"Uh oh, you're a runner?" he asks me.
"Haha are you scared?" I respond.
"Runners are serious!" he says. "I've never seen someone smiling while running."
"But does anyone really smile when they're working out?" I point out.
I'm texting with Ray, a 28-year-old who works in Occupational Safety in Alaska. We'll be meeting for the first time in about a week in Portland, Oregon, a place neither of us have been, and I'm trying to convince him I'm not a serious person. Ray and I were set up by MissTravel, a dating site for travel-seeking singles. We’ve been getting to know each other and have texted here and there for the last month leading up to our trip that the site arranged for us. Earlier this year, the site approached me and asked if I wanted a first-hand account of what it’s like to travel hundreds of miles for a first date with one of their members. I asked zero questions because um, hell yeah, take me anywhere!
I picked Ray from a selection of five MissTravel members. The site described him as "witty, calm and enjoys intelligent conversation and hearing different viewpoints." They emailed me two pictures of him, a link to his Facebook, and then I got my flight confirmation.
Before We Met
After I picked Ray as my date, they gave me his email and phone number. It may have been a weird time to start chatting, because we wouldn't be meeting for another month, but I figured I should at least confirm my life wasn't in danger in case people asked.
That set the tone for the rest of our text conversations until we met: light, fun, and able to joke about being serial killers. I've never written about a date before, just my dating life in general, and he knew I'd be writing an article from the beginning, so it was an unusual situation right off the bat. Will this be a date? Is it for an article? A little bit of both? As you'd imagine, I come across these questions a lot as a Sex and Relationships Editor — and I rarely know the answers.
Ray agreed it was a strange dynamic, so I made it clear I wasn't going to interview him and that anything I asked would be coming from someone he's away for a weekend with, not someone writing about it.
We agreed not to make any plans for Portland. I asked some co-workers and friends for their recommendations so we had some ideas of things to do there, but I was relieved to hear we wouldn't have any sort of itinerary. Ray had asked me if I was a planner while we were texting and initially I said that I was, but I meant it more about my life in New York, which tends to be pretty routine-like. On vacation, it's totally different. In fact, at the time I answered his question, I was on a six-day trip where I had made zero plans.
When they were casting guys for my trip companion, MissTravel asked me about my date preferences. Not totally sure what they meant, I used it as an opportunity to send an overly detailed description of who I was (energetic, independent, impulsive) and what I was looking for (James Franco > Channing Tatum, funny, fun).
Reading it back now, it makes me cringe. It reads like a checklist. It also says I'm "definitely looking for something serious", which was certainly not my expectation for a weekend trip and isn't even entirely true. I said that in my bio as more of a defense mechanism, which I think a lot of us do online because it's an easy way to weed out those who aren't just looking for hookups but are actually expecting them — something I've encountered in New York a lot.
While I'm probably more open to a relationship at this point in my life than I was a year or two ago, it's not really something I've been actively seeking. I think that's a hard concept for a lot of people to understand about a single 28-year-old woman. I like things to happen organically and I need to take my time. There's nothing worse than feeling pressured or rushed.
About The Site
I had heard of MissTravel before. I knew that people on the site traveled together, either to new locations or to one person's city to meet up, and that you could choose who paid: you, them, or split the costs 50/50. I had even read about a girl who quit school and used the site to travel/date around the world. It sounded risky, but also kind of exciting. An "Escorts are not welcome" disclaimer appears at the bottom of several of the site's pages. I had never seen a note like this on a dating app or site, so it had me wondering who was using the site and what they were using it for.
If it was primarily a hookup site, wouldn't that be a bit of an expensive hookup? Why wouldn't you just go to a bar in your city? If it were a site for serious dating, wouldn't that be setting yourself up for a long-distance relationship? Why wouldn't you try Match? I wasn't sure what the ideal set-up would be on here.
Ray cleared up a lot of this for me before we met. He's used the site a couple of times and explained that it can really be whatever you want it be. The distinguishing factor here is that everyone loves to travel and is down to book a trip. He said there are some people on the site who want to go to pretty places and take Instagram pictures. Others live in the middle of nowhere and want to see the world but don't have the means, which is where someone else paying for the trip comes in.
You can send other members trip proposals, where you choose a location, dates, who'll pay, and the type of trip you have in mind: Luxury, Adventure, Romance, Foodie, Local. Members can then reject or accept trip proposals. The site has 615,470 members worldwide and is available in more than 135 countries — and 40 percent of MissTravel members live in the United States.
Ray looks at it as less of a dating site and more as a way to find a friend who's also interested in traveling, which makes perfect sense because he works in Alaska for two weeks at a time and then has two weeks off where he's free for adventures. OK, so more companionship versus romantic intentions, but it seemed like he's typically open to seeing what direction it goes in.
