Should I let these things hold me back?

I'm falling in love with my friend. There are two problems.

(1) There are plenty of signs that he's got feelings for me, too, but there are also some signs he is gay. However, there are just as many other signs that he isn't. He's preppy and dresses well. He's artsy and likes theater, which some people think only gay men are into. When my siblings met him they got the first impression that he was gay. He has only had one girlfriend and doesn't date or sleep around since their breakup over three years ago, but he's such a good-looking and charismatic guy that he should be getting tons of dates. A gay friend of mine says attractive men not dating around is a sign of being gay, but I've also heard plenty of straight men say they don't date because it's such a hassle and they enjoy their freedom. The guy in question says he's just not into any of the girls who've shown interest in him.

(2) The real problem is that our mutual best friend doesn't want me to date him. Six months ago I told her I have very strong feelings for him and she said she wouldn't be comfortable with us dating, so I decided to just try to stay friends with him. This week I asked her about it again because, despite trying to see him as just a friend, I've slowly been falling in love with him. I asked her to be more specific this time about her objection. She said she's worried about what would happen if he and I ever broke up. I guess she would have to choose sides, and I'm actually worried she would take his side since she's known him longer. However, he's such an amazing person and I've never felt this way before, so I'm willing to risk both friendships to be with him.

He told me he's too jaded to ask a girl out unless she tells him she likes him, so he knows for sure she won't reject him. My question is: I've gotten to the point where I want to tell him how I feel so I can see if he feels the same way. Should I let these things hold me back, or should I go for it?

- Or - should I wait until he tells me how he feels so I can be sure he's just as crazy about me?


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Have an opinion?

What Guys Said 1

  • I don't think that he'll tell you how he feels from the way you're describing him. I don't think that he is gay though. Just because someone isn't dating and they are good-looking doesn't mean that theyre gay. Several of my friends could get a lot of girls but they prefer not to date for the same reasons and its not that theyre scared either, they constantly flirt and talk to girls they have just met but they never want a relationship -- at least not now. If you tell him that you like him and he doesn't feel the same way though, from the way that you are describing it, it might not seem like anything is different but, he will certainly not think of your relationship the same way

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What Girls Said 1

  • I'm going to assume your very young.. like 18...

    1... if your really really good friends.. why not just ask him if he is gay? A. he says he isn't and you have a good laugh about it.. B. he admits he is gay.. you both have a laugh about it and you get over him C. he says he's confused ... well this just means he needs time and there is no one who can help him decide what his sexual preference is.. except for himself... you can easily stereotype someones behaviour and preferences ... but just because he likes theatre doesn't mean he is gay and just because a girl listens to tegan and sara means she is a lesbian. just ask and you will find out! I'm not saying just blurt out "are you gay?" ... try something like... "oh my god.. I heard a rumour the other day that so and so said you were gay!? isn't that funny?" - cue his reaction/response...

    2. I think your other good mutual friend as an ulterior motive.. ie she may be into him as well. if she was a really good friend she would try her best to work something out between the two of you if things turn sour. why do you have to ask her permission anyway? its your life and your the one who is falling for him.. would it make a difference if you didn't have this mutual friend? you are all adults... if things don't go well (assuming he isn't gay) then you will work it out... and if your friendship doesn't last through a break up then find a friend who is willing to stick with you through thick and thin!...

    dont wait for someone to come to you.. its easier for you to do something... so just tell him how you feel.. just make sure that other mutual friend isn't close by.. :D

    all the best!

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