Unromantic Moments on Allegedly Romantic Vacations

I am not a romantic. To me, Valentine’s Day is only a convenient peg for a post. (But read till the end for an uplifting moment of “aww.”)

[Ed. note: These are all being posted anonymously because none of us want to own up to our romantic pasts.]

This one’s a bit long, but it’s one of my favorite stories told to me in any context at any time.

About ten years ago, the ideal vacation fell into my lap. A new coworker, Kristen, had a call from her father saying that he’d double-booked his time share and asking her if she could get away long enough to make use of the two-bedroom condo he had reserved in Kauai. Kristen’s mother was a flight attendant for United and flew for five cents a mile. She invited her boyfriend at the time, Ralph, and me and my boyfriend at the time, Eeyore.  Uh, a free place to stay on a tropical paradise and a cheap-ass flight to boot? Sold.

What I didn’t know at the time –but do now, thanks to the magic of hindsight—is that Eeyore and I were breaking up. Anyone who has gone through a breakup understands that there’s a tipping point; a point at which you know you are breaking up and the breakup is irreversible, even if the actual breakup occurs later. What most people don’t realize, however, is that there are months of quiet discontent leading up to this tipping point. We were at the very beginning of our Tropical Paradise of Discontent. We were breaking up and we didn’t even know it yet.

We were so excited about our trip. We talked about it constantly. It was our first big trip together. We flew to Kauai and met our first challenge immediately outside the airport.

We were not yet twenty-five, and no reputable place would rent a car. We found the name of a rent-a-wreck that let us rent a car in cash. This was the first of three cars we rented that week. That one leaked antifreeze. The third car had a tear in the tire that was primed to burst. The second car not only had a rusted out trunk (you could see the road), but it was infested with roaches. Eeyore called me “picky.” I have slept in train stations. I draw a line at roaches.

The second challenge we met with almost immediately was that I was the darkest complected of our bunch and the only one who managed to avoid getting sun poisoning after our first day at the beach. This meant that Kristen, Eeyore, and Ralph spent the remainder of their time recovering and avoiding the sun on our tropical paradise. When I wanted to go outside, I was told that I was “pouting.”

Third, Ralph was not yet twenty-one and could not legally drink, which meant that nightlife–already scarce—was nearly out of the question. No bar would let us in. There was little else to do after dark. Every night, they wanted to stay in the condo and play card/drinking games. I asked if we could, maybe, do something else. Now I was “bossy.”

Fourth, Kristen and Ralph slept until nearly noon every day. Eeyore and I got up around seven, but Eeyore felt that it would be rude to take the car while they slept and, oh, I don’t know, do anything other than sit around with our thumbs up our asses. When I brought this up, I got a lecture about how ungrateful I was for this wonderful vacation.

Last, Ralph one day went grocery shopping, met a not-schizophrenic homeless man, and offered him a place to stay. On our couch. With us. FOR THE REST OF THE WEEK. I WAS THE ONLY ONE WHO SEEMED TO HAVE ANY KIND OF AN ISSUE WITH THIS. I was summarily outvoted, and the homeless man took over the couch.

Let’s recap, shall we? This “wonderful vacation” consisted of a shit ton of crappy cars and a lot of sitting around inside. During the day, we sat around because everyone except me was feeling sunburnt and lousy. At night, we sat around because we couldn’t go out. And, when I suggested other things to do, I was told that I was being ungracious. When I voiced discontent at NOT WANTING TO MOVE A RANDOM HOMELESS PERSON IN WITH US ON OUR TRIP WHO COULD FOR ALL WE KNOW RAPE AND MURDER US, I was told that I was being uptight. Wonderful vacation my lily white, Chicago in February ass.

Looking back, it doesn’t surprise me that Eeyore and I broke up. What shocks me is that we stayed together for several months after that.

OK, that was pretty funny. This next one isn’t funny. It’s awful. That’s sometimes the way these things go.

