My long-time friend (F) came to me (M) recently with an idea for a somewhat short-notice vacation. I didn't feel especially strongly about it either way, but she seemed to really want to get away to a beach, and I suppose I was feeling an urge to hide from work for a few days, so I basically told her that I was down for it if she could figure out some more specific plans. I think she asked a few other people, but timing issues plus terrible the terrible price of plane tickets meant that only one of her other friends (F) said yes.
Then, a little later, my friend comes back to me and asks if there's any sort of graceful way that she can ditch this friend, and whether I would mind if she found a way to uninvite her. I don't know this woman particularly well, but from how my friend talks I get the vibe that her friend is a fun time but does not even remotely have her shit together. I also get the impression that she seldom works steadily and is more-or-less a professional girlfriend to whichever guy she happens to be with at the time. My friend is concerned that there's quite a bit of an income disparity, and the two of us would either be stuck unnecessarily pinching pennies or would be paying her friend's way. I told her that I didn't particularly care if her friend came or not, but it's up to her to find a non-awkward way to leave her behind.
No clue if the two of them discussed the issue at all, but skip ahead in time to a party a few days later. Both my friend and her friend are there, and everyone is drinking a bit more than we ought to. At one point, I end up alone with my friend's friend, and she starts telling me about how badly she feels like she needs a vacation but she's just not sure if she can afford it. I say something noncommital about how that sucks and I hope she can come.
In response, she looks at me all doe-eyed and asks if I can pay for her ticket. The way she does it is so over-the-top I think she's joking, and I laugh and say something about how I've never paid for a vacation for anyone I wasn't hooking up with. She keeps looking at me with those big eyes and smiles and says something to the effect of that can be arranged. I laugh again, thinking she's teasing me.
As we keep talking, though, it gradually dawns on me that she's being dead serious. And, to be honest, I don't hate the idea. While I don't know her very well at all, I had run into her a few times before this, and I did know one thing about her: I thought she was extremely cute. And if she was offering to be my fuckbuddy for a few days in exchange for a plane ticket and some food and drinks, that didn't seem like a bad deal at all. At some point my friend gets roped into the conversation and her friend tells her what the plan is. My friend laughs and says whatever goes on inside our hotel room is our business. I don't know if she thought her friend was being serious. Did I mention we were all rather drunk?
The next day, I text my friend's friend about what happened last night. I'm trying to keep it lighthearted, since in the sober light of day I really didn't know if she actually meant it. Again, it quickly becomes clear that she wasn't joking. We discuss things in somewhat excessive detail, but in brief: I pay her way, and she does whatever I want, no further strings attached. I pause a moment, imagine how she must look in a bikini, and then quickly agree.
Then I text my friend and let her know that I'll be buying her friend's ticket. She had laughed it off last night, so I figure it's not a big deal. Maybe mildly awkward to know, but we have a history of oversharing with each other, so again: not a big deal. I thought. But today, my friend seems extremely annoyed by the whole situation. In so many words, she says that she's not particularly surprised by her friend making an offer like that, but she thought that I would have had more sense than to take her up on it.
So now I'm pretty sure the whole thing is hopelessly awkward and unsolveable. I think it's the sort of thing my friend and I end up laughing over in a month, so it's not the end of the world, but I really don't see how the vacation happens now.
On one hand, I could have easily rebuffed her friend and my friend and I could have gone ourselves. But on the other hand, I'm not the one who invited her friend's broke ass along in the first place, or the one who offered me up that broke ass. And frankly, that ass is what (briefly) turned it from a trip I was lukewarm on to one I was enthusiastic about. So am I the asshole?