TIFU by giving straight friend the wrong idea…

TLDR: Took a childhood best friend on a fancy vacation over New Years, he thought he needed to repay sexually.

So this actually happened over NYE but it took until recently to work things out enough that I can share the story.

So as context, this is not meant to brag, but I grew up very modestly lower-middle-class in a small suburban neighborhood. After college, a really good tech job plus right-place-right-time led me to be really well off. However, socially it’s been a mess — I don’t feel like I really bond with the people I work with or the high income social scene. I really like my childhood friends, so sometimes I will take them along to a nice fancy vacation.

I have an estranged relationship with my parents so the holiday season is time I spend vacationing with friends and chosen family. This year, a (straight male, 30s) childhood friend and I were connecting about being tired of cold winter and I convinced him I needed a vacation buddy to try out a resort in Maui. I offered to pay for everything (flights, 2-separate-bedroom hotel suite, meals especially if I select an expensive restaurant) and he accepted. Like it was maybe $20k ish. Expensive but not outrageous like chartering a yacht or anything.

We were having an absolute blast on the vacation, but one night over cocktails our conversation drifted into the area of “casual hookups” and I mentioned, as a bi male, my partner and I have been in an open relationship for 10 years and how for queer men casual hookups are often fun and low friction. It sometimes happens at dinner parties, vacations, etc. Again I was pretty drunk otherwise I self-filter this subject area amongst straight friends. Drunkenly I also was holding back tears, telling him how he was the first person I felt comfortable coming out to, and how I’ve always been grateful for how open minded he was in a fairly conservative/religious town.

Well on the last night of the vacation, after cocktails / happy hour, I excused myself early to shower (in my own en suite bathroom), because we had early flights. When I got out, I walked in to my friend, seemingly naked, in my bed half under the covers. I was like “umm hi, what’s up?” And he was practically shaking, nervously saying “I’m pretty sure this won’t be my cup of tea but thank you so much for this trip of a lifetime…”. Of course I immediately course-corrected HARD, repeating over and over again that there’s absolutely no strings attached, I’m going to walk back into the bathroom, and you’re gonna get dressed, and we won’t ever speak of this again.

The last day and the following week were extremely awkward and silent. Finally over the weekend we chatted again and cleared up the misunderstanding. He’s mostly embarrassed how he understood things and was afraid he came across “homophobic” or judgemental for assuming I wanted to have sex. I on the other hand was equally mortified that what I had intended as a “let’s do something fun with my disposable income” came across to him as some sort of sugar daddy arrangement, especially with that earlier conversation about hookups in mind.

Things are still a little awkward and I still haven’t found the right time or opportunity to fully explain myself, especially in terms of why I’m in this weird lonely-but-not situation and want to share experiences with friends while I’m still young and healthy enough to travel.