Taylor Tobin
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Whenever I tell my friends that I have a first date scheduled, the response always includes deep, sympathetic sighs and compassionate grimaces. After all, the “first date” is often riddled with awkward, stilted small talk; to quote the eternal wisdom of “30 Rock”’s Liz Lemon, “Meeting someone new? Ugh. All the nodding and smiling and sibling-listing…”

But maybe it’s time to rethink the “sitting uncomfortably with a stranger, asking bland questions, and barely listening to the answers” model of the first date. Yes, a first date should involve questions...but they don’t need to be basic. Instead, you can use your time to gain genuinely interesting and useful bits of info about your companion, which will help you decide whether there’s a connection to pursue. At the same time, you’ll want to avoid super-personal and in-depth topics, since you’re only just becoming acquainted with this person. That perfect first-date middle ground can be tough to find, but it’s well-worth the effort.

Need a place to start? Try these 15 first-date-specific inquiries, all designed to prompt engaging discussions and reveal intriguing tidbits in a casual, conversational way.

1. Where would you most like to travel?

2. How do you like to spend your free time?

3. If you could only listen to one album for the rest of your life, what would it be?

4. What’s one goal that you’d like to achieve this year?

5. How would your best friend describe you?

6. What’s the best gift you’ve ever received?

7. What would your ideal Saturday look like?

8. Who’s the most interesting person you know?

9. If you had to pick one new skill to learn, what would it be?

10. What’s your favorite thing about living in this town/city?

11. If you won the lottery tomorrow, what’s the first thing you would do with the money?

12. What’s your “guilty pleasure” TV show/movie/activity?

13. Are you a morning person or a night owl?

14. What’s the best meal you’ve ever eaten?

15. What’s your fondest childhood memory?