My Favorite Questions to Ask on a First Date

Because of the modern era that we now live in, there are two types of first dates:

1.       You met someone out at a bar, etc./you’ve been set up by a friend AKA you don’t know anything about this person and you have to introduce yourself and go through every boring/awkward/lame question to get to know them better

2.       You met them through a dating app – you have what their bio says and you’ve probably already social media stalked them so when you meet them you most likely already know a lot about them but you have to either play it as you still don’t know anything about them or you’re upfront about what you do already know


Regardless of which of these you may face, you’re going to have to go through some Q&A during your first date to get to know the other person better and see if they may be compatible with you. It’s super important to be open minded and listen carefully to how they respond- answers tell a lot about a person. Instead of asking them the boring questions that may not lead into a full-on conversation, here are some ways to spice up the conversation to get to know your date a little more:

Why did you decide to get into the career that you’re in?

o   Instead of asking what they do for a living, which can quickly end a conversation- asking why they got into what they did can leave it more open ended. While this can go two very different ways, it’ll help you see what the person’s motives are. Are they in the field that they’re in because of the money or are they following their dreams.

What do you do in your spare time?

o   This might be a little boring, but it will get to the route to who they are as a person. Do they work out during their time off? That shows they have motivation and like to stay healthy. Did they say they like to drink and go out? That means they may not the right person if you’re looking for someone to settle down with. While your first date doesn’t always make or break the relationship, it definatly tells a lot about a person and who they most likely will be in a relationship. It’s the first impression- make it count.

If you could go anywhere, where would it be?

o   Are they adventurous? This will most likely lead to some personal story as to why they’d pick that place, which will help you get to know them a little bit more!

What was the worst pick up line you ever got (online or in person)?

o   Such a fun ice breaker and it’s sure to make both of you laugh!

What should I know that I wouldn’t think to ask?

o   This is usually the last question I ask throughout the date. It makes the other person think a little. I always hope that they’ll say something super unique that we can start a conversation about. My go to is that my parents are deaf- something super random about me that some don’t know about, which usually gets a whole conversation going!

Make sure to stay open and optimistic during the first date, because the confidence and willingness to open up about yourself can lead to deeper conversations, laughter, and even spark a connection that may not happen otherwise.

Try to stick with open ended answers to keep the conversation going, and if you feel that the other person is being a little reserved, try to ask a follow up question to get them to share a little more or even try to mention something about yourself that may relate to the conversation. The worst thing that can happen is the conversation dies, but it doesn’t have to.

P.S.- if you did meet the person via Bumble, Tinder, etc. try not to make it too obvious that you already know his whole life after social media stalking him…let him tell you on his own so he doesn’t think you’re crazy :)