I love the idea of finding a travel buddy and booking a fun trip, but how do you know you'll be safe? Members are encouraged to get background checks and the site recommends members only go on trips with those who are background checked, Hannahmae Dela Cruz, MissTravel's PR Representative tells me. "Background checks are available for $25 for females and $50 for males," she says. "Once members obtain a background check, they get a badge on their profile."
Going into this, I was probably worried less about safety and more about awkwardness with a stranger.
Expectations
My text impressions of Ray pre-Portland: Good sense of humor, curious, goes with the flow, honest, adventurous, not a fan of runners, potentially scared of me.
My friends' reactions went like this:
"You're going to die."
“WHAT? You would.”
“That's a little risky. And too crazy.”
"Sex marathon."
"You're going to fall in love."
I had no idea what the weekend would be like. We were two strangers spending a lot of time together in a new city. My only goals were to explore, relax, and have a good time. I was excited to meet Ray, and I was hoping we'd get along, but I didn't know what our rapport would be like. We had textual chemistry, but I knew the weekend could go in so many different directions. So I signed into my account on my roommate's Find My iPhone and packed some condoms to be safe for all potential circumstances.
While I had no predictions for the weekend (or beyond), Ray had thought out all the possible scenarios: if we did hit it off, we could visit each other, if we didn't, we'd just have a crazy weekend, or if we got along but didn't feel any strong emotions, we'd hug, say "nice to meet you", and become LinkedIn friends. It all sounded reasonable to me but I thought it was kind of funny to discuss these trajectories before we even met. Maybe this is something you have to make clear before meeting a travel companion? It made me wonder why he was on board for the trip and if he was nervous about my expectations for the weekend.
As our meeting day got closer, I started to get nervous, partially because of the petrified look on my parents' faces when I told them I was heading to Portland with someone I've never met. I also know how long it can take me to feel comfortable with a new person. Sometimes it happens quickly, but more often than not, it takes me time. The last few guys I've gone out with in New York were great initially but became too aggressive by the end of the date.
I did my best to remember that Ray seemed chill, funny, and had already been checking in to make sure I wasn't worried about our weekend.
Getting To Portland
Ray and I were supposed to meet on Friday afternoon in the Portland airport, but I missed my connecting flight and ended up spending an extra four hours at the Denver airport. My close friend Natalie, who lives in Denver and is both sensible and adventurous, met me at a brewery in the airport. She eased my nerves and told me Ray sounded like a "great, Midwestern guy."
When I landed in Portland, I took a ride in a friendly (and eco-friendly) taxi who brought me on the scenic route, pointing out each and every recreational weed shop along the way to the Jupiter Hotel, the revamped motor inn-turned-boutique hotel we were staying at. The guy at the front desk asked if I was in Portland for business or pleasure. I said I really had no clue and explained why I was there. "OMG! This sounds like the beginning of a romantic comedy!" another woman behind the desk said. I laughed, grabbed an apple from the bowl, and made my way up to my room.
First Impressions:
I first met Ray when he stopped by my hotel room, which was two doors down from his. Holy sh*t, he is hot. Tall (*praise hands emoji*). Midwestern (or is it Southern?) accent. I dig it.
My best friend checked in and I responded quickly, with spelling errors, as one does when they're in the first few moments of meeting the stranger they're spending the weekend with and trying not to pay too much attention to their phone:
Day 1:
Ray doesn't jaywalk. I noticed this right away because I'm an impatient speed-walker. Ray works in safety, so it makes sense he's cautious, but I made him jaywalk with me a few times and he was cool about it. A couple of minutes into our walk around Portland, he took note of how I don't really pay attention to street lights and that I sometimes veer off the sidewalk, and he switched places with me so I wasn't near the street. I quickly nicknamed him "Mr. Safety."
Ray's personality was similar to what I had imagined, but there are so many things you can't tell from a person's words and emoji. We all have perceptions of ourselves and ways we want to appear to new people, but that's not always how we are face-to-face. For example, he was a little more serious than I expected — still with a great sense of humor — but I didn't pick up on how introspective he was via text. I remembered his bio said he was calm, but again, that's more of a vibe that you get from him IRL.
Ray was easygoing. I knew this when we were texting, and it was something that made me excited to meet him, but seeing it in person was really refreshing. When I became single for the first time in a long time a few years ago, it was the point of my life where I really learned how to go with the flow. I stopped trying to control things around me, stopped planning things out, and started embracing change. I became more outgoing, less rigid, and a bit fearless — at least enough to go meet a stranger in Portland for the weekend. I knew our mutual interest in winging it would work well for us.
After exploring Portland for a bit, we stopped at local brewery Burnside Brewing Company and went back to the hotel to watch Insane Pools and chat. We called it a night and Ray went back to his room. I felt more comfortable with Ray than I did a few weeks ago when I had drinks with a guy who went to my college and had about 15 friends in common with.
