TIFU by helping my friend’s proposal trip and losing the friendship instead

Fake names: Sally (me, 26F), my partner Dan (26M), my childhood best friend Daisy (27F), and her boyfriend Aaron (27M), who is now her fiancé.

This trip to Montreal had been planned in advance. Aaron secretly told us he intended to propose during the trip, and Dan and I were genuinely excited to help make it special.

Before the trip, Daisy and I spent a 2-3 long hangouts planning activities, meals, and budget. She apologized for the meticulous planning but I happily helped because she stated having a plan helped her feel comfortable, and I wanted the proposal trip to go smoothly.

Unfortunately, by the end of the week, I lost a friendship of over 20 years.

The first issue was at the grocery store where they wanted to split groceries with us to save money, yet restricted even the smallest of items unless it was approved by them. Dan was told to put items back on the shelf as if he was a child. We easily could have bought our own items. Daisy’s card failed after I already sent her my portion, and she had a meltdown when I explained she needed to send me back my money as well as the portion she now owed me. I gave her grace as she was very clearly overwhelmed. She realized at her own pace I was correct. No apology for lashing out. Just driving back in silence with a few excuses about her mood and stress.

When we arrived at the Airbnb, Daisy immediately called dibs on the largest bedroom. Not a huge deal. Nobody was entitled to it. Felt weird but I brushed it off. No biggie.

The listing looked cute online, with many positive reviews, and tactful photos. The reality was a small, cramped apartment that smelled like sewage, had drains that backed up (yeah, showers were fun with sewage to your ankles), and was 85°F even at night. I couldn’t help but poke fun at the landlord for each new thing we noticed was a lie in the post. I was suspicious of the reviews being paid or bots.

It was so damn hot. For multiple nights Dan and I couldn’t fall asleep. My body usually gave up consciousness around 2 or 3 AM after laying for hours.

There was a portable AC unit situated far down the hall from the bedrooms, and was terribly underpowered for the space. I suggested asking the host if we could move it somewhere more useful (2 screws held it onto the window opening) but Daisy refused because she wasn’t comfortable bothering the host. I expressed just how uncomfortable I was, and how 7 nights of this would really affect me. Worst case he would say no. She raised her voice and was very agitated. She got loud again and told me I should call myself if I wanted to so badly. (She was aware I could not use the messaging system which was only available to her via the app). She got worked up, went to the bedroom to isolate herself, Aaron entered to check on her and talk her through it?, and they both reemerged 10 minutes later like nothing happened. It was creepy like the twilight zone. It seemed to me like she cared about this landlord’s opinion of her more than us. Which was very uncomfortable to realize. We later requested a trip to the store for a fan, but ended up walking ourselves 40 minutes to grab a fan and thermometer. She insisted we were wrong about how hot it was and the thermometer is the only ounce of sanity I could provide myself. I knew I wasn’t crazy.

And we continued our day. Later, in a cafe, I returned to the table after ordering a cool drink when Daisy handed me her phone and demanded I put my card information in. I asked what for and she answered very impatiently it was for swan boats. It irritated her that I dared to ask what I was paying for and participating in. I was shocked and complied quietly, while something in me festered. There was no discussion. Just an expectation that I would hand over my card and fall in line. And I did.

It hurts realizing someone I respected and cared about had no respect or care for me.  I began to wonder what I was providing in this trip other than helping them afford the apartment, groceries, and gas. I realized we probably just a tool to subsidize their vaca. Each event made it clear this friendship was decaying rapidly with slim chance of survival.

The key situation didn’t help.

There was only one key to the Airbnb. Daisy and Aaron had the car, but also insisted they wanted to keep the apartment key at all times while they visited art museums. Dan and I suggested simply trading it back and forth depending on who was closer to the apartment, but that was immediately shut down. Daisy explained it was not fair or right to lock them out of the apartment, and she couldn’t believe we would do that to them.

