I Went On A 48-Hour Staycation Date With A Stranger

After traveling 2,737 miles last March for a date through MissTravel, the dating site for travel-seeking singles, I was pleasantly surprised by how the weekend turned out — surprised over the lack of awkward silences, surprised that a three-day first date felt short, and ultimately, surprised by how easy it was to let my guard down around a stranger. I returned home elated over the adventurous weekend — but confused about whether my feelings toward my date were real, or whether I was just caught up in the fantasy of vacationing with a hot stranger far away from home. I hoped to see him again and was bummed when he wasn't trying to follow up. For him, these weekends weren't so rare, and he knew how to be realistic about them. We texted for about another month, until the conversation faded. Still, the experience was eye-opening.

So when the same dating site asked if they could arrange another date with one of their members for me, this time where one person hosts the other in their city, I thought... why not? I'm starting to enjoy taking risks for the sake of my dating life, which exists somewhere between my job, texts, and bars in lower Manhattan. Maybe this next "trip," which would be in my city, New York, for 48 hours, would be a little easier now that I'm familiar with the territory.

MissTravel allows users to send trip offers — you can meet up in a new location and travel together, have someone visit you, or visit someone in their hometown — and decide who pays, or if you'll split the costs 50/50 ahead of time. Sure, there's a risk involved, but perhaps the most important part of the site is where you indicate what you're looking for. Knowing someone's intentions is key in this situation.

Friends expressed concern. What if you're dating someone then? Could this be holding you back? I went into my first MissTravel experience as a dating app-aholic, bored with NYC guys, and ready for something different. I deleted my dating apps for a few months — and I went on better dates. An ex who I'd been struggling to get over for what feels like eternity popped back into the picture for a bit — and then got back together with his girlfriend, throwing me for a confusing, regressive loop. Bored and admittedly a little closed off, I ignored my well-intentioned friends and agreed to another weekend with a stranger.

Before The Trip:

Since I'd be writing about it, the site sent me a couple members to choose from, all of whom were OK with that. I chose Tom*, an entrepreneur from California. (Normally you browse the site and message members.) I thought he looked cute in his pictures, but I mainly picked him because he seemed like someone I could get along with effortlessly. He was described as family-oriented and a good mix of a typical New Yorker and a laid-back LA guy. We started speaking about two weeks before the trip, which left me no time to make assumptions or cyberstalk him. At the same time, I had no idea who I was about to spend 48 hours with.

I gathered this from our brief text exchange: Tom was easygoing (he was down for all my suggestions), light-hearted (see train joke above), and loved NYC (he was born here). The fact that he was willing to fly across the country for a date with a stranger and have me write about it led me to believe he'd be a good partner-in-fun for a weekend. Hopefully he'd be on the same page. I went into the 48-hour staycation not too worried, but determined to show a visitor a good time.

Day 1:

We first met in the lobby of the Refinery Hotel where we both stayed for the weekend (on different floors). I wasn't nervous — since I was more interested in making a friend out of this than anything else, that undoubtedly took pressure off. Tom had dark features, some scruff, and wasn't kidding when he told me about his orange-ish hair.

He was handsome, but I didn't feel an instant attraction to him. That didn't worry me — I was still excited to get to know him. He seemed a bit low-energy initially (which was understandable since he had arrived at 1 a.m.), but once he had some caffeine, he perked up. 

Tom said he hadn't traveled with anyone from MissTravel, but he'd hosted out-of-towners and met up with people in LA. When he hosted someone from London for seven days, it started off great, but as the novelty wore off, he felt like he was living with a girlfriend who he hardly knew. When she left, he said it seemed like she thought there would be potential for something more, but she then realized it wasn't realistic. I flashed back to riding the high after my first MissTravel date, thinking it was totally possible to keep in touch and meet up with someone who I hardly knew again on the other side of the country.

When the sun started to set, we went to the Refinery Rooftop, where the happy hour scene bustled with people our age — mostly women coming from work. Over dinner and drinks, we discussed how much we despise dinner dates. I wasn't sure if this was a date. We wouldn't have been there if we weren't single, but it wasn't too flirty. It felt refreshing that neither of us attempted to cross the line. It was nice to have that choice without the pressure you feel on a first date to find chemistry instantly. At this point, I was considering Tom my frate, aka my friend-date.

Somewhere in-between discussing our signs (he's a Taurus, I'm an Aries), The Five Love Languages (I'm Words of Affirmation and Tom thinks he's Acts of Service but hasn't taken the quiz yet), Tom hesitated and then told me about something pretty personal he was going through. I'd known Tom for about eight hours at this point, but I really felt for him.

