Some of y’all may remember me from the dating burnout post that a lot of people had very valuable and helpful comments so back again!

I have two dates lined up this week and I wanted to come back to ask what are your top first date questions to evaluate if someone’s emotionally available and ready to date. Mainly, I would want to determine if they have an avoidant attachment style or are just looking to put on a mask to play games to get what they want (usually sex or temporarily emotional intimacy) and then disappear.

There are obvious ones like talking trash about multiple ex’s or never taking accountability but I know you all have some gems that I have never thought of. I will drop two in exchange that I like to ask that tells me a lot if someone is happy with their life and if they have the mentality that will vibe with mine.

1. What is something that gives you child like joy? How often do to get to do this thing? This tells me they have something that makes them genuinely happy outside of going out to bars or vacations or whatever the cliché answers are for “what do you like to do for fun”. Also, if they do it on the regular, it shows me that they prioritize their own happiness.

2. What was the last thing you heard on a podcast, heard from a friend, or read in book that’s stuck with you? This shows me that personal growth is important this person, and they are open to receiving new ideas that are not just their own perspective.

* my intention is not to interview someone, it is trying to ask deeper questions past the typical- What do you do for work, how was your day, or other superficial stuff. It gets old. A lot of it is how you approach these questions and tone. Not trying to give someone the third degree whatsoever.

34 comments
  1. Someone recently asked me “What gets you passionate and animated?” and I hated it.

    I want someone that I can just be with, not someone where I am going to feel pressure to constantly impress.

    I guess “personal growth” is not as important to me.

  2. Lol I’m not going to interview people to date. You just have to learn how to listen to your gut and remember the things you learned. How are you supposed to spot a liar by asking him these kinds of things? It would be easy to pretend to be anyone in the first few stages of dating. You have to accept the fact that sometimes you’ll be disappointed and that’s just that. No amount of interview questions will keep that from happening.

  3. The best questions are those that get the other person to relax and be themselves, lower the mask so to speak, but I am still trying to work out what they are.

  4. I feel almost as if questions like the ones you posed are very much interview-like questions, like I’m being vetted for an office that is quirky and has a pool table and lounge space. They don’t feel organic, it’s not how you actually talk to people.

    You learn these things about people as you get to know them, and there’s no quick hack to doing that – it comes with time.

  5. lately I ask more simple questions about daily routine like what time did you wake up this morning? hahahah only if it kinda works in the conversation tho … then you can talk about like if ur morning or night owls, if it’s changed over the years…

  6. > Mainly, I would want to determine if they have an avoidant attachment style or are just looking to put on a mask to play games to get what they want (usually sex or temporarily emotional intimacy) and then disappear.

    Asking what they learned from their last relationship and how they respond can tell you their level emotionally availability if they talk more about the person vs the experience they learned.

  7. 1) Just ask what they like to do for fun and go from there. It’s a much more common question that essentially asks the same thing. The childlike joy version can result in answers that aren’t actually an activity they do. They might say, “colorful sunsets give me childlike joy.”

    2) This really sounds like a job interview question. I think it would make for a great job interview question, not a great question though to ask a date you barely know, unless maybe the right situation comes up.

    Avoidants are not always easy to spot either. My ex-husband broke up with me in a way that was textbook avoidant, and has been acting like an avoidant ever since (I handled the breakup with a textbook anxious attachment style). There were some things that in hindsight, were avoidant behaviors throughout our relationship, but there was no way I could have known he was like this when we met. These kinds of people can cause horrible amounts of hurt to others, but unfortunately, they can be hard to suss out until you get to know them pretty well.

  8. hear me out here: how do you feel about kids/marriage?

    it sucks to find this out later on and it’s incompatible with what YOU want.

  9. This comes off like a job interview and could be off putting to people. There is no way you can know of someone’s flaws or attachment style on one date. You just have to get to know people and keep getting to know them until you decide if it’s worth continuing or not. There is a phrase “date ‘‘em till you hate em” while I understand it would be nice to quickly weed out people it’s not that simple all the time. People naturally put their best foot forward to be liked and that’s why you have to keep getting to know them to figure out if it works or not. You can weed people out for very apparent red flags or incompatibility but I wouldn’t approach things with questions like this. Instead focus on just trying to get to know them and seeing how the conversation plays out and if there is any chemistry or banter or vibes.

  10. The best first date questions to ask are the ones that flow logically/organically from what you’re talking about and show awareness and insight in to the topic at hand, demonstrate an understanding of context, and have a light/fun tone/outcome.

  11. Something fun I like to ask anyone is “If you could have three people over for dinner, who would they be?”

    Could be cartoon characters, historical figures, anyone..

    A good follow up is “what would you make for dinner?”

  12. I personally enjoy asking what’s something that made you smile/laugh recently? And if they can’t think of anything I give them a super cheesy dad joke like what do you call a sad strawberry? (A blueberry) or what do you call a bear with no teeth? (A gummy bear)

  13. I stole this from someone else on here, but I like the question, “What gets you out of bed on Saturday mornings?”

  14. I just get the basics done. Nothing fancy. “What do you like to do for fun? How do you like to unwind after work? How do you like to spend time with a partner. What are you looking for?”

    And I also look to see what he asks me. Is it important? Is it small talk fluff? Is he focused on trying to impress me? Is he assessing me?

    Because I want to see he’s looking for something real too.

