It goes without saying that first dates are awkward enough without knowingly putting your foot in your mouth. By asking crazy questions that will make your date feel like he/she made the worse mistake of their lives by going out with you, is something you can definitely avoid. Here are 20 Questions you should never ask on a first date

1. You seem great, so why are you single

Asking this question insinuates there is something wrong with being single. If you’re on a date with someone who you know is amazing rather than ask why they are single, simply be grateful.

2. What dating apps are you on?

This question serves no relevant purpose and may come off as an accusation. It is not helpful or polite about making conversation.

3. You’re not crazy, are you?

Followed by “I’ve been meeting a lot of crazy people lately”, you may come off as strange rather than cute. It is best to focus on questions that let you learn more about your date.

4. Where do you see this relationship going?

It’s the first date chill girl! This is a weighty question to ask and may cause you’re a date to feel pressured. Asking this may also cause you to look desperate and foolish. You may seem to be rushing things on just the first date.

5. How much did that cost?

You’ve got to be kidding, you didn’t ask that did you? Regardless of what it is, car, house, luxurious bag, it is none of your business. Asking makes you appear tacky and shallow and only concerned with money. It is better to compliment without asking for the price. Even when you’re in a relationship and have separate finances. You should never feel obligated to tell your partner the price of something you spend you’re own money on.

20 Questions you should Never ask on a First Date

6. Are you seeing someone else? 

At this point, also to weighty! This question implies a more intimate question “Are you having sex with anyone else? The first date is too soon to be asking intimate questions and will come off as intrusive and a bit crazy.

7. Do you like my outfit?

Or any other question related to your appearance. They have loaded questions and you may not like the responses. We are not about to get our feelings hurt and then throw a tantrum

8. Do you want to have kids?

And will we home school then? Yeah exactly, a little too out there. First dates should be for getting to know each other on a lighter note. These questions should be asked later down the road like date 5 or 6.

9. What are your deal breakers?

Do you even know your own deal breakers? Asking this may seem to be saving you some time but may come off as counterproductive. It may appear that you are trying to find their likes/dislikes so you can pretend to like/dislike them or decide whether you are interested in them at all.

10. How is your relationship with your parents?

This may be intrusive and make them uncomfortable. It may even get worse if they aren’t on good terms with their parents or their parents died. People would assume that because you do not have a good relationship with your parents you have “mummy and daddy issues”. We all have a little to be honest.

11. What are you?

A SPACE ALIEN! If you are using this to ask about a person’s race or ethnicity then don’t. If someone wants you to know about their race or religion, then they’ll let you know. It’s racist and offensive hands down.

12. What do you want to do tonight?

So you haven’t thought one ONE thing to do on this date, are you even interested in the least? Asking this may make you seem unprepared and is uninterested in your first date.

13. Do you drink a lot? Cause I do.

You probably don’t drink as much as you think and making a comment like this while just getting to know the person will come off badly. This should be reserved for when you get to know each other better.

14. Why did your last relationship end?

Don’t ever ask about previous relationships especially the dynamics of their divorce. It’s really none of your business and asking about the details of a bad past relationship might make the person feel uncomfortable.

15. What are you looking for in a relationship? 

This is another topic that should be saved for later in the relationship. It puts a lot of pressure on the other person and makes it easier to walk away if things don’t work out. Asking can make it sound as if you are trying to find out in hopes of playing the part of what they want.

20 Questions you should Never ask on a First Date
20 Questions you should Never ask on a First Date

16. How many people have you slept with?


This question is extremely inappropriate and personal and is none of your business. It is impolite to expect them to reveal the answer to a complete strange that they might never see again!! NOPE!

17. Do you own your house?

You might think you’re subtly gauging their financial situation, you are actually being rude. Trying to figure out how much your date has in the bank on the first date is never a good idea.

18. What’s your favourite sex position? 

Again, really! If you are looking to never have a second date this is a good way to do it. It’s pretty much impossible to ask that without being a jerk.

19. Do you always eat/drink like this?

No matter the reason, anyone who asks there is now winning with this question and it is an immediate red flag. They should be avoided at all costs.

20. Tell me About yourself?

This is an overwhelming statement that can cause an awkward pause. Rather than asking that question, opening up is a good way to move topics along and get to know each other

The first date is just the get to know you phase, you really just want to see how comfortable you are with the person. You know to see if they eat with their mouths open or smell like old socks. Take this opportunity to enjoy their company and be happy to be out and about and not worry too much about getting to the hard issues.

When you get to a real solid relationship, here are some great date night ideas that will absolutely love! Enter name and email to get your checklist.