So I turn 60 next month

[RIPT2.0]

Hard to believe, I know, but it's true. I was drinking at my best friends house yesterday and said that I had thought of going on some grand adventure to celebrate the occasion but decided against it because I didn't have anyone to travel with. In my younger days I would have probably not thought twice about setting off on a solo trip but I'm just not as daring as I used to be, plus I don't play well with strangers. They tend to piss me off.

Anyway, my Buddies Wife said that she'd like to go on a trip with me and my Buddy ENCOURAGED it! True, they're more roommates than they are husband and wife. They sleep in different rooms and haven't had sex in at least 10 years. I don't think she's ever cheated on him but I know he has cheated on her. Numerous times. And she's aware of that. In fact, he's always telling me I should move in with her so he can move out because she can't afford to stay in the house alone.

Now, I like her a lot. She's been there for me many times when I needed help but I have never made a pass at her, or anything even close. Although my Buddy seems to be serious when he tells me I should hook up with her so he can go his own way I don't believe he'd ever forgive me if I actually did. How fucked up do you have to be to tell your best friend that he should hook up with your Wife anyway? The whole thing was just weird. Even though they no longer have a romantic relationship and argue all the time, I still believe they care a lot about each other. If they were divorced and living apart from each other, then I would look at this differently.

[oettinger]

Go for it. I like your place though (atleast what I got from skyping), giving that up would suck

[Rye and Coke]

Hard to believe, I know, but it's true. I was drinking at my best friends house yesterday and said that I had thought of going on some grand adventure to celebrate the occasion but decided against it because I didn't have anyone to travel with. In my younger days I would have probably not thought twice about setting off on a solo trip but I'm just not as daring as I used to be, plus I don't play well with strangers. They tend to piss me off.

Anyway, my Buddies Wife said that she'd like to go on a trip with me and my Buddy ENCOURAGED it! True, they're more roommates than they are husband and wife. They sleep in different rooms and haven't had sex in at least 10 years. I don't think she's ever cheated on him but I know he has cheated on her. Numerous times. And she's aware of that. In fact, he's always telling me I should move in with her so he can move out because she can't afford to stay in the house alone.

Now, I like her a lot. She's been there for me many times when I needed help but I have never made a pass at her, or anything even close. Although my Buddy seems to be serious when he tells me I should hook up with her so he can go his own way I don't believe he'd ever forgive me if I actually did. How fucked up do you have to be to tell your best friend that he should hook up with your Wife anyway? The whole thing was just weird. Even though they no longer have a romantic relationship and argue all the time, I still believe they care a lot about each other. If they were divorced and living apart from each other, then I would look at this differently.

You're right, the relationship is trash at this point, but let someone else put the nail in that coffin. Don't let it fall on your head. You're friends with both, keep it that way. Even though they're obviously ready to move on, i believe her first attempt to do so will be a shit show. Her second may be fine, but that first attempt is going to suck. This goes double true if YOU don't see her like that.

Be their friends, be there for both of them, but the risk to reward doesn't favor you when things inevitably go wrong.

Now, if you actually do have feelings for her, throw caution to the wind. But from what I read, you don't. So I'd let it go.

[Badfellow]

You're right, the relationship is trash at this point, but let someone else put the nail in that coffin. Don't let it fall on your head. You're friends with both, keep it that way. Even though they're obviously ready to move on, i believe her first attempt to do so will be a shit show. Her second may be fine, but that first attempt is going to suck. This goes double true if YOU don't see her like that.

Be their friends, be there for both of them, but the risk to reward doesn't favor you when things inevitably go wrong.

Now, if you actually do have feelings for her, throw caution to the wind. But from what I read, you don't. So I'd let it go.

Probably the best advice you're bound to get on the situation.

Oh, and Sammy, a happy 60 to you in advance. Clink and drink, fellow Drunkard.

[RIPT2.0]

Rye and Coke is a wise drunkard. I shall follow thine advice.

[Patchez]

Go on vacation, enjoy her company, let her buy you drinks but for fuck's sake keep your pecker in your pants.

[Artful Drunktective]

As long as the dude is 100% down for it where your friendship won't be compromised, why not go for it? For the most part it could be a win-win for all parties involved. I myself have been in a similar situation in the past and it worked out for everyone. But don't be giving up your hacienda right away or even move in together as that is pretty hasty. You don't want her to become your problem if shit doesn't work out and then she still can't afford it if one of you were to leave.

[RIPT2.0]

I'm not sure my friendship with my Buddy wouldn't be compromised, no matter what he says, if I hooked up with his wife. He's Italian and they're very possessive. And no way in hell would I move in with her and give up my digs. I'm in the process of putting a lot of money into this house because this is where I am going to live until the day I die. Period. She can't control her spending, which is a big issue during their many arguments, and I am not going to pick up her tab. Ever.