On a first date, it would've felt like too much information, but on our date, it felt fitting and I was happy he shared it. The dating scene is unforgiving — just one weird tweet from 2012 or a text at the wrong hour and you could be out.

We finished our drinks and met my friend Lindsey and a guy she was seeing, Jeff, at The Happiest Hour. I wondered if our rapport would change once we got to an energetic bar with two people who were on a date. When we walked in, I barely introduced Tom before he jumped right in. I admired his confidence.

Later that night, we parted ways when the elevator stopped on his floor. I didn't anticipate him trying to kiss me or invite me to his room, because things felt comfortably platonic. I was curious if things would become more flirty the next day, even though it wasn't my in intention. The way it was at this point was uncomplicated, and I liked that. I needed that.

Day 2:

We started off with brunch at Parker and Quinn, testing out their Bloody Mary Board, complete with olives, pickles, and bacon. As we waited for our food, we ranked our favorite berries and talked about coffee — much to the delight of the woman next to us who worked for a coldbrew company and promised us samples. Next, we walked to a spacious rooftop for my friend's birthday party.

Tom was about to meet my childhood friends, but I didn't sense any hesitation from him. As outgoing as I can be, I'd be intimated if the situation were reversed. I mean, I was slightly nervous. Usually, when I introduce someone to friends, it's a make-or-break moment — not just because of what my friends think, but because it also reveals how really feel about the guy. Am I anxious? Afraid what they might say? Annoyed they aren't engaging in conversations? But on this day, I was bringing someone I met 24 hours ago, who felt like more of a friend than a date, so I wasn't sure what to expect.

Tom was a great sport, initiating conversations, joining our group photo, and answering questions from curious friends. I quickly relaxed. His cousin came by, and then a bunch of us went to dinner. At that point, Tom even attempted to change his flight so he could stay longer. I wasn't sure why, because I wasn't getting flirty vibes from him, but I wondered about his intentions. I'd be going to my parents' the next day, so I wouldn't even be around. Maybe he wanted more time with his cousin. Either way, I still felt good with how things were going. I wasn't feeling a spark, but I still enjoyed his company.

Next, we had a dance party in my hotel room, which was bigger than my apartment and felt like a Lower East Side art gallery. My friends asked if I thought we'd kiss that night. I said I didn't know, but probably not. I enjoyed that things were platonic.

Tom and I left my friends drinking wine and dancing on the bed and went to Winne's, a prohibiton-era bar in the lobby of the Refinery. We sat on comfy chairs, ordered classy cocktails, and talked about online dating as a jazz band played next to us. I played around on his J-Swipe a few times, adding a little modern day flair to the old-time New York atmosphere.

Later, we met his cousin and my friends downtown and danced for the rest of night. I laughed to myself as I watched Tom, who was a total stranger two days ago, sit across from my best friend and give her dating advice at 3 a.m. It seemed like we were on the same page still, but there was always the chance though that he was thinking something different. Part of me feared rejecting him if that were the case — we had just spent the last two days together and everything was so easy. I didn't want to hurt his feelings.

Luckily, it didn't come to that. Tom had an early flight, so we said goodbye with a hug in the elevator at his floor again. He said he'd return the favor if I ever came to LA, and I think I'll take him up on that.

My Final Thoughts:

Tom had a good energy and enthusiastically went with the flow. Again, baffled by how much more at ease I feel during 48-hour weekends with strangers than on three-hour dates with friends-of-friends, I was able to be myself and have a good time.

Since you know you'll be spending an extended amount of time together, you make more of an effort to be on your best behavior — but I think you're also less likely to make quick judgments for that same reason. You can talk about exes, religion, sex, politics, personal struggles — all the things you've been instructed "not" to discuss with someone you've just met. You listen more and you have the opportunity to go substantially deeper.

Ultimately, I didn't feel a connection, but that felt like a relief. Even though I think we were on the same page, it made me realize something about rejection: It's easy for me to reject the guys who come on too strong or make me feel uncomfortable, but the idea of potentially having to reject a sweet, fun guy when you're just not feeling it? That feels a million times harder.

While the weekend didn't get me out of my dating slump, and I still feel emotionally unavailable, it was a distraction and a good reminder that is possible to spend time with someone and not feel an immense amount of pressure.

Dating in New York often feels like speed dating — you feel forced to make a decision about someone ASAP, which can take the fun out of meeting new people. Even if nothing romantic came out of this, I ended the weekend pleased with how easy it was to talk to Tom, and how much fun we had. And maybe that's exactly how a first date should end.

*Name has been changed

Images: MissTravel; Michelle Toglia

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