You finally matched with someone. You even got along with them over text before asking them out on a date. You managed to put together an outfit that makes you feel confident. But maybe your social anxiety is making your head spin, maybe you are lousy at first impressions, or maybe you forget how to act like a person when you get nervous. Either way, here are a few things to help get over the awkwardness of first dates and first date conversations. 

First things first. It’s okay to say that you are nervous. It’s a first date. They are probably just as nervous as you are. It might help relieve some pressure you are both feeling. Who knows, you might even get a laugh out of it. 

The Basics 

You probably talked to the person you’re on a date with over text for at least a few days to see if you guys are even remotely compatible. But if you didn’t already cover the basics, here is a shortlist of questions you could ask them.

Basic Questions for First Date Conversations

  1. Where did you grow up? 
  2. What’s your family like?
  3. Do you have any siblings?
  4. What do you do for work? 
  5. Where’d you go/are going to school?

Family and our childhoods are part of the reason we are who we are today, so getting a glimpse into what their family is like and their childhood is always a good start. For some, this topic can be touchy, or they aren’t completely comfortable with opening up about it quite yet, so make sure you aren’t pushy. Just be patient and move on to something else. 

Personality Questions 

These kinds of questions let you get to know the other person. What do they like or dislike? What kind of adventures have they had in their life? This part is fun because it lets you know what the person is really like and if you’ll mesh together in the future. 

Personality Questions for First Date Conversations

  1. What’s your favorite place in the entire world? 
  2. What’s on your bucket list? 
  3. What’s the scariest thing you’ve ever done? 
  4. What’s something you could talk about endlessly? 
  5. What makes you laugh the most? 
  6. Do you cook? If so, what’s your signature dish?
  7. What’s your favorite movie, tv-show, and book? (If they like to read) 
  8. What are your friends like? 

Honestly, this is a vibe check. If you’re going to date someone, then you have to be somewhat compatible. You have to be able to match energies. If you are a homebody, then maybe dating someone who needs to be out and about at all times might not be the best for you. (That’s for you to decide.) Or maybe you’re an adventurous person who likes to try new things and be spontaneous, and the person on your date is all about habits and order and making plans in advance. I know the cliche saying “opposites attract,” but you need to make sure that your opposites aren’t going to annoy each other to no end. 

What-If Questions 

These are personally my favorite kind of questions. The 5th grader in me likes to hear how people respond to what-if questions. They could ask something crazy and imaginative to something boring and mundane, but they help you better understand the person you’re on a date with or they do for me. 

What-If Questions for First Date Conversations

  1. If you could choose one house chore to never do again, what would it be and why? (We all have that one chore we absolutely hate, and seeing grown adults moan about things like that is almost always funny.)  
  2. If you could plan the perfect day, what would it consist of for you? 
  3. If you had superpowers, what would they be and why? (This is my favorite question. I probably ask every single person I meet this question at some point.) 
  4. If you could live in any fictional world, what would it be? 
  5. If you could live anywhere in the world, where would it be? 

I live in the what-if world in my head. I love thinking about the crazy hypotheticals that kind of just pop into my head. It might be from all the fantasy books I read as a kid, but I love these kinds of questions because I am a pretty imaginative person who can talk for hours about the differences between a grilled cheese and a melt or how a Founding Father would react to the world today. And for me, I need someone crazy enough to indulge the dumb questions I have in my head. It’s all about finding someone who can match your levels of crazy, goofy, and weird. 

At the end of the day, asking questions is important, but they don’t mean anything if you aren’t listening to the answers. You don’t want to ask questions like it’s an interview, and you’re just going through the bullet points. It’s a date. Have fun, listen, crack a joke or two, and be present. You might be surprised at how far being a good listener can get you. 

Check out these additional tips to having a solid first date.

1 Comment

  1. […] And when you have overthought all of that, you can start to overthink about all of the stuff you will talk about on your first date. But it’s okay cause we have you covered. So here are some things to keep in mind for first-date conversations.  […]

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