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Should I hook up with my "straight" best friend?

Jarren.Anthony

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Perhaps you should flip the viewpoint.
Rather than go into NYE open to what you may be able to get,
perhaps go into NYE thinking about what you can give?

Approach it to his benefit. If the opportunity does present, you could simply offer:
Hey, I'm not sure if there's more to it, but if you want to take things further - if you'd like a freebie experiment, I'm open to it.

Perhaps making it about him would be a more genuine act of friendship?
I really like what you said about switching the view point to what I can offer rather than what I can get. I mean obviously there's always a little bit of "selfishness" wanting things to go your way, but I also have to remember that this isn't going to be only my experience, but his experience too.
 

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Dude just put it out there if you guys drunk and he gets curious like he does move in the kiss then reciprocate. when it is time for bed don't wear any underware under your pants take them off and get in ro bed naked. see how he reacts to your nakedness if he really wants to he will take you up on your subliminal messages that you want to go farthere in your relationship of best friends
 

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I really like what you said about switching the view point to what I can offer rather than what I can get. I mean obviously there's always a little bit of "selfishness" wanting things to go your way, but I also have to remember that this isn't going to be only my experience, but his experience too.
It's been so interesting to read you and all comments. As I see it, considering what you've been doing before, kissing and cuddling in bed I think your friend have some interest. If I were you when in bed and cuddling, don't hide your erection and let your hands slowly explore his body more. I'm sure he'll stop you if he doesn't like when you come closer to his cock. If he let you continue into his underwear, OK. If he stops you, it's OK and doesn't have to be awkward at all. If you go slow, he'll have time to stop you if he feels you go to far and you're both OK. It's not the end of the world! I think the only things you'll regret in life is the things you left undone and didn't dare do! Wish you good luck!
 

Joguy07

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My thoughts on your situation go to the friendship because what you’re proposing isn’t only about you. This guy is obviously important to you, and from how you describe your interaction between each other, he likely feels the same and has expressed just that. In your position, I would approach the issue by thinking about whats more important for both of us rather than just myself to find the answer you’re looking for.

Whenever a friend moves away, it’s natural to wonder on some level how the distance will affect the friendship. Consider the possibility that your friend may welcome assurance that the ability for both of you to feel comfortable being yourselves to the extent that you both have shared is a rare and treasured bond that will be missed. If this is true, tell him as much asking for his permission with intent to continue. A good friend will accept this sentiment warmly and you will get a better sense of what’s to come yourself.

You’re the one leaving. He may need reassurance of where he stands, even if it should seem obvious. By making the parting conversation as easy for him as possible through acceptance, he may express the same to you as well, giving you the ability to recap your appreciation of him. Somewhere in there you might add that in the realization of going away, you are reminded that you will be in a different circle of people. In hindsight, you’re complimented that a casual observer or people without your level of comfort may have interpreted an occasional bromance signal between the two of you as of late and your appreciation of mutual sincerity only assures you what a valued friend he truly is as you appreciate you can both enjoy just being yourselves no matter what. Your friendship with him is a lifetime bud and that even if an action in a drunken moment would’ve indicated a bromance moment, it’s all good because the friendship would have easily won out.

This opens the door to answering your question by letting him know your friendship is not changed by distance. It also gives him comfort to confide in you if he happens to be thinking the same thoughts as yourself without possibly making a regretted, awkward move on him. Instead of you risking it, you just set the complete picture with all the answers and gave him permission for the same without that risk to him, and with a promise that it’ll all be okay no matter what. It’s his move now.

At this point, he may ask direct questions. Be respectfully honest with him. You may offer that your bromance comment is born from picking up on alcohol induced mixed signals (seemingly a way a straight guy can claim innocence if called out), with acceptance of him (if it was his way of casually testing your boundaries) and apologizing if you misinterpreted, reminding him that you didn’t react out of respect for him and your friendship. If he directs the conversation more towards your desire, then great. Of course, you have to be prepared to accept that the answer may be that nothing is or will have changed. If that’s the case, it’s still great for you. Knowing that you have built and enjoy this special friendship and didn’t ruin it by challenging his trust, you have protected a great friendship that he has entrusted in you as well that you both can continue to comfortably enjoy and evolve naturally as it should throughout time.

Hopefully my thoughts are accurately communicated. It’s not my opinion to trick anyone into a situation, but to lay things out so both parties can actively participate in the best possible outcome. If I fall short in this post, I hope someone will get my intent and chime in to help out.
 

