Congratulations! You’ve agreed to go out on a first date because something about this guy has won you over to say, YES. Now it’s time to prepare yourself, so you can get past all the fluff and get a true sense of his personality on the first date.

Here are 5 questions to pop in throughout the conversation with your date to determine if you’re compatible and whether a second date should even be in the forecast.

First Date Questions

5 Questions To Ask On The First Date

Q1. What’s your favorite way of spending an evening during your work week?

Discovering what he enjoys doing after he’s clocked out gives you a sense of his lifestyle. Maybe he enjoys bowling or having a few drinks at the bar. Depending on his job, he may just find it more relaxing to hang out at home and watch TV. This question will help you determine if you both have similar lifestyles.

Q2. What kind of magazines or online magazines do you enjoy reading?

This question has dual benefits. First, it gives you the opportunity to learn about his interests and gives you insight into what kinds of things he likes to learn about. Does he read business magazines, entertainment magazines, or magazines related to his hobbies? The second benefit is this question usually opens the door to other conversations.

Q3. Are you passionate about what you do for a living?

This question should not be answered with a simple yes or no. Ideally, his answer will give you a glimpse into whether or not he is satisfied with his career. Let’s say he isn’t thrilled with his 9-5. Is he ambitious enough to change it? He may not be fulfilled, but his answer may indicate he’s using his current career path as a stepping stone toward something else. You’ll get to see if he’s ambitious, a dreamer, and/or a guy who works on getting exactly what he wants.

Q4. What makes you laugh?

Good-humored individuals are seen as more attractive, according to research. Finding out what makes him laugh is a good way to get a sense for his style of humor. Everyone’s sense of humor is different. Does he like to hear jokes or tell jokes? Is he able to find the funny side of things in life? He may be more of a teaser, someone who gets a kick out of the suffering of others. Pay attention throughout the date as well. You’ll start to notice what amuses him.

Q5. What is something that you’ve done lately that you’re proud of? 

Maybe he’s learned a word in another language, met a new fitness goal, or read an interesting book. Hearing about something that he’s proud of allows you to see what he values in life.

First Date Bonus Tip

Here’s one last word to the wise… Don’t let your first date be an interrogation. Be sure to interact by sharing stories and your own answers to these questions.