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

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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 has written 73 articles for us.

7 Comments

  1. Please don’t compare use of the relatively common if slightly annoying phrase “go with the flow” to gaslighting, a tactic of ongoing emotional abuse intended to profoundly destabilise a person’s sense of self and understanding of reality

  2. “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”

    wow, sounds kinda stressful for your dates?

  3. I love this! These are questions that can really get into who someone is, what their life experience has been, and what they value. I can feel the quirky and genuine motivation – and the vulnerability – in them.

    I understand the point of question #9 about “going with the flow”, but I have a totally different definition of that phrase. It’s more of a spiritual relation to the world – definitely not an excuse to be disrespectful and noncommittal. And while you mentioned that the reason #3 made sense was because you’re training to be a therapist, I thought that made #1 even more hilarious because it sounded so much like therapy (or a stereotype of therapy) to me!

    Anyway, thank you for sharing! I enjoyed your questions very much and I hope you find – or have already found – someone who finds you completely delightful!

  4. This article really rubbed me the wrong way. Specifically, questions 1, 2, 3, 5. From some of your questions (and explanations) It sounds like your dates are experiments and you don’t really think about (or worse, care) what impact your questions or actions might have on the person sitting across from you. People can cry because their boundaries are being crossed and people with trauma can sometimes not realise when they’ve over stepped their own boundaries (by disclosing personal information too quickly) or when someone else has (by not noticing signs of someone’s discomfort or reluctance to answer or speak further on a subject). I speak from personal experience.

  5. I totally realize the fun and light-heartedness of this article and I appreciate you sharing :)

    I did want to pushback on question 2 just a little…so I am one of those queers who actually doesn’t have a ton of friends. And not for lack of trying! I am extroverted and outgoing, and frequently am putting myself out there to meet new people (and I promise I’m not a terrible person either!). I know how to make friends, it comes naturally to me. However, in this stage of my life, I just haven’t had much luck. People I’ve tried to form close relationships with have either been way too busy to add new friends into their lives, just had a baby, just recently moved, too introverted to hang regularly, not enough interests in common, etc. So just because someone doesn’t have a super robust friend group doesn’t mean that they are some codependent loser who can’t sustain relationships.

    My biggest fear with dating is people jumping from “oh, this person doesn’t have a ton of friends” to “therefore, this person is a codependent mess, huge red flag, and something is wrong with them”. And sure, I’m sure as you mentioned, that not having a ton of friends can indeed lead to codependency, not denying that either. But I do hope that if someone were to ask me question 2 and I answered honestly that they wouldn’t immediately write me off.

    All that said, I enjoyed the list, and thanks for sharing!

  6. I’m confused, why would not having friends be a sign of codependency? Shouldn’t it be a sign of independence and of being comfortable with being alone?

    Also to anyone reading this who is friendless and feeling doomed by a feedback cycle of people rejecting you for not having friends. You are worthy of love, and there are plenty of people who don’t rely on social proof when deciding who to date/befriend.

  7. “I’m studying to become a therapist, so this makes sense.”

    Scariest-in-context sentence I’ve seen on here in a while, both in itself and as a late-blooming bi person who’s new to queer dating after a long, formative and abusive relationship. I’m autistic and have a hard time with the idea that dating will require me to spot red flags while the other person is perhaps seeing stuff about me and my differences as a red flag.

    It just adds to my sense that dating is this weird artificial situation people set up as much to catch each other out as to look for chemistry. Maybe this list is meant to satirise this problem?

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