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Okay so here's the sitch guys...

My best friend (let's call him Adam) has always been giving me confusing signals. We've known each other for 2 years so far and we get along great. Like, really great. Our personalities are completely the same. He's one of the best looking guys I've ever met, but he's straight. There's never been an issue or embarrassment for him that his best friends gay, and I've always loved that about him and his confidence. A jock and a gay guy being best friends can obviously be considered "incompatible" in societies perspective. The thing though is that starting 3 months ago, when we would hang out at his place or mine, and we would start drinking together, his personality almost does a 180. He always get very touchy, he's pulled my face in and kissed me a bunch of times randomly (because he thinks it's funny), he's wiped out his dick a couple times out of now where (soft), he always starts complimenting me on how good looking I am, and then when we finally good to bed, he loves to cuddle with me. (Like, he pulls me in hard) When we lay together though he never gets hard at all or even a chub, so it kind of seems to me he really just likes the comfort of it and connection.

I've never initiated anything myself though and have always just gone along for the ride because I never want him to feel uncomfortable since he identifies as straight. He also says when we're drunk that he'd never do anything like this with anyone else except me because he feels so comfortable around me. When we're sober though, we never talk a peep about it. Like, not one word. Kind of like it never happened in the first place, but then when we drink again together, it's back on.

I'm moving back to LA next month because my lease is up and I'm bored with Palm Springs, so that means I'm not going to be hanging out with him all the time anymore and probably wont be seeing him for a good while unless he comes to LA to hang out. I'm staying with him for my last two nights here in Palm Springs, and then I'm gone.

My main question or thought that I need input on, is if we start drinking, should I go for it and initiate something my last night here? I'm scared as hell to do so and have it go south, but then again I wont be hanging out with him anymore so I wouldn't have to worry about it being awkward afterwards if it does goes bad. But what if it goes good? I've always wanted to hook up with him, like...bad, but I didn't want to lose my best friend here if it didn't go well. I keep going back and forth and I don't have anyone to run it by except the people in our friend group, which I'd never do. But since I know you guys might be able to relate or have some good input to add, I figured I'd try and ask for help here

Thanks guys!
(Please be kind in the comments)
YOLO
 
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Just because he flips it out doesn’t make him gay..does he know you are gay…? If not then let him get to know the gay side of you.. then if he is gay and feels same about you then things will go fine… if not then it’s not to be
 

Raybo Revoy

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Okay so here's the sitch guys...

My best friend (let's call him Adam) has always been giving me confusing signals. We've known each other for 2 years so far and we get along great. Like, really great. Our personalities are completely the same. He's one of the best looking guys I've ever met, but he's straight. There's never been an issue or embarrassment for him that his best friends gay, and I've always loved that about him and his confidence. A jock and a gay guy being best friends can obviously be considered "incompatible" in societies perspective. The thing though is that starting 3 months ago, when we would hang out at his place or mine, and we would start drinking together, his personality almost does a 180. He always get very touchy, he's pulled my face in and kissed me a bunch of times randomly (because he thinks it's funny), he's wiped out his dick a couple times out of now where (soft), he always starts complimenting me on how good looking I am, and then when we finally good to bed, he loves to cuddle with me. (Like, he pulls me in hard) When we lay together though he never gets hard at all or even a chub, so it kind of seems to me he really just likes the comfort of it and connection.

I've never initiated anything myself though and have always just gone along for the ride because I never want him to feel uncomfortable since he identifies as straight. He also says when we're drunk that he'd never do anything like this with anyone else except me because he feels so comfortable around me. When we're sober though, we never talk a peep about it. Like, not one word. Kind of like it never happened in the first place, but then when we drink again together, it's back on.

I'm moving back to LA next month because my lease is up and I'm bored with Palm Springs, so that means I'm not going to be hanging out with him all the time anymore and probably wont be seeing him for a good while unless he comes to LA to hang out. I'm staying with him for my last two nights here in Palm Springs, and then I'm gone.

My main question or thought that I need input on, is if we start drinking, should I go for it and initiate something my last night here? I'm scared as hell to do so and have it go south, but then again I wont be hanging out with him anymore so I wouldn't have to worry about it being awkward afterwards if it does goes bad. But what if it goes good? I've always wanted to hook up with him, like...bad, but I didn't want to lose my best friend here if it didn't go well. I keep going back and forth and I don't have anyone to run it by except the people in our friend group, which I'd never do. But since I know you guys might be able to relate or have some good input to add, I figured I'd try and ask for help here

Thanks guys!
(Please be kind in the comments)
Just ask. Even if you're rejected it would be better than an awkward encounter with even worse results.
 

