How can I [18F] ask my best friend [19M] of 8 years out?

r/

So, I [18F] and in love with my best friend [19M]. He’s smart, attractive, empathetic, and one of my greatest people in my life. Now, recently I thought that he was dating someone else. You can find me freaking out about it in my profile. Anyway, he ended up telling me that he wasn’t dating her or anybody else. Knowing this, I want to ask him out. But, how do I do that without freaking out? I’ve never dated anyone, let alone been on a date with a guy. I’m scared that I’m going to mess up over my words and make him uncomfortable. We’ve been friends for so long, and a few of our mutual friends think we should go out with each other. I agree, but I’m not sure if I should approach him about it.

Since we’ve been friends so for so long, I’m worried that our friendship will change for the worse if I told my truths. I can’t really ask my family about it because they’re close to his family. So I told them, they would definitely tell his parents, and it would go back to him.

Comments

  1. sparklekitteh Avatar

    My best friend in college asked me out, even though he had no idea if I liked him, and neither of us had ever dated before. 22 years later, we’re still very happily married!

    Get brave and go for it!

  2. Monarc73 Avatar

    “Hey. How would you feel if you and I went out on a DateDate?”

    This makes your intent clear, while also preventing anyone from feeling too pressured.

    Good luck.

  3. bluegrassgazer Avatar

    Just be yourself when you ask him out and be prepared for an awkward moment where he might not reciprocate. If that happens, tell him his friendship means very much to you and you won’t approach the subject again. Those kinds of friendships can be very special and they sometimes, but not always, bloom into other things. I ruined a friendship because I kept bringing up the possibility every year or two and it became just too much. I really, really hope you get a pleasant surprise from this! Good luck!

  4. thenakesingularity10 Avatar

    Life is about taking chances. If you never take chances you’ll never get anywhere.

    Go for it!

  5. takhallus666 Avatar

    Dooo eeet. Seriously, you miss 100% of the shots you don’t take. Worst case, things will be awkward for a while, but you will be able to move on. Best case, he feels the same way, but is also afraid of messing up your friendship.

    Somewhere in between, he’s totally clueless, and this will pop on a lightbulb in his brain.

  6. Glass-Image-4721 Avatar

    “Hey, I’m kinda in love with you, do you wanna date?”

    Look, I know it’s nervewrecking, but pretty much all of my male friends have historically had a crush on me back — like 10 to 20 of them, with the exception of one who turned out to be secretly gay. Some of them wouldn’t mention it for like five or six years after we had become friends because they were scared. Turns out most men only befriend women they’re at least somewhat attracted to, and the friendship over the years only increases the attraction. 

    You have great chances of him reciprocating those feelings.  

  7. Entire_Sun_1982 Avatar

    Just come out with it, or you’ll always wonder and if you’ve been friends for that long then you will find it just as comfortable and of course it’s going to change your friendship but that could be a good thing! I say go for it worst case he says no and you can still be friends

  8. white-spider_lily Avatar

    I couldn’t wait until the weekend to tell him how I felt. I called him and we ended up going out to the park and there I told him about the photo and everything. I did cry, which made me feel even worse. But he just hugged me and I told him that I’ve always liked him. Then I said I loved him. He smiled and hugged me tighter. He kissed me (my first kiss!) and walked be back home. I am so happy! We’re now officially dating!

  9. 3portie Avatar

    Try not to worry about trying not to make things uncomfortable. Things will probably feel uncomfortable that’s okay you’re not going to die.

    If the thought of rejection would be harder for you to deal with than asking then do not ask.Also, do you see signs that he is interested in you? If you do not then asking him out could be a reach but maybe it won’t be. Also be prepared to possibly lose a friend if you are not able to be comfortable around him after a rejection.

  10. Ok-Replacement-2738 Avatar

    So I didn’t ask my BF of 8 years out, but i did tell her how i felt.

    mixed bag, initially really good, then she was avoiding me for the next year, we just went to a show and had blast.

    I told them fulling accepting that yeah it wasn’t going to happen, told them as such, and that I actually didn’t want a romantic relationship. (we’re both dysfunctional people.)

    my mistake was not making it crystal clear that’d i was fully content remaining friends since like the 2nd year?. She avoided me because she felt as if I was pretending and didn’t know how to cope.

    I’d suggest you really need to be fully accepting that it may not amount to anything.