7 Deeper Level Questions to Ask on a First Date


Getting to know someone you might be romantically interested in is not always easy. First dates can be very awkward and just plain phony.

However, if you are looking for more of a long-time commitment, getting to know each other on the first date can give you a glimpse into who this person truly is. The following deeper level first date questions should help you find out whether you are wasting your time or not on your first date.

1. How would your friends describe you?

Asking this question is a good one because it can easily be checked on for validity. You can easily ask their friends how they would describe them, but a truthful answer can easily be detected by your date’s response. Watch their body language to see if they seem genuine.

2. What was your favorite thing to do as a child?

Questions about childhood can be pretty sensitive depending on whether they feel their childhood was good or not, but it does give you a glimpse into how their childhood defined who they are now.

After asking this question, ask why that was their favorite thing to do. Get them to give you details. The more details, the more you find out.

3. How many siblings do you have?

This question is not necessarily a conversation starter, but it can lead to a deeper conversation such as how well they get along with their siblings and what they went through as children. You can find out if there are things in their life that might affect your relationship down the road.

More: 5 Qualities That Make Women Boring in Relationships

4. Are you close to your family?

Here is another touchy subject, but again, it is important because it can affect your future relationship. Remember, “The way he treats his mother defines the way he would treat his future wife?” Do not push answers, but listen openly.

5. Do you love your job?

The answer to this question can give you an indication of what life will be like when they are done for the workday. If they love their job, their life outside of work will be pleasant.

But, if they hate their job, it could be hours of listening to all the misery they have endured. That can be pretty draining.

6. Where do you see yourself in five years?

Okay, it is your first date, not a job interview. However, this is a question that is a good indication of their ambitions for their life. You will be able to determine whether you are a good match with this question.

7. When are you the happiest?

This hard question will get your date to open their heart and let you in. Let them a few minutes to think over the question.

This one is truly challenging. Also, be ready to answer as well to open your own heart.

More: 8 Times You Might Mistake Passion for Flakiness

These questions go deeper than the regular “what do you do for a living” question. They allow you a glimpse into whether or not this person is compatible and whether you’re interested in pursuing a future relationship. What are some other first date questions you can think of?