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

Jarren.Anthony

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Straight bros can be very affectionate with each other. Hugging and being playful, even naked or in a homoerotic way are pretty common among jock types. That doesn't mean he's gay or bi at all. It just means he sees you as as his bro, as one of the guys. Personally I wouldn't recommend trying to initiate anything more unless you're willing to possibly ruin your friendship. (I doubt he'd drop you altogether, but if you make him feel uncomfortable you might just grow apart)

Just think of it this way: if he is bi or interested in experimenting, and he's interested in doing that with you, he will try to initiate. If that happens you can just be completely receptive to it and see where it goes. The upside of this approach is that you'll feel great if it actually does happen - you won't have to worry about feeling you 'tricked' him or if you did something bad that damaged the relationship.
This is exactly what's been flowing through my mind this whole time. The first part was spot on. In regards to the second, the only part that I question is his actual confidence to initiate. Sort of like that, "we're both waiting for the other person to say I love you" kind of thing. (but not in that pretext) Since it'll be the last time I see him for a while, or maybe even ever, the fear I have about "messing things up for the future" is definitely decreased. I think what I've come to so far is that if things go as they usually go, I'm just going to speak up and say something. Initiating something physical without knowing if he's on the same page or not feels wrong in a sense. I know people do it, and I know it does have success, but for me I think saying something would be the better route. Something maybe like "hey, I know we play around a lot and have fun messing around, but since it's my last night here and we won't be seeing each other for a while, if you're interested in trying something a bit more, I'd be open to that". Or maybe something around those lines?

Geez I feel like such a little girl. If you guy's knew me in person and heard me say this, you'd all be like what the fuck Jarren.
 

C4junG0n3_BAD

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I'm going to say the thing everybody is avoiding. I've snaked on straight guys before. I'm not proud of it, but I have. I've gotten guys drunk. I've tricked guys. Things went my way sometimes and sometimes they didn't. None of said experiences were without problems. I had a thing with a straight guy for years. Yea Yea Yea I know everybody is gonna say he ain't that straight. Who cares? Anyway that particular one was weird as hell. I don't recommend it to anyone. Most every time I did this, it was because I was selfish and thought I was entitled to what I wanted...his body.

If you are sexually attracted to guys and like to have sex with them, then the best thing is to pursue like-minded guys. The outcomes will be much better. Most of my buddies all my life have been straight guys. I never really fit into the "gay lifestyle" whatever that is. The good thing about straight guys, no matter how hot they are, is you know they are off the menu....period. The spare few times I forgot that all important rule, I was invariably disappointed.

Every one of those times was not some guy kissing all over me or cuddling with me. Now I've bathed with guys, slept in the same bed, eaten off the same plate, hell eaten off the same fork, used my bud's toothbrush. I've manscaped some guys for IFBB comps. I've shaved balls for crying out loud. I even checked out a bud's perineum because he thought there was something way bad going on down there. When there is deep trust, secure straight guys have no issue with same gender physical contact, even if it is very intimate. If you think that is not true you have bought into a nonsensical feminist myth.
 

CockMySuck

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So much discouraging advice.

My advice: Just do it. It's better not to repress your feelings and desires. It's not good to have the elephant in the room of you being into him and not saying something. If he's a good enough friend, offering to hook up with him won't hurt the relationship and will only lead to a "sorry, not interested" and you keep going. I would encourage you to not overthink it, and just be open with your friend about how you're feeling and ask. As long as you're not pushy, creepy, and respect their response, everything will be fine. When I've seen this not work out, it's been when the "straight" guy is homophobic or deeply traditional. If your friend isn't homophobic or deeply traditional, you telling them you're open to sex shouldn't be a huge deal. In fact, if he's a good enough friend, as I've experienced, he won't even be surprised that you're telling him this and has possibly already picked up on it.
 

Brettdude3

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I don’t understand why you’re waiting until NYears eve to figure this out. If you’re totally open and talk to him while he’s all over you and he agrees to do something more, think of all you can experience with eachother over the next month before you leave. You have nothing to be ashamed of if you do it all on the level and don’t “trick” him the night before you leave. If he doesn’t go for anything else, you still have a month to build the bro relationship as you are so it doesn’t get weird. Also…I agree. Guys get hard…feel free to show some wood around him.
 

C4junG0n3_BAD

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So much discouraging advice.

