20 Questions to Ask Your Crush



Questions to Ask Your Crush

These questions will require you to muster up the courage to actually go talk to your crush and to ask these flirty questions. Asking your crush basically anything is a good start, so included in the list below are some safe conversation starting questions as well as some more direct flirty questions that will for sure let him know you are interested.

1Who was your first kiss?

This is a question that brings up that “first love” feeling, and with you sitting in front of him while he is feeling this “first love” feeling can’t be bad. It is just a flirty question that could come with an incredibly cute or incredibly embarrassing story. Be prepared to answer these question for yourself if you decide to ask him.

2Are you a relationship man or a loving the single life kind of guy?

This lets him know you want to know! You can play it off all cool like his is just a fun question, but you both know where this question is coming from. If he answers “loving the single life” you know he probably isn’t interested.

3Can I have your number?

Come on ladies, get it together and stop being shy! Just go ask for his number, guys do it all the time. It isn’t that hard. It seems terrifying when you think about it, but just imagine how sexy, hot, confident he will think you are when you walk up to him and ask for his number! He won’t be able to say no.

4Where is your favorite place to eat?

“I’ve never been, you will have to take me sometime.” You see what I did there? I think this probably only works if you are already friends or at least talk to your crush on a regular basis. If this isn’t you just mix up the question a little and turn it into a conversation starter. “Where is a good place to eat in town, I am so burnt out on pizza and chinese take out?”

5Is there any movies coming out soon you want to see?

“Me too! We should go see it together.” If going with you alone seems a little much, say a few of your friends want to go, turn it into a group thing. My freshman year of college at least 10 people went to see a Marvel superhero movie just so two of our friends could go on kind of a date and hang out. Group anything with your friends is always great, so even if he doesn’t ask you out on a one-on-one date you will still walk away with an awesome night spent with friends.

6What is your favorite bar in town?


This is similar to the last question, if you feel comfortable saying, “Hit me up next time you go, it sounds like a fun place,” by all means do it. But if not mix it up again, “Me and a group of friends were looking for a new place to go this weekend, and I knew you have lived here for a few years and might know of somewhere cool.” Make what you ask fit your conversation and your personality. The last thing you want to do is be someone you aren’t.

7Can you help me with ______________?

Homework, figuring out this coffee pot, getting a book off the top shelf, my car isn’t starting, etc. If you need help with something and your crush is around, go ask your crush! People ask each other for help all the time. It isn’t an out-of-the-blue, random, awkward question. It is a great way to start forming a friendly relationship with your crush that can potentially turn into something more.

8What do you do in your freetime?

I don’t know if i would specifically ask the question this way, because it kind of sounds like a job interview. But, if you find out that they play tennis on the weekends and you play tennis too, try to bring it up in conversation. Common interests have long been the foundation for relationships, just saying.

9Do you like chocolate chip cookies?

Because, I have some extra? Do you want them? If you work together this is perfect! At past jobs my coworkers brought food and baked goods to the office all the time, and it was usually the best days at work ever. You could start by bringing cookies for everyone and if he likes them, just bring him a few occasionally when you make them. It will be subtle friendly gesture if he isn’t interested, but if he is he will pick up on your hint.

10Are you listening to _____________?

He has music playing in his office or low at his desk and you know what he is listening too, don’t be afraid to say “I love this song!” or “did you know they are coming to town for a concert in a few months.” Again, common interests.

11What is your major?

If you go to college you know this questions seems to be the most commonly asked question of all time. It’s not weird to ask a stranger you just met what their major is. You’ve spoken three words to the girl who sits next to you and the next thing you know you are now discussing each other’s majors. It’s got to be the weirdest thing about college. It’s like we are all secretly categorizing everyone based on this fact alone.

12Do you know where ____________ is?

Again, on college campuses this is great! If you are new at work this could be a conversation starter too.

13Iphone or Android?

“I’ve been thinking about getting a new phone but I’m just not sure what I want. What do you have?” Everyone that has a phone has a preference about what kind of phone is the best. This could be a great talking point if he seems a little nerdy or techy.

14So I heard our professor moved the test is that right?

The only time I talk to people I don’t know in college is when I don’t know when something is due, then the person who sits next to me is my BFF. This is a great reason for adding someone on Instagram or Facebook too, I couldn’t even begin to count the number of times I have Facebook stalked someone in my class just so I could message them to see if the test was infact tomorrow.

15Do you know when we are having the company picnic this year?

Simple questions related to work or school are great talking points because they don’t seem out of the ordinary or random. They are a great place for a friendly relationship to begin.

16Did you get the email our professor/boss sent?

Again, a number of times the professor has sent out an email that failed to reach me and I hear someone else across the classroom talking about how an assignment was moved or class was canceled next Thursday. Even if you did get the email say you didn’t, great reason to talk to your crush.

17Do you want to join our study group?

Our parents and probably even our grandparents used “studying” as an excuse to hang out with someone. It’s code for “hey, I like you and now I have a reason to hang out with you.” One-on-one study sessions are your safest bet. But, if you are scared of getting turned down use the study group for an excuse to hang out. Just make sure you have a study group beforehand. Beware though, one of my friends in college invited a girl to study with him and another guy in an attempt to eventually ask her out… she fell for his friend. Ouch!

18What is your type of girl?

Like the first kiss question this is just a good thought process for him to take while you are sitting in front of him. He will describe someone similar to you if he is interested or someone completely opposite if he’s not. Plain and simple that is how it works. Again though, this question might only be acceptable if you already have a friendly relationship with him.

19Are you single?

Just ask!!! (see question three, “Can i have your number?”)

20Where are you going to take me when you ask me out?

Just go for it girl! Be confident and use a somewhat cheesey pickup line if you have too. Be fearless. He may turn you down, but then you know he’s not interested and you can move on.



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