
- What do like most about your job?
Instead of asking someone about their career plans, ask them what they like best about their job. Not only does it give you information on who they are as a person and what they do for work, it also lets you know whether they’re actually happy in their career. (Personally speaking, I want a partner that’s happy doing what they’re doing or at the very least, working towards a career that makes them happy.)
- What did you want to be when you grew up?
Like the question above, this question gives valuable insight into someone’s personality and what makes them tick. It can also provide a great moment of comic relief. For example, when I was a kid I wanted to be a ballet dancer/lawyer/actress/writer/Nancy Drew, because realistic #lifegoals.
- What’s the strangest job you’ve ever had?
I love this question for the same reasons mentioned above. This is a chance for your date to wax poetic about that time he worked as an iguana breeder while also providing an opportunity for you to bond over the fact that you were both employed at a sewage treatment plant the summer after freshman year of college. Really, you can’t go wrong.
- Where’s the best place you’ve ever been and where would you like to travel most?
I’d much rather hear about someone’s wanderlust, than the ins and outs of their career trajectory. Asking someone about their travel plans is a great way to indirectly tease out their general lifestyle and values. Are they an all-inclusive resort kind of person or do they prefer backpacking through Tibet? Where was the last place they traveled? Did they have a good time? Their answers are sure to be more interesting than making awkward small talk about their job in data processing.
When it comes down to it, it’s not even so much what you ask but how you ask. If you’re going to ask someone what they do for a living (a totally normal question), don’t do this:
You: “What do you do?”
Date: “I’m an iguana groomer.”
You: “Oh, cool. Seen any good movies lately?”
Instead, make sure you’re following up with more open-ended questions that can’t be answered by one word answers. For example, this would be a great time to ask question #3, #4 or #5. Instead of thinking of the date as an interview, see it as an opportunity to get your date talking and see where the conversation goes.