C4junG0n3_BAD

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Just ask. Even if you're rejected it would be better than an awkward encounter with even worse results.
It has been my experience that persons ask when they want to be mature. Asking also connotes that you are somewhat positive the answer will be yes. That is when everyone is sober , of course. Getting someone drunk or waiting until he or she inebriates themselves is indicative of someone that is about to impose themselves into a perceived unfavorable situation. I've done this. So I do know what I'm saying here.

Alcohol does many things physiologically but the one many rely on is the fact it floods the brain with dopamine. That's why everything is a good idea when inebriated. The brain has no cognitive ability to counter the concept of everything being a good idea. Therefore, we have drunk driving, drunk B&E or robbery, drunk dialing and yes drunk sexual and or physical assault. I speak from experience because I have done all of these while intoxicated.

I had a friend, who has terrified of heights, walk on the top of a balcony enclosure, while inebriated because an idiot dared him. He fell 14 stories. So, there's that.
 

Jarren.Anthony

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My thoughts on your situation go to the friendship because what you’re proposing isn’t only about you. This guy is obviously important to you, and from how you describe your interaction between each other, he likely feels the same and has expressed just that. In your position, I would approach the issue by thinking about whats more important for both of us rather than just myself to find the answer you’re looking for.

Whenever a friend moves away, it’s natural to wonder on some level how the distance will affect the friendship. Consider the possibility that your friend may welcome assurance that the ability for both of you to feel comfortable being yourselves to the extent that you both have shared is a rare and treasured bond that will be missed. If this is true, tell him as much asking for his permission with intent to continue. A good friend will accept this sentiment warmly and you will get a better sense of what’s to come yourself.

You’re the one leaving. He may need reassurance of where he stands, even if it should seem obvious. By making the parting conversation as easy for him as possible through acceptance, he may express the same to you as well, giving you the ability to recap your appreciation of him. Somewhere in there you might add that in the realization of going away, you are reminded that you will be in a different circle of people. In hindsight, you’re complimented that a casual observer or people without your level of comfort may have interpreted an occasional bromance signal between the two of you as of late and your appreciation of mutual sincerity only assures you what a valued friend he truly is as you appreciate you can both enjoy just being yourselves no matter what. Your friendship with him is a lifetime bud and that even if an action in a drunken moment would’ve indicated a bromance moment, it’s all good because the friendship would have easily won out.

This opens the door to answering your question by letting him know your friendship is not changed by distance. It also gives him comfort to confide in you if he happens to be thinking the same thoughts as yourself without possibly making a regretted, awkward move on him. Instead of you risking it, you just set the complete picture with all the answers and gave him permission for the same without that risk to him, and with a promise that it’ll all be okay no matter what. It’s his move now.

At this point, he may ask direct questions. Be respectfully honest with him. You may offer that your bromance comment is born from picking up on alcohol induced mixed signals (seemingly a way a straight guy can claim innocence if called out), with acceptance of him (if it was his way of casually testing your boundaries) and apologizing if you misinterpreted, reminding him that you didn’t react out of respect for him and your friendship. If he directs the conversation more towards your desire, then great. Of course, you have to be prepared to accept that the answer may be that nothing is or will have changed. If that’s the case, it’s still great for you. Knowing that you have built and enjoy this special friendship and didn’t ruin it by challenging his trust, you have protected a great friendship that he has entrusted in you as well that you both can continue to comfortably enjoy and evolve naturally as it should throughout time.