The result was that whenever our plans differed, Dan and I had two options: be locked inside the apartment or be locked outside of it. It was a helpless and infuriating feeling. Especially on such a hot, sunny day. And being in a tourist spot with panhandlers and odd sorts of people about. It would be nice to have a place to feel safe or cool down when needed.

After a heated call, we decided to all meet up at the apartment to hash it out. We returned to find the host standing outside with two strangers. He claimed he was showing the apartment to potential buyers and also claimed attempts to contact us. None of us had been contacted in any way.

We were immediately creeped out he was prepared to enter the property with strangers while all of our belongings were inside, and with no notice. Airbnb agreed the situation was inappropriate and moved us to a different property.

What frustrated me was that suddenly every complaint I’d been making for days was valid. In the car ride home they bitched about everything that was formerly invisible:

Now the heat was a problem.

Now the smells were a problem.

Now the apartment was terrible.

Now the landlord was a slumlord and a jerk.

For days I felt like Dan and I were difficult for being uncomfortable. The second the hosts became the villain, suddenly everyone agreed.

So anyway. We move forward. New place. New day. Proposal happens and we are all in better spirits. For a brief moment I genuinely thought the rest of the trip might recover.

It didn’t.

The new Airbnb was objectively much nicer. The old problems were gone, but the tension wasn’t.

One of the first things that happened after we arrived was that I jokingly flopped onto the larger bed and dramatically announced, “Dibs, sorry guys.”

I expected maybe some laughter or joking. But Aaron immediately responded, “Really, Sally?”

The tone hit me hard. It sounded like “Why would you think that you would deserve that, and are you really going to be difficult with us?”

The joke lasted maybe two seconds before I didn’t feel like joking anymore. The thought of us being in it was a ridiculous idea to them. I actually didn’t want the room but I was being petty. I wanted them to have a second to feel how the other end felt and poke fun towards it. In fact, after the proposal, I thought it was obvious they should get the nicer room. The intention was to say “just kidding” and tease them a little bit before allowing them to enjoy the privileges of being newly engaged.

What bothered me was realizing they seemed to think so little of us. We looked at train tickets that night but I convinced Dan it would be cheaper to stick out that final day for the communal drive home.

The breaking point came on the final day.

A simple discussion about departure times somehow escalated into a full argument. Screaming included. Not from me. Absolutely ridiculous and silly argument about bagels. Afterwards, Dan and I escaped to cool off and I finally confronted Daisy through text about everything that had been building up throughout the week.

Her response stunned me.

She claimed she had no idea I was unhappy.

She claimed I had never communicated my concerns.

She claimed Dan and I had spent the entire trip pretending everything was fine.

When I reminded her about the conversations we’d had throughout the week regarding the apartment, the key, and everything else, she repeatedly accused me of gaslighting her.

The conversation moved from text messages to phone calls and back again.

Every issue seemed to be denied, minimized, rewritten, or blamed on me.

Eventually Dan found screenshots in our group chat that directly contradicted one of the things she was claiming had happened.

I sent the screenshot.

There was a long silence.

Then she said, “We’re leaving tonight.”

That was it.

At that point Dan and I no longer felt comfortable traveling home with them. We arranged our own transportation back across the Canadian border and spent the remainder of the trip separately.

As a final insult, they threw away a bag containing all of my dirty clothes immediately before leaving. Everything I had worn through the week. Favorite shirts, pants, bras, etc. Aaron apologized at least while Daisy made no peep over the phone.

I considered rescuing them until I went out back and discovered a raccoon guarding the dumpster like he paid rent there. I decided he could keep them. The rabies was not worth it, nor was the cost of rabies shots.

So I came home having spent a week of PTO on one of the most stressful vacations of my life, losing a friendship I’d had since elementary school, and losing the mutual friendships attached to it as well. And my damn clothes.

TL;DR: Helped my best friend’s boyfriend plan a surprise proposal during a week-long Montreal vacation. A terrible Airbnb, multiple sleepless nights, growing tension, and a friendship-ending argument resulted in my partner and I finding our own way home across the Canadian border. The proposal succeeded. The friendship didn’t.