"Oooh, are you a runner?" he asked me.
"Haha, are you scared?" I responded.
"Runners are serious!" he said. “I’ve never seen anyone smile while running.”
"But does anyone actually smile while working out?" I pointed out.
I'm texting Ray, a 28-year-old who works for the Department of Occupational Safety in Alaska. We were meeting for the first time in about a week in Portland, Oregon, a place neither of us had been to and I was trying to convince him that I wasn't a serious person. Ray and I were founded by MissTravel, a dating site for singles looking to travel. We had gotten to know each other and spent the last month texting here and there before the trip the website arranged for us. Earlier this year, the site approached me and asked if I wanted a first-hand account of what it was like to travel hundreds of miles for a first date with one of their members. I asked zero questions because well, gosh, take me anywhere!
I selected Ray from among the five members of MissTravel. The website describes him as "witty, calm, and enjoys intelligent conversation and hearing different perspectives." They emailed me two pictures of him and his Facebook link, and I received the flight confirmation.
before we met
After I selected Ray as my date, they gave me his email and phone number. It might be an odd time to start chatting now since we still have a month until we meet, but I figured I should at least confirm that my life is not in danger in case people ask.
This set the tone for the rest of the text conversation before we met: relaxed, fun, and able to joke about being a serial killer. I had never written about dating before, just about my dating life, and he knew from the beginning that I would write an article, so it was an unusual situation. Will this be a date? Is it for an article? A little bit of both? As you can imagine, as a sex and relationships editor, I get these questions all the time—but I rarely know the answers.
Ray agreed that it was a weird dynamic, so I made it clear that I would not be interviewing him, and that any questions I asked would come from the people he spent the weekend with, not the people writing this article.
We agreed not to make any plans for Portland. I asked some colleagues and friends for their recommendations so we would have some ideas of things to do there, but I was relieved to learn that we wouldn't have any itinerary. When we were texting, Ray asked me if I was a planner, and initially I said yes, but I meant it more in reference to my life in New York, which tends to be very routine. On vacation, things are completely different. In fact, when I answered his question, I was on a six-day trip with zero plans.
MissTravel asked me about my dating preferences when they were selecting men for my travel companions. Not quite 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 , interesting, interesting).
Reading it back now, it gives me the creeps. It reads like a checklist. It also said I was "definitely looking for something serious," which certainly wasn't what I expected from a weekend trip, and wasn't even entirely true. I said in my bio that this is more of a defense mechanism and I think a lot of us do it online because it's an easy way to weed out people who are not just looking for a hookup, but actually Looking for a hookup - I encounter this a lot in New York.
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 something I've been actively seeking. I think for a lot of people, that's a hard concept to grasp as a 28-year-old single woman. I like things to happen organically and I need to take my time. There's nothing worse than feeling stressed or rushed.
About this website
I've heard of MissTravel before. I know people on the site travel together, either to new locations or to meet in one's city, and you can choose who pays: you, them, or split the cost 50/50. I even read a story about a girl who dropped out of school and used the site to travel around the world/date. It sounds adventurous, but also a bit exciting. The "Escorts Not Welcome" disclaimer appears at the bottom of several pages on the site. I've never seen a note like this on a dating app or website, so it makes me wonder who is using the site and what they are using it for.
If it's primarily a hookup site, isn't that a bit pricey for hookups? Why don't you go to a bar in your city? If it's a serious dating site, isn't that setting yourself up for a long-distance relationship? Why don't you try matching? I'm not sure what the ideal setup is here.
Ray clarified a lot of things for me before we met. He has used the site a few times and explained that it really can be anything you want it to be. The significant factor here is that everyone loves to travel and is willing to book a trip. He said some people on the site want to go to beautiful places and take pictures on Instagram. Others live in remote places and want to see the world but don't have the means, which is why others pay for the trip.
You can send travel suggestions to other members, where you can choose the location, dates, payee, and the type of trip you want: luxury, adventure, romance, gourmet, local. Members can then reject or accept the travel recommendation. The site has 615,470 members worldwide, covering more than 135 countries/regions, with 40% of MissTravel members living in the United States.
Ray sees it not so much as a dating site but as a way to find friends who are also interested in traveling, which makes perfect sense since he works in Alaska for two weeks at a time and then has two weeks off , can move freely. adventure. Well, more of a companionship than a romantic intention, but he seems generally willing to see where things go.
I love the idea of finding travel companions and booking a fun trip, but how do you know you'll be safe? Hannahmae Dela Cruz, PR representative for MissTravel, told me that members are encouraged to conduct background checks, and the site recommends that members only travel with people who have passed background checks. "The background check costs $25 for women and $50 for men," she said. “Once a member gets their background check, they get a badge on their profile.”
Having said that, I may be less worried about safety and more worried about the awkwardness of getting along with strangers.
expect
My impression of Ray before Portland: great sense of humor, curious, go-with-the-flow, honest, adventurous, not a runner, probably intimidated by me.
My friend's reaction was this:
"You're going to die."
"What? You do."
"It's a little risky. And it's crazy."
"Sex marathon."
"You'll fall in love."
