A
male
age
36-40,
anonymous
writes:I have fallen for a best friend of mine. I don’t know if his feelings are reciprocated, what I do know is that I am walking between the borderline of acting on my feelings and pursuing him as more than a friend or restraining myself altogether and avoiding causing awkwardness between us. He has taken an interest in my interests and more obvious recently than ever. Whatever I am into he always expresses interest in. Not a huge sign, because this could be just him finding common ground for our friendship, but when combined with a few other things—the lines in our friendship begin to blur.He has an account on a streaming service and he has shared his personal account information so I have access to his. He used to never drink, but he tried for the first time with me and a couple friends a few weeks ago. When I apologized for the many hangouts we have had recently where we are constantly either alone or with friends, he told me not to worry he’s trying to go out more. We did dinner alone together and our conversation can go for hours and our eye contact is always mutual—but then it might be a comfort thing for him versus an interest since he feels comfortable around me. The crazy thing is he’s interested in my friends (now his) (none of them apart myself are gay). On one of the nights we went out together, he suggested for the group of friends to go to my place, to which one of our friend’s was equally puzzled by his suggestion, as there was no reason to go there. On a separate occasion he made a comment that he will stay at my place if he ever drinks too much. Once again it could be a comfort thing. We have a group text going with our other two friends, but he’s not as responsive on there as he is directly with me—though I know some people just don’t like to do group texts, so that may not mean anything. He also has shared a lot about his family background with me—I am Latino and he told me a lot about the Latino side of his family side. It seems like knowing that I am openly gay does not bother him at all and he wants to share more about himself. This could be a friendly gesture or this could be more. So ergo this leads me to my problem—is it worth the consequences if I end up being wrong to act upon my feelings or should I sit this one out?I am a bit aware that the only way of knowing interest in anyone is asking them directly, but I also know that if I am wrong about his orientation this could potentially create an awkward situation that might change the dynamic of our friendship in an undesirable way. Or third option—should I wait for more clear signs before reaching a decision of what to do?
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male
reader, anonymous, writes (16 June 2016): Firstly never make a first move when one of your best friends is involved. How often has anyone slept over at a friends assuming it would lead to more intimate relations. With friends it does not happen. Friends know you and they understand you doesn't mean they want to sleep with you. I can sleep in the same bed with my best friend and talk about football all night. He knows i'm gay but will still share a bed with me talking about football. My mind wanders in and out of reality at times thinking about what could happen but talking about sports as we lay in the same bed really reminds me that he is not interested in my balls. That is how it should be with friends.
A
reader, anonymous, writes (1 June 2016): As an experienced gay man, I read your post thoroughly; and I read nothing that indicated he has a romantic-interest in you. It is all within the boundaries of a good friendship. No flirtations have been exchanged, no passes, not one inkling of evidence that he has any physical or romantic interest; beyond being a close friend, and trying to expand his interests. Truly and sincerely demonstrating an open-mind and appreciation for his friendship with you.
Of course being a novice around gay people, he may go a little overboard proving how open-minded he is. Like awkward white people around people of color; when they've had very little exposure to other races.
All too often, straight-men who aren't threatened by their gay friends (or gay people), comfortable in their own skins, and confident in their sexuality; for some odd reason gay men become attracted to this. They see it as some kind of opening.
Spoiler-alert! It isn't! Respect the boundaries! I don't let them tease what they can't please. I don't let them touch what I can't touch. I have boundaries too!
You didn't indicate he is gay, has openly expressed he has gay tendencies, or ever said he was gay-curious. Even more confusing is when other straight people presume men comfortable around gay men are closet-cases. I bristle and fume at these presumptions. Especially when women jump to these conclusions with absolutely no evidence to support these opinions, other than prejudice and insecurity.
You expect it from guys; because men are conditioned to be homophobic by society and culture. Many women have gay friends, but don't want their boyfriends to be anywhere around them. Or feel nervous if they become friends.
A heterosexual is a heterosexual. Not that sometimes straight-men do wonder what it's like, and are curious as to why gay men feel and think as we do? That doesn't mean they share our sexual-attraction. They just try to be tolerant, think beyond our sexual-orientation, and see us as just men. That's what we want, and who we are. Not all of us are a woman trapped in a man's body. We are not all effeminate, and we are not all indiscriminately attracted to men no matter what they look like.
Keep your romantic feelings in check, in order to preserve a very special friendship. Don't create awkwardness in the place of his affection for you. He likes you; but don't take advantage of the closeness to turn it into something convenient for yourself. That is an opportunistic posture within a otherwise good friendship; which is rare and wonderful. You have to set boundaries on yourself. Just because you're gay, doesn't mean every man who is kind and friendly to you is a potential boyfriend or bed-partner.
You're mature and experienced enough to know these things.
Keep it in the friend-zone. It's much too convenient to feed on the energy of friendship to make it more than it is intended. Infatuations create tension that usually end really wonderful gay-straight friendships. I have many great straight-male friends, some are even married with kids. They have progressed beyond the ignorance, and we have mutual respect and love, within the appropriate limits of true friendship.
Let him make the first move, then go from there. You don't have enough evidence to express your romantic-feelings for him.
Telling him how you feel won't make him cross-over, if he isn't gay!!! It will only embarrass you, and he may distance himself for all the correct reasons.
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A
female
reader, aunt honesty  +, writes (31 May 2016):
 I think you need to figure out first if he is gay. Therefore try and bring it up in conversation, ask him is he single? Has a gfriend or Bfriend, hopefully will give you a better clue. Or even if you found out the sex of his last partner you would have a better idea. Then proceed to ask him out, on a date. The worst he can say is no and you can carry on with the friendship I am sure, as you are both adults.
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