Top 15 Questions I’ve Asked to Vet People on Dates

Em Win
Mar 8, 2024
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Pictures of the Autostraddle senior editor team are collaged in colors of cobalt and orange with the words "Happy Birthday Autostraddle" and the number 15 strewed all over for Autostraddle's 15th birthday

Autostraddle is turning 15 this week! To celebrate, we’re publishing chaotic and gay Top 15 Lists all week long.

Ranking the actual questions I’ve asked on dates wasn’t very difficult. No, the challenging part was remembering all the extremely odd things I’ve said over the past 10 years of dating people.

I’ve realized it’s not so much the questions themselves — but the secret test behind the questions that I’m somehow expecting this random person to ace.

15. Can I see your tattoos?

This is a good intro question and not totally out-of-pocket, but the intent behind it is to get closer to my date – as in – I’m hoping this gets physical soon. This is purely for sexual chemistry.

14. What is that?

Generic, yes, but this is in direct reference to whatever random niche thing my date is into, because it’s always something I have never heard of before! The area of interest can tell you something about what fills their mind daily, which can reveal a deal breaker. I’m not sure I’ve ever actually dated anyone with the same extremely specific fixation as me.

13. What are your feelings about Disney?

This is more nuanced than just looking out for people who love Disney or people who hate it, but someone who is reasonably skeptical and is also down to watch a movie occasionally and go to Disney. I work at Disney and let me tell you: there is truly a fine line between a fun, nostalgic time and a lifestyle.

12. Do you have any weddings coming up?

This is not a move to get a plus-one invite! I want to know how someone feels about weddings and marriage. Are you offering critical commentary? Are you gushing about your friends in love? Did you forget that your best friend is getting married next month (major red flag for me)?

11. How do you feel about living in Florida?

Again, the extreme answers are a significant indicator of someone’s general life outlook and phase of life. Are you completely ignoring the politics and realities of living in such a conservative state (why am I even on this date?)? Do you hate this place and aren’t doing anything about it to make yourself happier? Or, do you recognize how you can love your community and work towards making it better?

10. What if I told you I like Taylor Swift?

I’m a bit ashamed of this, but it’s the honest truth. I could never be with a Swiftie hater. At best, I can deal with indifference.

9. Are you a “go with the flow” type of person?

I can’t stand this phrase!! I’ve been jaded by the number of people who’ve written off my feelings by saying, “Idk, I’m just going with the flow.” If you’re relaxed and laid back but still care about this relationship, say that. Don’t gaslight me! Take initiative! Feel your feelings!

8. What are you watching right now (but what I really mean is, are you obsessed with The Office)?

Listen! It’s cool if it’s your thing, but the people I know who like The Office straight up make it their personality. I can’t deal with this in a romantic or sexual situation. Other warning signs include exclusively watching old episodes of Friends or not being open to anything new, ever.

7. Wait, you listen to the Joe Rogan podcast?

WHY?! And why am I on a date with you?

(*I still slept with this person and went on many dates after that.)

6. Are you familiar with Enneagram?

Unfortunately, my own red flag is that I love personality tests and tools! I cannot tell you how often I’ve used this question to determine people’s motivations, behaviors, and relationship patterns. It’s like the therapeutic alternative to asking someone’s star sign. I can gather an infinite amount of information about how they argue, what they are like when they’re stressed, what makes them happy, or what shuts them down without actually asking them directly..

5. What medications are you on?

Hopefully, I’ve asked this after we’ve had an appropriate conversation about mental health struggles, and they’ve clued me into their health situation. Sometimes, it just comes out. Please do not ask this on dates.

4. Picture yourself lying on your deathbed and fill in the blank. “I’m so happy I _______.”

This question aims to understand what is most meaningful in a person’s life. My friends and co-workers are used to getting questions like this, so I had no idea it was not normal. I didn’t realize this was such a jarring question to ask until people started looking at me like a deer in headlights.

3. Are you crying?

I realize this sounds judgemental, but it’s more of a clarifying question. I’ve been known to make people cry on first or second dates. I’m not trying to upset them in any way, but I love asking my dates deep questions and sometimes I tend to get into their own traumas without even realizing it. I’m studying to become a therapist, so this makes sense.

2. Do you have friends?

I try not to ask this question so bluntly, but it’s imperative to understand what the person’s support person looks like. What I’m screening for here is the likelihood of codependency and their ability to keep and sustain relationships.

And yes, I also realize that, when not handled with care, this question is absolutely out of pocket, but I wouldn’t know to ask it had I not had previous unfavorable experiences.

1. I just stare at them until they say something.

I’m incredibly comfortable with intimate silence, so this tactic usually draws out a more realistic response from someone.

Some people get awkward, others get a little insecure, and people stare back. In this last scenario, it’s usually a flirtatious stare, so I know I’m in. However, the possibility of this doesn’t negate the fact that staring at someone is my top question.


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Em Win

Originally from Toledo, Ohio, Em now lives in Los Angeles where she does many odd jobs in addition to writing. When she’s not sending 7-minute voice messages to friends and family, she enjoys swimming, yoga, candle-making, tarot, drag, and talking about the Enneagram.

Em Win has written 84 articles for us.

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