My advice: Just do it. It's better not to repress your feelings and desires. It's not good to have the elephant in the room of you being into him and not saying something. If he's a good enough friend, offering to hook up with him won't hurt the relationship and will only lead to a "sorry, not interested" and you keep going. I would encourage you to not overthink it, and just be open with your friend about how you're feeling and ask. As long as you're not pushy, creepy, and respect their response, everything will be fine. When I've seen this not work out, it's been when the "straight" guy is homophobic or deeply traditional. If your friend isn't homophobic or deeply traditional, you telling them you're open to sex shouldn't be a huge deal. In fact, if he's a good enough friend, as I've experienced, he won't even be surprised that you're telling him this and has possibly already picked up on it.
Says the guy that thinks all straight guys will go for the right gay man eventually. I've never seen that happen in my life ever. "It's better not to repress feelings and desires" , what planet do you live on? Being a "good enough friend" really...so he owes something to the guy that is lying, because of friendship. I don't know people that think that way. Nobody owes anyone anything. If he thought the guy was making a move he should have said something...THEN. The reason he didn't say something then was he knew it wasn't a come-on. I've been down this road. When I forced my "desires" on the other guy. Once I got a broken nose. The other I had my life completely destroyed by a vindictive girlfriend and her incredibly wealthy connected father. So yea do that. It was tons of fun.
 
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Jarren.Anthony

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The only reason I have some doubt about doing it sooner is because of the thoughts some people have said so far about it "possibly ruining the friendship". It's kind of scared me off to be honest. I do think some others were right about the, "since our friendship is as close as it is, it shouldn't change anything", but I think it's more going to affect me because of the paranoia thinking it affected him, even if he says it didn't. It'll be so much easier to process whatever the results are afterwards though just because I won't be seeing him again for quite a while. On a comparison scale, keeping our relationship the way it is is at a 65%, and progressing something more is at a 35%, if that makes sense? The only reason it keeps coming up in my mind is because of the feeling of pure regret I'm going to have afterwards by cowering out and never knowing. I've just decided to wait until the last time we're going to see each other though because of the worry some of you have expressed, and also just because it personally gives me a reason to keep putting it off, lol.

Personal message to C4junG0n3_BAD though, I really appreciated the input in your first message, but I don't particularly agree with how you're tearing down others input as well. I really am genuinely grateful to hear everyones thoughts but I also don't want anyone to feel like their perceptive on the situation is going to be belittled afterwards.

Thanks guys!
 

CockMySuck

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Says the guy that thinks all straight guys will go for the right gay man eventually. I've never seen that happen in my life ever. "It's better not to repress feelings and desires" , what planet do you live on? Being a "good enough friend" really...so he owes something to the guy that is lying, because of friendship. I don't know people that think that way. Nobody owes anyone anything. If he thought the guy was making a move he should have said something...THEN. The reason he didn't say something then was he knew it wasn't a come-on. I've been down this road. When I forced my "desires" on the other guy. Once I got a broken nose. The other I had my life completely destroyed by a vindictive girlfriend and her incredibly wealthy connected father. So yea do that. It was tons of fun.
Step away from the computer and touch grass, my friend. Stop projecting your shit, boomer experiences onto other people. Alas, reading comprehension is fundamental, because none of that responded to anything I said or was thinking. Live and let live, please, this doesn't need to be a debate.
 

CockMySuck

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The only reason I have some doubt about doing it sooner is because of the thoughts some people have said so far about it "possibly ruining the friendship". It's kind of scared me off to be honest. I do think some others were right about the, "since our friendship is as close as it is, it shouldn't change anything", but I think it's more going to affect me because of the paranoia thinking it affected him, even if he says it didn't. It'll be so much easier to process whatever the results are afterwards though just because I won't be seeing him again for quite a while. On a comparison scale, keeping our relationship the way it is is at a 65%, and progressing something more is at a 35%, if that makes sense? The only reason it keeps coming up in my mind is because of the feeling of pure regret I'm going to have afterwards by cowering out and never knowing. I've just decided to wait until the last time we're going to see each other though because of the worry some of you have expressed, and also just because it personally gives me a reason to keep putting it off, lol.

Personal message to C4junG0n3_BAD though, I really appreciated the input in your first message, but I don't particularly agree with how you're tearing down others input as well. I really am genuinely grateful to hear everyones thoughts but I also don't want anyone to feel like their perceptive on the situation is going to be belittled afterwards.

