Skip to main content

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.

Labels:

Comments

Post a Comment

Popular posts from this blog

TIFU - Don’t do what I did

On Sunday morning Aug. 24th, I awoke to discover a large blind spot in my right eye, which turned out to be what is called wet age-related macular degeneration (AMD). It has resulted in a very significant, permanent loss of vision in that eye. Although I maintain good peripheral vision, whatever I focus on at best is very blurry, and mostly disappears. I can barely make out the large E at the top of the eye chart. If this happens to my left eye I’ll be unable to read or drive. It turns out that I missed the opportunity that I had to prevent this from becoming a serious problem because I failed to report what appeared to be minor changes in my vision. In the weeks prior to August I had noticed that what I knew to be straight lines appeared to my right eye to have a little waviness. I also noticed that the color of my front lawn, which I could see through the window from my recliner,  was subdued, looked almost gray, in my right eye. So I scheduled an eye exam, which revealed the p...
Post a Comment
Read more

TIFU by getting suspended for 2 days by my front office in school.

I (13M) am an African American student at Jeannette junior high who had got suspended for 2 days here. I was in math class minding my business until my teacher had told me to go to the main office, which posed no problem to me. As i went down there, the people of the front office had stopped me and made me get a new ID (yes, we have id's.) so i had asked them if i could maybe do a different alternative and call my mother to let her bring the Id here, even then, the Id isn't that important. So, although i was talking to them in a calm manner and not showing any signs of rebellion, they had threatened to call the police on me without thinking twice before calling my parents. This is where i started getting angry, and even then now the black peers agree that could have been a racially motivated action. They then told me to sit in the office conference room because of that, leading into more anger. They had then called my mother who had came over to the school didn't even let ...
Post a Comment
Read more

TIFU by putting my already skinny jeans in the dryer on high heat.

TL;DR: Was stupid and didn't realize I put my clothes on extra high heat in the dryer. Had to rock skintight skinny jeans all day with tighty whities (only clean pair I had since I procrastinate doing laundry like crazy). I guess the constant wedgies and squishing are punishment for my stupidity. Honestly don’t know who else to blame but myself for this. I’m a scatterbrained guy so I literally put the highest setting on a load with most of my clothes, and my skinny jeans that I was planning to wear today. You can probably already see where this is going, but somehow I didn’t. For context, these jeans were already pushing the limits of what could reasonably be called wearable. They fit, technically, but only in the sense that I could get them on with enough determination and a bit of strategic breathing. Sitting down in them was more of a commitment than a casual action. Still, they looked good, and I had convinced myself that discomfort was just part of the aesthetic. So this m...
Post a Comment
Read more