Hopefully my thoughts are accurately communicated. It’s not my opinion to trick anyone into a situation, but to lay things out so both parties can actively participate in the best possible outcome. If I fall short in this post, I hope someone will get my intent and chime in to help out.
Everything you communicated in your post definitely made sense. We talked the other night about how our friendship is going to shift because we won't be hanging out all the time anymore, and we both expressed how grateful we are for having met each other and getting as close as we have. (It was actually kind of emotional). As of right now he's been the closest guy friend I've had in my whole life just because of how well we click. I feel like when we hang out together the thought of our sexualities goes right out the window, and we're just ourselves without labels. The thought of, "Oh shit, I'm straight...I shouldn't be acting this way", doesn't occur to him. (Which is amazing. Especially because of how societies standards can be).
In reality, I wish our friendship could just continue the way it is now and watch it play out, but now that there's a deadline, I want to take this opportunity to express myself and all my thoughts while I can. (Which is why this post was created in the first place).
All the positive feedback I've received so far in regards to this situation has been really helpful so far, and I really appreciate the time you guys have all taken to express your input. I think as of now I'm just going to express my thoughts to him and be honest, and whatever happens, happens. I don't want to live a life of regret and be stuck full of "what ifs" in the future. I mean, the goal of friendship is to be honest with each other right? Whatever the results end up to be and how he reacts, is just his truth, and I'm going to respect that whether it goes north or south. I just know kind of like what I've been pointing out, if don't, I'm going to regret it. And as my best friend, I feel like he deserves to know what my thoughts are, right?
 

Joguy07

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Everything you communicated in your post definitely made sense. We talked the other night about how our friendship is going to shift because we won't be hanging out all the time anymore, and we both expressed how grateful we are for having met each other and getting as close as we have. (It was actually kind of emotional). As of right now he's been the closest guy friend I've had in my whole life just because of how well we click. I feel like when we hang out together the thought of our sexualities goes right out the window, and we're just ourselves without labels. The thought of, "Oh shit, I'm straight...I shouldn't be acting this way", doesn't occur to him. (Which is amazing. Especially because of how societies standards can be).
In reality, I wish our friendship could just continue the way it is now and watch it play out, but now that there's a deadline, I want to take this opportunity to express myself and all my thoughts while I can. (Which is why this post was created in the first place).
All the positive feedback I've received so far in regards to this situation has been really helpful so far, and I really appreciate the time you guys have all taken to express your input. I think as of now I'm just going to express my thoughts to him and be honest, and whatever happens, happens. I don't want to live a life of regret and be stuck full of "what ifs" in the future. I mean, the goal of friendship is to be honest with each other right? Whatever the results end up to be and how he reacts, is just his truth, and I'm going to respect that whether it goes north or south. I just know kind of like what I've been pointing out, if don't, I'm going to regret it. And as my best friend, I feel like he deserves to know what my thoughts are, right?
Please don’t interpret this as judgmental, but if you’re going to remain friends, this is dangerous territory that should not be placed on a deadline when you will have other chances to hang out even after your move. You may regret not having an intimate physical memory made with him now, but regretting a lost friendship if he gets spooked is far harder to live with, especially down the road when you realize the true impact.

You do make a great point that he deserves to know your thoughts. As a third party, anyone can see and admire that. However, because you consistently present him as genuine and most recently mentioned the thought of “Oh shit, I’m straight…I shouldn’t be acting this way.” doesn’t occur to him, he may be blindsided with your confession and feel betrayed that you have other intentions with him when he has believed all along that he was in his safe place with you.

Only he knows if he’s teasing you or not.

A question in the back of my head is this:
When he was doing all these things, it was the perfect opportunity to be honest with him by saying something like “That’s really cute what you just did, and it’s cool, but you gotta know that as a gay guy who also has a few drinks in me, I’m worried that sometimes when you do that I can’t help it if it’s teasing me and my thoughts might carry me somewhere you may not like.”

One of two things can happen here. He sobers up in an instant and tucks himself back in, (insert reassurance and acceptance here), or a big grin takes over his face that he can’t get rid of. Green light, perhaps? If you mutually determine so, insert reassurance now and also after the fact because he needs to know without question that he can always trust you with his vulnerability to your new shared secret.

Again, his choice knowing it’s all good with you no matter what gives him the honor of participating verses being prey. He’s adorable. Out of respect for him, I believe the intent is that his experience should be equally as good as yours or it’s not worth doing. That alone should eliminate any chance of regret.

As another poster said, “things will go fine… if not then it’s not to be.” Open the door to the possibility and make a wish.
 