Thanks guys!
I get that and love that for you. I know from personal present experience that the regret or feelings will remain if you don't do something to address them or address the elephant in the room. There's definitely a delicate way to do that and sometimes you need to trust your own intuition about how to communicate with your friend without losing him. I believe in you, because you are so thoughtful about the situation. If you did lose this friend for some reason, maybe that friendship wasn't meant to be; there will be other close friends, including those who will be okay with, appreciate, and sometimes even reciprocate those feelings for you. That's the thing that I've been surprised to learn, that I haven't lost friends by opening up about being understandably into them. I feel like my/our generation – younger generations – can actually do that without it being weird like it was for older generations.
 

C4junG0n3_BAD

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Step away from the computer and touch grass, my friend. Stop projecting your shit, boomer experiences onto other people. Alas, reading comprehension is fundamental, because none of that responded to anything I said or was thinking. Live and let live, please, this doesn't need to be a debate.
Well, I've lived long enough for it to happen. Not that it hasn't happened before. I suppose the more things change, the more they stay the same. I was just as hostile toward old queers when I was young. Funny, you never think you'll ever be THAT old. I certainly didn't with my lifestyle.

It isn't a debate. I was honestly trying to offer sound advice. I've known a lot of guys that actually thought everyone was on the table. I think that might come from commercially produced gay porn. The "straight man" scenario seems to be in all that type media. It has become more indistinct in later years which actually exaggerates the idea that 100% of men are possible partners. That coupled with many current social factors does lead gullible people astray. It doesn't work that way. It never has. It never will. Sex is sex. It isn't love. Friendship based on sex isn't friendship. A true friend is worth more than a million one-night-stands.

If Jarren thinks he is actually in love with this guy, I can't advise on that. I've been there. You can't really control love. What ever that is! It is as mercurial as the tide. I've been in pretty much the same situation. I'm here to tell you. Straight guys do stuff that gay guys take as a come on. It isn't, no matter how much you want it to be.

My concern is once the words are out there, you can't take them back. That is what happened to me. I lost not only the guy I told about my feelings, but 5 other friends as well. I know people are going to do the, "they weren't really friends if they were like that." Maybe not, but it still hurts like hell. I've said many things I wish I hadn't in my life. Many were in these very type situations. The thing is these type things have an eerie tendency to spread without it being known.

I don't know this kid. I don't know Jarren. (Cool name by the way) I only know what has been related here. Jarren refers to this guy as his "best" friend. So, I'm thinking Jarren is not the type of guy that worms his way into a friendship with a guy because he is handsome and he wants a shot at "doing" him. I could be wrong about that. It happens. There are guys that do that on both sides. I've had straight buddies do that to girls. I'm not proud of it, but I've done it. The difference is, I would never refer to that person as a "best" friend. Now the part about doing it on a specific night so he won't have to see him again is a bit unsettling. That sounds like a "hit it and quit it" deal. That doesn't match up with Jarren's agonizing over this.

Jarren relates that this type behavior only occurs when inebriated. Maybe the buddy is using it as an excuse to do stuff with Jarren. That doesn't sound right but I'm sure it is plausible. If that is Jarren in the icon, then he is a way handsome guy which probably doesn't have a problem with getting a guy. The point I'll make here is if this guy was interested, drunk or not, he wouldn't have difficulty in getting a boner.

No. It seems to me that Jarren honestly has actual feelings for this guy. He might even feel like he is falling in love with him....or at least headed that way. This sounds like a guy that knows exactly what is going on and wants a last hurrah before everything invariably goes south after the big reveal. I've been in that exact predicament. What you think is going to happen and what actually does happen will not the identical.
 

Jarren.Anthony

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I get that and love that for you. I know from personal present experience that the regret or feelings will remain if you don't do something to address them or address the elephant in the room. There's definitely a delicate way to do that and sometimes you need to trust your own intuition about how to communicate with your friend without losing him. I believe in you, because you are so thoughtful about the situation. If you did lose this friend for some reason, maybe that friendship wasn't meant to be; there will be other close friends, including those who will be okay with, appreciate, and sometimes even reciprocate those feelings for you. That's the thing that I've been surprised to learn, that I haven't lost friends by opening up about being understandably into them. I feel like my/our generation – younger generations – can actually do that without it being weird like it was for older generations.
Thank you so much for saying this dude! Everything you said made a lot of sense and it's awesome you can relate to that feeling of regret too if you don't go through with something you're interested in. I definitely feel you on how our generation today is much different than it used to be. I feel like we're much more openminded when it comes to situations like this and have more acceptance for it. I'm definitely not bashing or talking for older generations because I've obviously only lived in mine, but I just know if I express interest, I won't be thrown in jail and get rocks thrown at me. I completely feel you on going into this delicately and trusting my intuition. If during our last night he doesn't flirt or do any of the things he normally does, then I'm never going to bring it up. I'm just going to go with the flow. I don't want us to be playing Call of Duty and randomly just pause it to say my speech, lol.
 