  15. I feel like going into a date with preset questions you’re treating it much like an interview and already setting it up to not flow naturally. I think most people freeze up when unexpectedly being put on the spot like that, I know I do. I have a ton of things that bring me child like joy but if I was asked unpromted I’d forget every single one. Try just relaxing and going in with no expectations and just seeing where the date takes you as far as conversation and vibe.

  16. “What would your friends warn me about” is my third date question if things are going well.

  17. Can I just say I appreciate these questions? I know the mass majority is saying it sounds like an interview but I disagree. It’s important to find someone with their own hobbies and own identify.

  18. What’s your favorite cheese?

    Do you prefer cow, sheep, goat, or buffalo milk cheese?

    Would you accept $1 million if it meant you can never eat cheese again?

    Let’s say we wanted to run away together and start a dairy farm. Tell me about our farm and where it is

  19. What’s your biggest trauma and how do you think it impacted your view on life or changed you? I like to cut to the hard stuff lol

  20. The purpose statement “evaluate if someone’s emotionally available and ready to date” should contain “ready to date me in the way I want to be dated by this person.”

    I don’t think you can have access to that information on a first date. Meyers Briggs, attachment quizzes, horoscopes and hogwarts schools are all great gateways to self-knowledge and conversation starter. But I tend to think our predictive powers of whom we will be in a new relationship is poor. The Venn diagram of sets of “compelling first date” and “good long term partner” may not overlap much.

    I just like to get people’s life stories as they understand it. Family, hopes, dreams, favorite books, preferred pizza toppings. Actually, in the vein of a good interview question with no bearing on relationship fitness, I always ask about someone’s favorite meal they have ever eaten. It’s a window into their aesthetic appreciation of the world.

  21. Look up Adam Lane’s Smith three-date method.

    Your first date should be focused on primal connection and conversational flow and connection (FORD – Family, Occupataion, Recreation, Dream), but the last half of the date, definitely be clear about your intentions and expectation.

    Your talk of expectations will turn off avoidants… and that is exactly the outcome that you want, no?

  22. I actually really like your questions, though they may be difficult to think up answers to on the spot.

  23. If you asked me these questions unprompted, worded as you stated, I would 100% recognize they were sourced from somewhere with the intent to solicit information and would be weirded out.

  24. Honestly I’m done with questions, people can say anything, behaviour and most importantly my instinct doesn’t lie.

  25. I like to ask “what would be your dream job?” If the answer is super unrealistic, like any type of professional athlete or celebrity, I know this person is a bit immature and may not prioritize planning for the future / having a family. Whereas if it’s something more realistic but aspirational, and they explain their thought process, now I know this person’s long term goals.

    A similar one I’ve asked and been asked is “what would you do if you won the lottery?” You can kinda tell people’s money habits with this one. I’m a frugal person, so when I think about winning the lottery, I imagine I’ll live pretty similarly to how I live now, but maybe work less lol. Look for responsibly fun answers. 🙂

  26. I remember I went on a date with a guy that when there was a lull in conversation he whipped out his notes app and started asking me personal question. It was a bit of a turn off. In a way I was flattered he thought about all these things to ask me but it felt too intense. I didn’t see him again after that.

  27. Ask them questions that got you interested in them originally – link to their profile and ask about that.

  28. I don’t agree with previous comments.

    Timing and presentation affect how you ask questions on a first date. And, there’s not real “organic”/”natural” flow. That’s just bad preparation. Of course, you shojld steer a date towards topics you want to hear more about.

    Assuming you’re on a coffee date, it probably runs 60-90 minutes.

    Timing:
    I wouldn’t start with those types of deeper questions. Rather, if you think the initial part of the date is going well and you both feel comfortable, then and only then, would I take it to a deeper level of discussion.

    Presentation:
    These deeper questions, I don’t pose as a question per se. Rather, I ease them into it. And, the key here is for you to be vulnerable first, which would help them open up to. This is a classical tactic for deep human interaction and to deepen the relationship – regardless of if its plutonic or romantic.

    Example, 1:
    “So I was at an afterwork with some colleagues, and someone brought up a really interesting question. She asked x, and some answered y and my take was z. What are your thoughts on the topic?”

    Examples, 2:
    “So I’ve been reading a book/OpEd/topic recently, that is about X. I’ve been digging into it lately with friends and would be curious to hear your thoughts on it too. My opinion on it is Z, some friends said Y, What is your take?

    At times, when the date is going well or it’s too plutonic. I might shake things up and bluntly say: “Hey, how about we leave the superficial things aside and go into some more personal or deeper topics, would you be up for it” No girl ever said no. Again, key is for you to be vulnerable first, them second. Always answer the question you ask first. That’ll make them feel comfortable.

    Good luck! Would be curious to hear how it goes!

  29. OP, it was 6 days ago that you posted about being burnt out on dating. You’ve also posted about being burnt out with your job. It sounds like you are going through some weightloss things too. Stop trying to force things with these unhinged questions and work on yourself. My god.

  30. I think these questions are great. I like to get deep early and anyone here saying they ‘don’t want to be interviewed probably doesn’t have the emotional intelligence to understand what you’re going for. As a sensitive man with a high EQ I would be absolutely buzzing if a women asked me these questions just in general not to mention on a date.

    These questions are great filter criteria to find the emotionally available person you’re looking for. Just remember, there are less of us than there are of those that think they are but haven’t actually done the work. So most people aren’t going to like these kinds of questions, but that doesn’t mean you shouldn’t ask them. Just because some is 30+ doesn’t mean they’ve grown up yet.

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