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First off. thanks for the compliment’s and hyping me up. Yes, my name is Jarren, and yes, that is me in my profile picture, lol. I think that pictures crap though but I'm glad to hear at least someone likes it. I want to clarify though, the love I have for "Adam" is just normal love. Like the kind of love that you have for someone close to you and really care about.
I don't feel at all as if our last night together would be a "hit it and quit it" type of situation, it's more like the "last hurrah" you were referring to. Sort of like the season finale of your favorite show. You're definitely right though about how we met. I obviously saw he was really attractive but I didn't seek out to be friends with him because I wanted to pursue anything sexual, it sort of just happened over time. If we do end up hooking up, I don't have any sort of expectations or desire for our friendship to go any further than that. I'm kind of just "shooting my shot" on our last night. I'm definitely starting to feel a lot more confident about doing it though because of some of the great feedback I've heard so far. In my mental "pro's and con's" list, the pro's are beginning to out outweigh the con's and I'm starting to have a much better perceptive on this whole situation thanks to all of you guys.
Obviously if this whole thing does go south, and I get rejected, then it is going to sting a little on my self esteem scale, but if I chicken out and decide not to say anything, that'll affect my "scale" as well just because of not having the confidence to speak up. It'll probably "haunt me" for the rest of my life in a way. I hope that all just made sense?
LMAO if you're that interested (which I have been too), you could frame it as a sort of "if you ever pondered being with a guy, I'm here for you" type deal. Like bring if up in the heat of a moment as a trusting and caring friend who wants to help a friend explore his own inner sexual desires that possibly have never openly crossed his mind. Not totally risk free but you could spin it in a humorous manner if you need to bail.
Or alternatively upon reading ur post earlier you could "cast a line"; throw out little jokes, comments, tidbits that may seem like harmless comments that can turn the tide and steer him in the direction where eventually he will do X, or clarify Y. Obvs it should be light and innocent starting off and be used sparsely or with care utilizing how you know your relationship dynamics work.

I've had a couple very intimate friends I was kinda unsure of (cuddle, sleep together, share food and drink, ect) that I cast out little comments and asked when we were both inebriated and got responses both times clarifying that they were in fact straight and 'I was the one guy they did that with' - one of them I let my lust get the better of me and I got rejected hard but we were so close it didn't affect the friendship aspect, although the cuddling definitely stopped which was all on me.

One final thing is there is a totally unfair aspect many straight guys I've known adopt; The "I can make gay jokes and 'passes' at you, but if you act interested, even in an overtly jokingly manor then that's not cool." Which I don't think is on purpose, but can be frustrating at times jokingly or sexually. This basically got me out of a straight friend group who they made homosexuals look like John Wayne. I talk to a couple ppl from the group still and apparently they all knew I was just joking, I'm a funny guy who likes to joke around - but the common response was "Yeah but YOU ARE bi" and supposedly that made most of them uncomfortable. Was only close to two people from there, it sucked but no biggie but that's how some people rationalize it.

Hope that last part doesn't discourage you but it is a different dynamic that can be hard to read. Hope you can get a definite answer before New Years and plan accordingly! plz keep us updated!
 

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Been there done that.
It can end up OK or end quite badly. You roll the dice.
The MAIN thing is you must NEVER initiate the sexual encounter. It must always be him, drunk or not.
He needs to see himself as the one in control and with the power to choose or reject.
It's also a waste of time in the end.
It never leads anywhere.
You have this fantasy he will discover you are his one and true love and you will live happily ever after. You wont admit it but it's there.
And it's an illusion. Move on.
 

Raybo Revoy

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Been there done that.
It can end up OK or end quite badly. You roll the dice.
The MAIN thing is you must NEVER initiate the sexual encounter. It must always be him, drunk or not.
He needs to see himself as the one in control and with the power to choose or reject.
It's also a waste of time in the end.
It never leads anywhere.
You have this fantasy he will discover you are his one and true love and you will live happily ever after. You wont admit it but it's there.
And it's an illusion. Move on.
And I would say you are spot on! Best comment I've seen - including mine!:laughing:
 

Chrismiller

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Damn I have so many divided opinions on this
One is: go for it!! Try to be sure he's comfortable with that and he'll be fine with it
Yeah u can be rejected but I guess that's better than wasting your time regretting for someone you were about to do :)
 
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Tuonela

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Been there done that.
It can end up OK or end quite badly. You roll the dice.
The MAIN thing is you must NEVER initiate the sexual encounter. It must always be him, drunk or not.
He needs to see himself as the one in control and with the power to choose or reject.
It's also a waste of time in the end.
It never leads anywhere.
You have this fantasy he will discover you are his one and true love and you will live happily ever after. You wont admit it but it's there.
And it's an illusion. Move on.
At best he is exploring and you could be part of this, or maybe not. Go with where he wants if that's what you want, or move on. It's rare but it does happen that a straight guy will be keen for fun on a regular basis NSA, humour him that he is straight, but you need to be OK with that in your mind and not expect more of a relationship than there is...