How Do I Ask My Best Friend Out?

I’ve had a crush on my best guy friend for years. I want to ask him out, or even get him to ask me out but I just found out that he likes someone else. How do I ask my best friend out? If he says no, how do I keep it from being awkward?

First, I’m going to give you my best suggestion. Then I’m going to answer your question since I know it’s going to be difficult to follow this advice. It usually comes in hindsight.

My best suggestion is to keep him as a friend and get to know him a little better and move on to other men who have more interest in you.

Here’s Why:

If you are crushing on him intensely and thinking that you guys would be “good together”, you may be eliminating other prospects in your mind and you are less likely to flirt with guys that find you attractive.

Your crush on your best friend does little for your self esteem because you are probably wondering why he hasn’t made a move. Are you pretty enough? Are you his type?

If he had a strong interest, he would have made a move some time ago. He may be shy, but with men, they usually find some way to show you their interest. It may be helpful to observe the way he acts around this girl “he likes”. Pay attention to what he does. Does he make moves? Does he talk about how he is going to call her? Does he go on dates with her?

Is this what you want for yourself? Do you want a man to make moves and pursue you? Then it probably won’t be in this relationship because he has already had his opportunity to “view” you and contemplate the idea of a relationship with you and has decided against it, especially since you say he likes another girl.

If you want that pursuing feeling you will have to flirt with other men. You don’t want to get stuck in a “friendlaship” (I made this word up:) – It’s a friendship/relationship that goes NOWHERE. And you end up getting hurt when your friend gets into a relationship with someone else.

I’m going to also challenge you to really get to know your friend. What does this mean? Chances are if you have a crush on him you’re only focusing on the “good” things about him. But what you will need to do is to get into some real conversations with him and find out about him. Write down a list of what you want in a relationship. Is this really the guy that is going to be able to provide that for you? Look at it in an objective way.

I’ve been there, I’ve had a crush on a friend. BUT, as I got to really know him and not covering up all his “faults” with rosy glasses, I realized that the WORST possible thing that could have happened to me was us getting together, he’s an awesome guy, that’s why we’re still friends but honestly we would not have worked for a variety of reasons.

But to answer your question, I would say you definitely will want to know whether he likes you or not so you can stop expending mental space on thoughts of a relationship if there is no chance.

My best advice is actually from an interview I did with Marvin Barrett on “Signs that A Man Likes You”. He mentioned a pretty cool way you can determine a friend’s feelings for you. Mention to your friend that you had a “weird dream” and give a little background. The background info should be interesting or revealing in some way. Maybe you guys kissed, had children or got married. Tell him that the weirdest part of it was when you woke up it felt so real. Follow this up with “Could you imagine if that were true?”  Wait for his response. His answer is going to be very telling of his feelings about you.