5 First Date Questions to Ask


First dates. They can be super awkward if you let it, but they definitely don’t have to be. 

They’re supposed to be fun and involve lots of talking. You’re trying to get to know this person you just met, but how do you get  to know them without asking questions? What questions will keep the conversation flowing naturally?

Here are 5 questions I like to ask on the first date:

Are you married? Are you divorced? Do you have a girlfriend? Do you have children? Does anyone in your life think they are married to you? Does anyone in your life think they are your girlfriend? Does anyone think they are your child?

Ok.. maybe.. Some of the questions were an exaggeration, but you get my point. I like to be as direct as possible so there isn’t any confusion about their status, what they’re doing, or who they’re with. 

Did you go to college?

I went on a date with a guy on Tinder, and I asked him this question. He was immediately offended. It wasn’t my intention to offend him, but his response answered the question. He was insecure about not going to college and what he brought to the table without a degree. Obvi, there was no second date.

I like to ask this question because you learn so much from their response to it. If the person didn’t go to college, you can learn about what plans they’ve made to be successful without a degree and why they didn’t feel it was necessary to get  one.

If they did go to college, you can learn about their interests, what they learned about themselves in college, if they are using their degree, their work ethic, etc. More than likely, because the world is so small, you’ll probably start to learn different friends that you have in common due to your college connections. 

What do you do? Do you like your job?

Here’s why this is a great question to ask- you get to see if they really enjoy what they do. You find out, are they living in their purpose? Are they doing it because the money is good? Are you happy with what you’re doing every day?

Do you have siblings? 

Here’s why you should ask this one- you’re learning about them and their family. You can learn if they like their family just by their body language and how they respond. Do they hang out? Do they only get together at weddings and funerals? Do they get along with their family? How do they spend time together? Are they even in contact with their family? Do they say things like yeah… I don’t really talk to my brother, etc. 

(real life… this has happened to me before. Why don’t you talk to your brother?!)

What do you do for fun?

This is my favorite question to ask. Why? Because you can see if you have any common hobbies interests! Do they like concerts? Music festivals? Do they like to travel? Are they an aspiring photographer? Do they work out? Are they runner? 

Here’s why this is important- do you want to date someone that is into getting up Thanksgiving morning to watch the Macy’s Thanksgiving Day parade OR do you want to date someone that wants to get up Thanksgiving morning to do the 5K Turkey Trot?

Any questions to keep the conversation going are good questions. I tend to stray away from questions that make it feel like an interview. Those are the ones I hate most. Like what are your goals for the next 5 years? WTF? On a first date? Let’s save that for a different conversation. 

What questions do you like to ask on a first date?

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