WIBTA if I enabled a friend's possible developing alcoholism?
I (28M) work with a guy we'll call Damien (27M). Hes a cool dude generally, we're kinda friends but since I've known him a couple years now I know if one of us were to quit we likely wouldn't see each other again bc he's not especially social. for the purposes of full disclosure I'll also say I've had a crush on him for the majority of the time I've known him, he knows this and I've accepted that it's unlikely to go anywhere because he's probably the least emotionally available person I've ever met, but I'd still like to do physical stuff with him sometime if he'd be open to it.
Damien seems to kinda...hate himself a bit. it's clear he struggles with some mental health issues and I've told him he can talk to me about stuff but I haven't pried too deep on the specifics, because I'm not his therapist and if he wanted to tell me he would. he's expressed suicidal ideations in a half-joking way before and has pretty much ignored when I've expressed concern/distress over them. and he's been chatting lately about how he has been getting drunk like, every night. I've mentioned offhandedly how that's probably not great for him and he agreed, but is still doing it.
anyway he also knows how to repair Nintendo switch systems and enjoys doing so. a couple years ago (when we hadn't known each other very long and I'd JUST developed feelings for him) he fixed my analog stick when it started drifting. I repaid him with dinner. now my stick is drifting again and my case is cracked, so I've brought up the idea of him fixing the stick and changing the case out with dinner and booze (I enjoy drinking too, just like...only every other weekend or so). he seemed enthusiastic about the idea.
I expressed to him that it would be a RESPONSIBLE amount of booze and that if he drank at my house I'd be hiding his keys till he sobered up so he couldn't drive drunk. I also don't have any intentions to do anything inappropriate with him (even in the unlikely event that he initiated anything, I'd insist on talking about it sober first) besides the same level of joke-flirting i already do at work. I just want him to have a fun time and to fairly repay him for his work (I don't make very much money, and he hasn't asked for monetary payment), but I'm worried that I shouldn't be participating in what seems to be developing into a bad habit for him.
TLDR friend seems to be drinking a little too often, but I offered him dinner and booze as payment for some light repair work.
Shouldn't have included alcohol in the deal, but also if he's that badly off, like... Look. I feel like a lot of folks in the replies, and also you, OP, don't really..."get" what starts addictions. If he is turning to alcohol in order to make life bearable, as I am inferring from your ask, then the alternative is...probably attempted suicide.
If alcohol is keeping him alive, then that's not a bad thing. As his friend, and especially as someone who has a crush on him, you...probably should be presenting him with positive experiences that don't revolve around alcohol. With addiction/developing addiction, it's so, so important to help develop a connection between joy and sobriety.
It's not your job to do this, not at all: but the way to step away from addiction is to have a happy enough life that one does not need the substance to find life bearable. If you want to be a source of sober joy for him, then you need to provide that. If not, then what's the point of even having a crush?
But. again. addiction helps keep people alive when sober life is unbearable. So many people in the replies are urging you not to encourage it, and they're right, in a way, but this is a bigger issue than you can handle. This is a bigger issue than he can handle, and obviously so, as he seems to be turning to alcohol specifically because he cannot handle it.
You messed up in this specific instance, but your insistence that it only be a specific amount of alcohol was a smart move. (Re)learning moderation is really difficult. In the future, I would advise you not mix alcohol with your time together. Still, I would also not back out of the alcohol in this case, because you had already offered it, and to an addict, that'd be really shitty and also something that could drive him further away from others.
He needs help that you can't provide. You made a mistake. You can still do better in the future. The fact that you're at all concerned is a good sign. I hope things turn out all right.