It was our first winter as a for-real married couple, and we wanted to go someplace warm and romantic and relaxing. Puerto Vallarta it was. Upon arrival, however, my bipolar husband announced that he only had about one day’s worth of meds with him. He’d decided that he’d just buy some cheap drugs at the infamous and ubiquitous Mexican farmacias. On the third day, he went into town alone to obtain these pills while I laid on the beach, trying to actually enjoy our vacation. We agreed to meet up in town to have dinner. You can only imagine how well this worked out.

Instead of being able to find the medicine he was actually prescribed, he got a big box of muscle relaxants and another big box of anti-anxiety meds. And proceeded to pop pill after pill, washing them down with beers and tequila. When I reached the bar where we were supposed to meet, I immediately knew something was wrong. He couldn’t put two sentences together. The bartender was giving me deadly looks, like, “This guy is your problem, not mine. Get him out of my bar.”

I had to wrestle the boxes of meds away from him to figure out how much he had taken. The phrase “a fuckton” comes to mind. So I spent the next three hours arguing, fighting, and literally dragging my husband through the darkening and unfamiliar streets of Vallarta, trying to find a cab to take us back to our resort, fending off the other drunk people, and freaking out that the next time he passed out on me, he wasn’t going to wake up.

The worst bit, strangely, was once I’d flagged down a cab and shoved him into it. The whole ride back to the resort, the cabbie was joking with me about the fact that my husband couldn’t sit up straight and kept knocking his head on the window and the seat back, and I felt the need to keep up pleasant chatter while simultaneously pinching and slapping my husband to get him to react so I could be sure that he wasn’t dead yet.

(Obviously, he did not wind up dead. He woke up the next day massively sick and out of it. For reasons highly related to this story, we aren’t married anymore.)

Whew. Glad we made it through that one. Shifting gears a bit: This is not really the proposal scenario that most women dream of…

The worst “romantic” vacation I ever took happened with an ex-boyfriend, after we broke up.

I had been in a long-term relationship that really should have ended months before it actually did. By the time we had finally ended it, we had already booked a two-week trip to Australia, which was right around the corner. We decided it would be OK to still go on the trip, as friends. Come to find out, after we had broken up that he decided he was going to buy a ring and propose. I think he was going to take the opportunity in Australia to prove to me he’d changed and then pop the question.

Right before the trip, I found out about his plan and made it very clear that he should not even bring the ring on the trip.

Most of those two weeks were fine–we had a good time, saw a show at the Sydney Opera House, climbed the Harbour Bridge… We made good travel buddies.

It wasn’t until our last night of the trip, when he had booked a surprise gondola ride on the harbor, that I realized I was actually living my proposal without being proposed to.

It made for an incredibly awkward end to the trip and unknowingly put a ridiculous amount of pressure on whatever guy eventually will propose to me someday.

Moral of the story: Never, ever go on a romantic vacation with an ex.

Oof. Let’s close on a happier note, though. This one we’ll put a name to, since she’s got nothing to be ashamed of (in this particular instance)–this is the story of the honeymoon of our art director, Laura.

Jason had just started a new job when we got married, so we didn’t get a chance to take a real honeymoon. Instead, we went up to Milwaukee for a long weekend and had basically zero plans. We ended up accidentally eating at a chain restaurant (Rock Bottom Brewery) without realizing it wasn’t a local place, but had a lovely meal nonetheless. We asked our server where to go and what to do, and she suggested the Domes. Hanging out in greenhouses is a fantastic way to spend a winter afternoon, especially if you can park yourself on a bench and take a beer-induced nap. Later, we ended up going to a mall, which is more or less the most unromantic thing one can possibly do. But we splurged on fancy outfits for ourselves and wore them to dinner that night, at a restaurant that was puzzled at why we were so overdressed. The moral of the story is that any weekend can be, if not romantic, at least not unromantic if you just do a few things outside of your ordinary routine. And ask your servers for tips (and then tip them well).