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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)
Go for it. In 10 years - what would u rather regret? Not doing it, trying and going for it? Or risking him getting upset?
 

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I mean it's easy to think that it "shouldn't affect your friendship" is easy when you consider it from your perspective. You're you, you're your own ally and view your own actions with a completeness that the cannot, since he's not you.

Imagine reversing the situation: say you have a girl who's a great friend (assuming for a moment you're completely gay, as he might be completely straight). You spend a lot of time together, you're comfortable together, you tell her your secrets, she tells you hers. Then one day when you're chilling together and you're drunk, she suddenly starts trying to seduce you, touching your dick, trying to kiss you. You would tell her you're not interested. But how would you feel afterwards? As a gay guy being seduced by a woman is unwelcome, especially a woman you consider your friend. Do you really feel like you'd see her in the same light? Would you still be as open with her after that? Because I sure wouldn't. If I found out one of my girlfriends was in love with me, I probably wouldn't drop her as a friend, but I absolutely would treat her differently and keep her at arm's lenght.

Just to put it this way: from your perspective, the idea of trying to hook up with him and maybe being successful is exciting, and hot. But from his perspective, if he's straight, it's not hot and exciting at all - it's just unwelcome. The same way that for you if a girl you're friends with tried to seduce you it wouldn't be hot for you at all, it would just be awkward and weird and you would just want it to stop.
 

Jarren.Anthony

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Well, I've lived long enough for it to happen. Not that it hasn't happened before. I suppose the more things change, the more they stay the same. I was just as hostile toward old queers when I was young. Funny, you never think you'll ever be THAT old. I certainly didn't with my lifestyle.

It isn't a debate. I was honestly trying to offer sound advice. I've known a lot of guys that actually thought everyone was on the table. I think that might come from commercially produced gay porn. The "straight man" scenario seems to be in all that type media. It has become more indistinct in later years which actually exaggerates the idea that 100% of men are possible partners. That coupled with many current social factors does lead gullible people astray. It doesn't work that way. It never has. It never will. Sex is sex. It isn't love. Friendship based on sex isn't friendship. A true friend is worth more than a million one-night-stands.

If Jarren thinks he is actually in love with this guy, I can't advise on that. I've been there. You can't really control love. What ever that is! It is as mercurial as the tide. I've been in pretty much the same situation. I'm here to tell you. Straight guys do stuff that gay guys take as a come on. It isn't, no matter how much you want it to be.

My concern is once the words are out there, you can't take them back. That is what happened to me. I lost not only the guy I told about my feelings, but 5 other friends as well. I know people are going to do the, "they weren't really friends if they were like that." Maybe not, but it still hurts like hell. I've said many things I wish I hadn't in my life. Many were in these very type situations. The thing is these type things have an eerie tendency to spread without it being known.

I don't know this kid. I don't know Jarren. (Cool name by the way) I only know what has been related here. Jarren refers to this guy as his "best" friend. So, I'm thinking Jarren is not the type of guy that worms his way into a friendship with a guy because he is handsome and he wants a shot at "doing" him. I could be wrong about that. It happens. There are guys that do that on both sides. I've had straight buddies do that to girls. I'm not proud of it, but I've done it. The difference is, I would never refer to that person as a "best" friend. Now the part about doing it on a specific night so he won't have to see him again is a bit unsettling. That sounds like a "hit it and quit it" deal. That doesn't match up with Jarren's agonizing over this.

Jarren relates that this type behavior only occurs when inebriated. Maybe the buddy is using it as an excuse to do stuff with Jarren. That doesn't sound right but I'm sure it is plausible. If that is Jarren in the icon, then he is a way handsome guy which probably doesn't have a problem with getting a guy. The point I'll make here is if this guy was interested, drunk or not, he wouldn't have difficulty in getting a boner.

No. It seems to me that Jarren honestly has actual feelings for this guy. He might even feel like he is falling in love with him....or at least headed that way. This sounds like a guy that knows exactly what is going on and wants a last hurrah before everything invariably goes south after the big reveal. I've been in that exact predicament. What you think is going to happen and what actually does happen will not the identical.
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?
 

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I'm definitely not bashing or talking for older generations because I've obviously only lived in mine, but I just know if I express interest, I won't be thrown in jail and get rocks thrown at me.
Hi: Two and 1/2 cents from the "older generation", lol.

