The Claremont Indecent: 36 questions to ask on a first date

Hey Claremont crushes, long time no see! After a sad, sexless hiatus, I am absolutely horned up to announce that The Claremont Indecent is back and better than ever. So untwist your knickers, and let’s get to it, because I only have more steamy stories to share with you all. 

You may know of the infamous New York Times article, “The 36 Questions That Lead to Love,” but some of us aren’t quite ready to ask, “If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone?” And if we’re ever going to get to that point, we’re probably going to start with a whole lot of first dates. 

Let’s be honest: first dates are terrifying. The only thing scarier than a first date is the awkward silence that is likely to ensue. And in this day and age, it’s often the first time you are meeting someone face-to-face. So maybe it’s the Pomona College overachiever in me, but I’ve learned to come prepared. Without further ado, I bestow upon you a list I sometimes wish I had tattooed on my arm: 36 conversation-starting questions — each one individually tested and proven to start conversation — for fighting the first date fright.

1. How is your day going?
2. What’s been the best/worst part of it so far?
   1. Consider just asking for their rose, bud, thorn right off the bat. 
3. Where do you call home?
4. Who is your best friend?
5. Who makes up your family?
   1. Instead of the overdone “and how’s your relationship with them” or “do you get along” or whatever, I find that you can glean a lot more information by asking:
6. If you and your family were put into the Hunger Games, in what order would you die, and why do you feel this way? 
7. … then to lighten the mood a little: pancakes or waffles?
8. Would you rather have one serving of (insert their answer, pancakes/waffles) OR a drink roulette curse for the next five years?
   1. Explain here that drink roulette entails never getting the beverage you order. But hey, sometimes you get a good deal and good golly wouldn’t life just be a tad more spontaneous and exciting?
9. If you were a cocktail, what cocktail would you be? 
   1. While this question seems harmless and lighthearted, know that it is actually a TEST. Can this person distinguish between this and the question, “what is your favorite cocktail?” Many cannot.Decide how important it is to you that your future potential partner can distinguish between these two things. 
10. An alternative: What type of tree do you most identify with?
11. What’s your favorite type of tree? 
    1. CAREFUL! If No. 10 and No. 11 yield the same answer, you might be dealing with a narcissist. 
    2. If this is too out there for you, consider some more classic what’s-your-favorite’s:
12. Color?
13. Movie?
14. Member of One Direction?
15. Food?
16. Book?
17. President?
    1. (a subtle way to suss out the political views)
18. Musical artist?

1. Animal?
2. Speaking of which, if you could domesticate ANY animal as your pet and lifelong companion, what animal would you choose?
   1. Some factors to consider: can you ride it, cuddliness, habitat necessities.
3. What are you passionate about? 
4. Do you have any secret skills or abilities? 
5. Do you have any hunches about who you were in a past life?
   1. Perhaps this relates to an unexpected skill or ability!
6. What’s your sign?
7. Moon?
8. Rising? 
9. Are you religious?
10. Be honest: do you think that if someone tried to indoctrinate you into a cult, you would be able to resist them? 
11. What’s your greatest strength and weakness?
    1. Because when it comes down to it, how different are first dates and job interviews, really?
12. When and how did your last relationship end?
    1. Intense, but important!
13. Do you read TSL?
    1. If so, don’t you agree that the sex column is undeniably wise, endlessly witty and downright delightful?
       1. Uh oh … are you using these questions too?
14. Quick pivot: How do you feel about Daylight Savings?
15. Have any weird dreams recently?
16. If you could create a restaurant anywhere in the world, where would it be, what cuisine would you serve and what would it look like?
17. If you were a button on the microwave, which button would you be?
    1. Note: Not everyone is popcorn. Feel free to dig deeper here.
18. And last but not least: Should we do this again sometime?

Though I hope I’ve left you with some inspiration, no listicle is going to be the reason a first date leads to lifelong romance or totally flops. Pull these questions out of your back pocket if the going gets rough, but way more importantly: Be yourself. They’d be silly not to want you. 

Much love,

Sleepless on Sixth Street