Hello, lovebirds! Since Valentine’s Day has arrived, I thought that I, as the self-proclaimed relationship expert that I am, should offer some conversation starters to help stave off those gut-wrenching awkward silences that can spoil just about any date. Whether you’re spending your V Day with a longtime significant other or a stranger that you met off of Tinder, the desire that you feel for everything to go perfectly may cause you to become nervous and, ultimately, blank. Don’t fret, my dears! Cupid (a.k.a. me) is coming to the rescue with twenty questions that will, hopefully, foster a memorable discussion and sparks between your boo and you.
1. What were you absolutely obsessed with as a kid?
2. What’s the first thing that you would like to do once the pandemic is over, and why?
3. Who are your favorite artists right now?
And if you’ve never heard of them, then you should ask them to introduce you. ;)
4. What are you majoring in/planning to major in, and why?
5. What are habits and behaviors that really annoy you?
6. Who is your celebrity crush?
7. What are some items on your bucket list?
Pay attention to their answer; it could be important for future date ideas.
8. What is your favorite movie/TV show?
Similar to question three, if you’ve never heard of the movie or TV show, then you can suggest for them to watch it with you sometime.
9. Tell me about your least favorite teacher you’ve ever had.
10. Do you play any sports or workout?
11. What do you enjoy doing in your free time?
12. What interested you in __ school? Where else did you apply?
13. What did you write your Common App essay about?
This question sounds super nerdy, but I promise that it will actually reveal some really profound information about the person with whom you’re on a date.
14. What is the most embarrassing thing that has ever happened to you?
This question will surely elicit hilarious answers and could also provide potential material for inside jokes and banter.
15. What are your go-to stores to shop for clothes?
16. What is the cheesiest pickup line you’ve ever heard or used on someone?
17. What is your favorite book?
If they don’t have one, then you can follow up with asking them about the last book that they read.
18. What personal achievements are you most proud of?
19. Tell me about the worst date that you’ve ever been on
I hope for your sake that they don’t respond with, “This one.”
20. If you could have three wishes granted, what would they be?
If they’re smart, then one of their wishes will be to go out with you again!
With these twenty conversation starters at your disposal, I hope that you feel relaxed and end up enjoying your time with your date! Just don’t forget to invite me to your wedding.