A wise person once gave me what has proven to be very sage advice about situations in which one may not know the outcome.

And that was to think it through before you act. Make sure that you can live with the consequences.

Ask yourself the questions:

1. What's the best that could happen if I hit on him?
2. What's the worst that could happen if I hit on him?

Best case scenario is you now have a friend with benefits.
Worst case scenario could be you no longer have a friend.

Good Luck and Best Wishes to you! :)
 

Jarren.Anthony

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I mean it's easy to think that it "shouldn't affect your friendship" is easy when you consider it from your perspective. You're you, you're your own ally and view your own actions with a completeness that the cannot, since he's not you.

Imagine reversing the situation: say you have a girl who's a great friend (assuming for a moment you're completely gay, as he might be completely straight). You spend a lot of time together, you're comfortable together, you tell her your secrets, she tells you hers. Then one day when you're chilling together and you're drunk, she suddenly starts trying to seduce you, touching your dick, trying to kiss you. You would tell her you're not interested. But how would you feel afterwards? As a gay guy being seduced by a woman is unwelcome, especially a woman you consider your friend. Do you really feel like you'd see her in the same light? Would you still be as open with her after that? Because I sure wouldn't. If I found out one of my girlfriends was in love with me, I probably wouldn't drop her as a friend, but I absolutely would treat her differently and keep her at arm's lenght.

Just to put it this way: from your perspective, the idea of trying to hook up with him and maybe being successful is exciting, and hot. But from his perspective, if he's straight, it's not hot and exciting at all - it's just unwelcome. The same way that for you if a girl you're friends with tried to seduce you it wouldn't be hot for you at all, it would just be awkward and weird and you would just want it to stop.
This is exactly where my mind is at when it comes to my "con's" list! I really liked your analogy. The biggest mystery of it all though, referring back to your analogy, is the "gay guy" not being fully gay or not, or maybe just so trusting in this girl that he'd really be open to the fact of taking it further, but since it's all new to him he just doesn't know how to. The analogy doesn't include the fact that the "gay guy" is leading her on a lot too for her to think and act that way.
I also just want to point out too that when "Adam" does say what he says and acts the way he does, I'll return the same energy, but I've never been the first one to initiate that sort of behavior just because I respect his comfortability, and also just because it would be really weird for me to just sit there and flirt with him all night on my own without a reason. It sounds desperate in a way. I only return what he gives me.
 

C4junG0n3_BAD

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I mean it's easy to think that it "shouldn't affect your friendship" is easy when you consider it from your perspective. You're you, you're your own ally and view your own actions with a completeness that the cannot, since he's not you.

Imagine reversing the situation: say you have a girl who's a great friend (assuming for a moment you're completely gay, as he might be completely straight). You spend a lot of time together, you're comfortable together, you tell her your secrets, she tells you hers. Then one day when you're chilling together and you're drunk, she suddenly starts trying to seduce you, touching your dick, trying to kiss you. You would tell her you're not interested. But how would you feel afterwards? As a gay guy being seduced by a woman is unwelcome, especially a woman you consider your friend. Do you really feel like you'd see her in the same light? Would you still be as open with her after that? Because I sure wouldn't. If I found out one of my girlfriends was in love with me, I probably wouldn't drop her as a friend, but I absolutely would treat her differently and keep her at arm's lenght.

Just to put it this way: from your perspective, the idea of trying to hook up with him and maybe being successful is exciting, and hot. But from his perspective, if he's straight, it's not hot and exciting at all - it's just unwelcome. The same way that for you if a girl you're friends with tried to seduce you it wouldn't be hot for you at all, it would just be awkward and weird and you would just want it to stop.
I really don't like females at all. Unfortunately, like every female I know, they don't think any of that is true. The woman's perspective is that they are all goddesses. LOL That's the thing I like about guys...well guys into guys. You try. It's either a yes or a no. You go on from there. If you've gone off the reservation. (I've done it a few times.) You might get punched out. You might end up in the hospital. It is what it is. Women just won't go away. I've had this happen twice. Not even close to either of them. Nothing that could possibly be misinterpreted. It was beyond annoying.

I've done stupid crap like thinking a guy was coming on to me when he clearly wasn't. I went full steam ahead because I wanted what I wanted and didn't care what the fallout would be. Well, I didn't think I'd care what the fallout would be. Turns out I did care... a lot. I ended up in the hospital once. I did the ER once. Lost tons of friends every time this occurred. One of these excursions cost me my job, house, car and the few shreds of reputation I had left. So yea there's that.
 

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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?