I Went On Vacation With My Hookup & It Turned Out To Be A Huge Mistake

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"Let's go somewhere warm this weekend," Aaron* said to me one morning. I peeked my face out from under his sheet, duvet cover, and three fleece blankets. It was late February and approximately 8 degrees out all the time. That's the kind of weather that would make anyone do something ridiculous — like going on vacation with your hookup.

Aaron and I had been dating for two months. Well, maybe "dating" isn't the right word. Three nights a week, he'd invite me over to his scarily immaculate Brooklyn apartment. I'd linger at his kitchen counter, trying to look cute and tell cuter stories, while he made us cocktails in a silver martini shaker. Then, we'd change into bathing suits and have the drinks while soaking in his building's oversized indoor hot tub.

Aaron and I had easily agreed not to see other people. But he had also made it clear that I wasn't his girlfriend. "I'm 33 and not getting any younger. The next person I call my girlfriend is going to be the person I marry," he told me once. I was 23 and felt that the "buy six bikini waxes, get one free" deal at European Wax Center required a smidge too much commitment; marriage was not something that appealed to me then.

Still, I was smitten. On that frigid February morning, we brainstormed destinations and fantasized about tropical weather. A few hours later, when we were both at work, he texted me with a link to a decently priced flight he found going to Puerto Rico next weekend. We both bought tickets. He booked us a room at a resort.

I wondered if it was too soon to travel together, especially since we weren't even "officially" together. Aaron knew I wanted a real relationship, and I hoped he'd come around in time. I figured that if everything went well in Puerto Rico, it would just be a matter of time before he was ready to call me his girlfriend.

The trip started off fabulously. He snuck me into the VIP lounge at the airport to sample the all-you-can-eat cheese buffet and unlimited open bar. The flight attendant referred to me as his wife, and neither of us bothered to correct her. Our plane landed at midnight in San Juan, and by 1 a.m., we had shed our parkas and changed into shorts to go salsa dancing.

The next day, we ate steaming arepas from a food truck, drank mojitos at the resort's swim-up bar, and sunbathed on the beach. He even took selfies by the ocean with me. I privately hoped I could post one by the end of the trip; up until then, I hadn't posted anything about him on social media because we weren't "official." At night, we splurged on a gourmet meal at the kind of restaurant where every bite feels like your taste buds might explode out of pure joy. After dinner, we followed the noise of a crowd around the corner and discovered an open square filled with couples salsa dancing. We joined them. It was like the entire day had been executed flawlessly by the producers of The Bachelor. I felt like I was ready for my rose.

For breakfast the next morning, we visited an adorable café. There was a lull in the conversation — with Aaron, there were usually more lulls than I felt comfortable with. I filled the silence by commenting on how pretty the restaurant was and how happy I was to be on the trip with him. Aaron glanced up from his cappuccino.

Don't think that this trip means anything. I just wanted to get away for the weekend. And I happened to take you along.

"Don't think that this trip means anything," he said. "I just wanted to get away for the weekend. And I happened to take you along." He shrugged.

I felt so stupid.

So!

Stupid!

Up until that moment, I assumed this was a romantic getaway. I mean, our hotel's pool had a waterfall. I thought he was almost ready to ask me to be his girlfriend. Seriously, what kind of guy drops hundreds of dollars on a vacation for someone he doesn't even care that much about? The answer, of course, is a 30-something guy with money to burn who wants to spend a casual three days on a beach with a hot, young girl in a bikini. I should've seen this coming.

There were two more full days of our trip. I didn't want to ruin it. Maybe it could still be salvaged. So I didn't flinch.

"Right!" I responded brightly. "Yeah, of course. Same! I really wanted to get away for the weekend, too."

Instead of communicating why I was upset, like an adult might, I pretended everything was fine. Then, I ordered so many consecutive mojitos at the swim-up bar that I dropped one into the pool. I spent the afternoon in our hotel room asleep by myself. When I woke up, I quietly asked if he even liked me. His response — a defensive-sounding "yeah" — came a half-second too late.

I rallied. My plan was to look so ridiculously, disgustingly, devastatingly beautiful at dinner that he'd fall in love with me before the waiter could even take our order. I put on a white, off-the-shoulder crop top and a tight yellow skirt. I spritzed sea salt spray into my hair so I looked like a mermaid or a maybe an Instagram star. I wore the uncomfortable heels I knew he liked.

But my drunken nap had eaten up most of the day, and it was late now. Restaurants were starting to close. The minute we walked outside to find an open dinner spot, there was a torrential downpour. My outfit turned see-through in five seconds. We huddled underneath a stone archway as he scrolled carefully through Yelp, comparing restaurant reviews. I apologized for falling asleep earlier, and I begged him to pick a place. Any place. The longer we waited, the fewer restaurants would be open. (Also, we were basically underwater.) But he refused, citing the fact that he's a foodie and couldn't eat just anywhere.

We stood outside in the rain for 15 minutes. My platform sandals were waterlogged. We wound up at the hotel's Italian restaurant, paying $25 each for glorified spaghetti, and chewing in total silence.

When you're with the right person... All that matters is that you're together.

There were thunderstorms the next day. We couldn't go to the beach like we'd planned. If circumstances were different, the day could've been fun. When you're with the right person, you could do the most boring tasks imaginable and still have a great time. Fold laundry, do your taxes, watch paint dry, whatever. All that matters is that you're together. We clearly were not the right people for each other. When Aaron suggested we try switching to an earlier flight home, I agreed.

I knew the trip spelled disaster for our relationship, but I couldn't help but pick at our sore spots, the same way I'd pick at a scab. I felt frantic. On the flight home, I edited the selfies we had taken on the beach. There were two shots I liked.

"Do you mind if I post one of these? Maybe this one, or..." I asked, thumbing through my phone, heart racing. "This one?"

He shrugged again. "I think this all means more to you than it does to me. Do whatever you want," he said. But his tone of voice twisted the sentence so it sounded like, "I can't believe you actually care about Instagram, or selfies, or me! Don't post any of those pictures." I wound up posting a shot of the ocean instead.

You'd think that would've been the end for me and Aaron. It should've been. Instead, I kept seeing him for the next two months until he broke it off. I spent the rest of the spring and summer nursing my bruised ego and growing a backbone.

Before our trip, I had convinced myself that it was silly to worry so much about how Aaron and I had labeled our relationship. But my initial gut feeling was right: Labels guarantee that you're both on the same page. They offer security. His request to be "exclusive but not official" meant that he wanted all the perks of being my boyfriend but none of the responsibilities.

I wish I had respected my own desires as much as I had bent to his.

I had feared that pushing for a real relationship would make me look desperate. But it's hard to think of anything more desperate than me on that flight home, asking Aaron which couples' photo he liked best when we clearly weren't a couple in his mind. I should have been confident enough to ask him for what I wanted. I wish I had respected my own desires as much as I had bent to his.

I don't regret that vacation because it taught me to speak up for myself. The next time I met someone I wanted to be in a relationship with, I told him so — and he agreed.

* Name has been changed.

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