Talking to Ray was easy, really easy. I quickly forgot our situation.
Day 2:
The next day, we Ubered to the airport so we could rent a car and explore the Columbia River Gorge Waterfalls. "So what brings you to Portland?" our driver asked. The right words weren't making their way out of my giggle fit, so Ray took that one.
We got our car, went to McDonald's, where I had my very first Egg McMuffin, and hit the road. We stopped at one of the waterfalls and took some pictures of scenery that looked like it was straight out of Twilight, which Ray told me he watches with his mom.
We decided to drive down to Cannon Beach next. During the two-hour car ride to the coast, we sang along to Sugar Ray, Incubus, and All-American Rejects, and rated Taylor Swift's new song that neither of us had heard before (we didn't like it). We talked about our families, growing up, him in Oklahoma and me in New York, and dating.
I told him how I was frustrated with pushy guys and how much of a turn-off it is to have someone you hit it off with get bent out of shape when you don't go home with them. He explained he genuinely doesn't expect anything from the women he meets on MissTravel. Ray doesn't seem to have expectations about things in general. He's not a planner. His life is exciting, and he's grateful for it. He's going to move in May, and he has no idea where he'll go yet.
When we got to Cannon Beach, we stopped at a state park and walked along a few trails that we thought might lead us to the beach, but didn't. Instead we got pretty views, good photo ops, and a serious laugh when I slid in slow mo and did a split in the mud. Ray is courteous, but he stood back, laughed, and took a picture as I sunk further into the mud. Note: Perforated leather slip-ons are not hiking boots.
We decided to ditch the park and head down to the beach even though it was starting to pour. I was ready to make a run for it and play in the rain but Ray seemed hesitant. I said it was fine if we didn't go and he said I was supposed to convince him.
I had to remind myself I wasn't hanging out with an assertive East Coaster and I hated that it's what I've become accustomed to. I told him we were going outside. We skipped along the beach, which reminded him of Rocky and me of Coldplay's "Yellow" music video. We even ran a bit on the flat sand, where I made an effort to smile even though he couldn't see my face. We took some pictures and laughed at how some of the rocks in the water looked like penises.
My friends checked in, and once again, I responded like a drunk person.
I texted my dad that my phone was dying but not to worry because everything was totally fine and he responded with a crying emoji. We drove back to Portland, got ready, and went to dinner. Watching a guy who was alone at a table drinking a beer by himself, Ray joked that the guy was him because he likes doing things alone. We made guesses about who the guy would try to pick up. But then I spotted the guy's wedding ring.
Before going back to my hotel room, we went to a bar where we laughed at some of the characters there and did gross tequila shots. At one point while we were lying in my bed, he asked me what I was thinking. Out of fear of making him uncomfortable, I didn't say what I really thinking, which was that I wanted him to kiss me. (The last time I made the first move, I was in eighth grade and I found out the guy was gay a few months later.) Ray had made such an effort to make sure I was feeling comfortable that I didn't want to risk it.
Day 3:
We headed to the airport early in the morning and had breakfast at an eclectic beach-themed restaurant at 7 a.m.. We laughed at our waitress who seemed as though she was about five and a half Red Bulls deep. A weekend sounds like a lot of time to spend with someone you've never met, but I felt like it was too short at this point. I wasn't really thinking about how we'd say goodbye or what would happen next.
Ray's flight was before mine so he finished up eating quickly, hugged me, and said it was nice meeting me. I had a flashback to the three outcomes he laid out before we met. And then the next morning, I got a LinkedIn request from him.
Afterthoughts:
Ray was interesting, funny, and went out of his way to make me feel comfortable. I wasn't afraid of him seeing my clumsiness, how awful I am at navigating directions in the passenger seat, or whether he'd judge me for ordering a salad like guys in New York do.
When you travel with a significant other for the first time, it can make or break your relationship. It usually doesn't happen until several months down the road, and it's often thought of the time where people’s “true” selves are revealed. But when you travel to a new place with someone you don't know, it’s like an alternate reality — you may let your guard down, have deep conversations, and heightened emotions, but how real is it? I think it's something you probably figure out in time.
Traveling over 2,000 miles did feel worth it for a fun weekend. And depending on how you feel about long-distance relationships and whether you have the means, I do think this could be a viable way to meet someone.
Everyone asked me if I was ~in love~ when I came back to New York. Even the guy next to me on the plane, who was fascinated by my weekend, wondered. Yes, that would make a good story, but no, I am not in love. I spent a fun 41 hours in a new city with someone I just met.
I don't know if we'll see each other again. He seemed pretty great, but I know less than two days-worth of him and vice versa. As he's pointed out, we're both busy people. So maybe we'll keep in touch and just go with the flow.
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