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How do I Ask Her Out?

Art by Ariana Nouri

“How do I ask her out” is a question plaguing the mind of may teenage boys who are shy and having a hard time asking out the girl they like. This question was submitted by a 16 year old young man who is wondering exactly that.

Dear Doctor Life Advice,

I am 16 years old and I have liked a certain girl for years. I have never said anything too her. I am too shy to talk to hear but I want to ask her out. I don’t know what to say to her. What do you think I should do?Signed: Shy Young Man

Dear Shy Young Man,

This question is a bit out of my league since I am WAY older than 16. As luck would have it, I have a 17 year old editor who reads my posts, especially those written for teenagers. She tore the first draft version to pieces, and provided a lot of advice that I used in this version.I can not tell from your question if you have ever spoken to this girl at all. When you say “I have never said anything to her,” do you mean you have literally never talked to her, or do you mean you two are friends and you just have never told her that you like her? Since I can not tell, I will address both scenarios:

How to Ask Her Out if You have Never Talked to Her Before

This is a tough scenario. I know you are shy, but if you don’t have any kind of a friendship with her, then you have just got to reach deep within you, find some courage, and walk up to her and start talking with her. A good way that I see teenagers start talking to someone is to find a mutual friend and ask them for help in introducing them in a casual way. You can go out to group lunches or another group activity together, and talk to her casually until you’ve established some sort of an acquaintance. To help you overcome your shyness, think of it this way: you two don’t really know each other, so the fact that you like her is not really based on deep knowledge and understanding of her. It is more like you find her attractive, pretty, funny, etc. In this case, then if you approach her and start talking with her, you may figure out that you do not really like her personality anyway. If you begin getting to know her better in a friendship, and find out that you do actually like her, then you can ask her out. See below for the scenario in which you know the girl you want to ask out.DO NOT go straight for asking her out without any form of acquaintance first! According to my 17 year old adviser, “that’s just creepy.” This used to be common when I was your age, but apparently it’s an absolute social taboo these days. Your are stuck with trying to get to know her first.

How to Ask Her Out if You Two are Already Acquainted or Even Friends

This is actually the tougher scenario! Unfortunately, for those of us in society who are shy, there are no easy scenarios. In this case, it will be easier to ask her out, but there is more at stake if she says no.It will be easier to ask her out because if you two already know each other, then you must have a level of comfort being around her. Especially if you two hang out in the same groups, then you probably run into her often. If that’s the case, just hang out more and more with her during the times that the group gets together. During this time you can gauge her interest in you. If she is very interested in talking with you and pays you attention, then the attraction is probably mutual.  If she prefers to just talk with her friends, and dodges interacting with you, then she’s probably not interested.Once you get a good feel about her interest in you, then one day, catch her alone (which is hard because teenage girls always seem to move in packs), and casually ask her if she would like to go out for lunch or a movie. She will probably say OK, but then may ask to invite other friends. If she does that, then she’s not ready to start dating you, and you’ll know that and will have to wait a while before you ask her out again. Alternatively, she just may say OK, and then you’ve got your date!!Worst case scenario here is if she directly tells you that she does not want to date you. This is what I meant by saying “there is more at stake,” because then it will be awkward to run into each other in your group. This is why you really need to gauge first whether or not you have a chance with her. According to my teenage adviser, the awkwardness can last for a long time, so you want to avoid it if at all possible. However, look around you in High School. People your age date for a while and then break up all the time. The situations get awkward, but everyone seems to survive them and move on, and in general the awkwardness does not become an issue that you can’t handle. You have to believe in yourself and tell yourself that if she goes out with you, that would be great, and if she doesn’t, that will not be the end of the world either.


In short, there is no easy way to overcome shyness and ask someone out. Welcome to the world of dating. You just have to do it! It will help you to think about the worst case scenario and know that it’s not that bad. Even in the case of being turned down, you will have accomplished the monumental task of overcoming your shyness!! Each time you ask someone out, regardless of what the outcome is, you will be more comfortable with the process.Also, NEVER forget your own worth! Shy or not, I bet there are a lot of good qualities about you. If you find it difficult to list off all the ways in which you are amazing, then ask your family and friends to help you. Build up your sense of self-worth and self-esteem to the point that even if you get turned down, you can genuinely say in your head: “her loss,” and move on.Remember, even if turned down, you will come out with more experience, so there is no way for you to lose!

Words to live by:

“I reckon it’s again my turn, to win some or learn some.” Jason MrazBest of luck,

Doctor Life Advice

Sayeh Beheshti, M.D.