Do you guys have a formula or series of questions that you ask on a first date? I was chatting to a friend who is also single about going speed dating recently and he said he was worried that he wouldn’t have enough time to get all the info he normally gleans on a first date. Now obviously speed dating isn’t a real first date anyway, just an introduction. But I was wondering if I should be more intentional with my conversations on first dates in future.

I do bring up my nephew as a way to spark the conversation on kids without out and out asking if they want children. And I ask if they like travel, dogs etc. But usually for me a first date is just to see if we’re attracted to each other and we could have fun together. The problem is that for me attraction is often a slow burn and I love meeting new people so I almost always have fun on a first date! I find it really hard to tell if I enjoyed the person or just having a chat and a drink.

So, yeah. Do you guys have specific questions or conversations that you want to have on a first date to help you understand the person and your compatibility. If so what are they?

8 comments
  1. I’m childfree by choice and quite politically active so I generally will bring those things up as they are dealbreakers for me. I recommend making a paper list of your very basic dealbreakers and thinking about 1) how to subtly communicate those things in your dating profile and 2) how much of a problem these things would be for you vs whether you are dating casually vs for a long-term commitment

  2. I’m just trying to have a good time and learn a little about them. I can ask the hard questions later

  3. How’s yur momma an’ dem?

    Sorry, a little redneck leaked out there.

    My first date questions always include dealbreakers, childhood, family, hobbies, future professional goals, future personal goals, and I like to use fun hypotheticals (i.e. If you could have a superpower, if you were a transformer, 3 books or movies on a deserted island, etc).

    Also, keep the questions open ended. Yes or no questions don’t lead to conversations and story telling.

  4. Every date I’ve (38F) gone on they wanted to commiserate pretty early about the dating experience during Covid. That’s usually when I reveal my deep secret.

    …I am so awkward that I compiled a 9 page list of questions that start as small talk and get progressively more probing if their answers seem to call for it. Guys have all thought it was hilarious and wanted to see it. I just tell myself that they’re probably as nervous as me and it takes the pressure off.

    I start with stuff like best and worst place you traveled, worst date you’ve been on (this will tell you a ton), do you have siblings and what are they like, did you grow up here or move here and why, have you ever been on TV and why.

    Then fun things like what exhibit do you go to first at the zoo (this one sparks so many interesting conversations), if you were a street preacher what would you yell about, favorite type of jelly.

    If things are going well I’ll dip into pages 8-9 that have the deep ones like happiest days of your life, who did you vote for in your first election as an adult, do you think money can buy happiness, etc.

  5. I used to. But not anymore. I’ve met some people who have a list of questions and wanted to make sure that I check all the boxes. You know what… we’re not shopping for a car. I try to see a person as a human being. I want to see the big picture. The image of the person as a whole. Specifications are for materials, not humans. But sometimes in dating people forget that they are dealing with human beings…

  6. “What would you do with a million dollars?”

    That one right there is very telling of their financial thought process while keeping it open ended and an easy going light hearted question.

  7. I would like to know more about their lifestyles. I’m ready to settle down in my city. I’m looking for the same.

    I have a car and I normally drive to the date. I would say something like “it’s easy(hard) to find parking there” if the guy say “I don’t have a car, and I don’t need a car. I would just get a Uber or rent a car when I need” that’s a no for me.

    I am saving to buying a property. I would say something like “the housing market here is getting crazy” if they say “yeah, it’s impossible to buy a house here, I would just rent” or “my friends just moved to X city, it’s very affordable. I think I will move to that place in a few years” that’s a no for me.

    I am ready to invest time in a relationship. I would ask them “how’s your week?” If they say “I did this with friend A on day B, and that with friend C and D on day E, and this and that with friends FG…” it’s nice to have some hobbies and friends, but if your schedule is already busy with your friends/ activities/ family, I think you enjoy your bachelor life well, and don’t feel the need for a relationship or maybe don’t have time for one.

  8. One of my favorites…
    “What is the worst *true* thing your ex could tell me about you if asked?”

Leave a Reply
You May Also Like