I don’t know what the weekend will be like. We were two strangers spending a lot of time together in a new city. My only goals are to explore, relax and have a good time. I'm happy to meet Ray and I hope we get along well, but I don't know what our relationship will be like. There was chemistry between us, but I knew this weekend could go in a lot of different directions. So I logged into my account on my roommate's Find My iPhone and packed some condoms to make sure I was safe in every possible situation.
While I don't have any predictions for the weekend (or beyond), Ray has thought of all the possible scenarios: If we hit it off, we could visit each other, if we don't, we'll have a crazy weekend, or, if we get along Being nice but not feeling any strong emotions, we hug, say "nice to meet you" and become LinkedIn friends. That sounds reasonable to me, but I thought it would be kind of interesting to discuss these trajectories before we met. Maybe this is something you have to figure out before meeting your travel companions? It made me wonder why he was taking this trip and if he was nervous about my expectations for the weekend.
As the day drew closer for us to meet, I started to get nervous, in part because of the stunned looks on my parents' faces when I told them I was heading to Portland with someone I'd never met. I also know how long it takes for me to feel comfortable with a new person. Sometimes it happens quickly, but more often than not, it takes my time. The last few guys I dated in New York were initially great but became too pushy by the end of the date.
I tried to remember that Ray seemed calm, fun, and had checked in to make sure I wasn't worried about our weekend.
Travel to Portland
Ray and I were scheduled to meet at the Portland airport on Friday afternoon, but I missed my connecting flight and ended up spending an extra four hours in the Denver airport. My good friend Natalie, who lives in Denver and is both sane and adventurous, met me at a brewery in the airport. She eased my nerves and told me that Ray sounded like a "great Midwesterner."
When I landed in Portland, I caught a friendly (and eco-friendly) taxi that took me on a scenic route and pointed out every casual weed shop along the way to the Jupiter Hotel ( Jupiter Hotel's converted motel. -The boutique hotel where we stayed. The person at the front desk asked me if I was in Portland for business or pleasure. I said I really didn't know and explained why I was there. "Oh my gosh! This sounds like the beginning of a romantic comedy!" said another woman behind the desk. I smiled, grabbed an apple from the bowl, and walked into my room.
First impression:
The first time I met Ray was when he came to my hotel room, which was just two doors down from his. God, he was hot. Tall (*praising hands emoji*). Midwestern (or is it Southern?) accent. I like.
My best friend checked in and I responded quickly with a few spelling mistakes, like they do when they first meet the stranger they spent the weekend with, and tried not to draw too much attention to themselves cell phone:
first day:
Thunder doesn’t jaywalk. I noticed this immediately because I am an impatient fast walker. Ray's job is safe so his caution makes sense, but I've asked him to jaywalk with me a few times and he's cool with it. A few minutes into our walk in Portland, he noticed that I wasn't paying much attention to the street lights and would sometimes wander off the sidewalk, so he and I switched places so I wasn't near the street. I quickly nicknamed him "Mr. Safety."
Ray's character is very similar to what I imagined, but there are many things that cannot be seen from a person's words and expressions. We all have opinions about ourselves and how we want to appear to strangers, but that's not always the case when we're face to face. For example, he was a little more serious than I expected - still had a great sense of humor - but I didn't realize through text messages how introspective he was. I remember his bio saying he was calm, but again, that was more of a vibe you would get from him in real life.
Ray is very accommodating. I knew this when we texted and it made me happy to see him, but it was really refreshing to see it in person. A few years ago, when I was single for the first time in a long time, it was the moment in my life when I really learned how to go with the flow. I stopped trying to control things around me, stopped planning things, and started embracing change. I became more outgoing, less reserved, and a little fearless—at least enough to go meet a stranger in Portland on the weekends. I knew we had common interests and improvising would be good for us.
After exploring Portland for a while, we stopped at the local Burnside Brewing Company before heading back to the hotel to watch and chat at Insane Pools . We called it a day and Ray returned to his room. I feel more comfortable with Ray than I did a few weeks ago, when I was drinking with a guy I went to college with and had about 15 mutual friends with.
Talking to Ray was easy, really easy. I quickly forgot our situation.
the next day:
The next day we took a cab to the airport so we could rent a car and explore the Columbia River Gorge Falls. "So what brought you to Portland?" our driver asked. I couldn't say the right thing, so Ray took that line.
We picked up the car, went to McDonald's where I had my first egg waffle, and then hit the road. We stopped at one of the waterfalls and took some photos of the landscape, which looked like something out of The Twilight Zone , which Ray told me he watched with his mom.
We decided to drive to Cannon Beach next. During the two-hour drive to the coast, we sang Sugar Ray, Incubus, and All-American Rejects, and reviewed a new Taylor Swift song that none 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 frustrated I was with pushy guys and how annoying it was to have people you hit it off with become out of character when you don't go home with them. He explained that he really has no expectations for the women he meets on MissTravel. Ray seemed to have little expectations for things in general. He is not a planner. His life is exciting and he is grateful for it. He will be moving in May but doesn't yet know where.
When we arrived at Cannon Beach we stopped at a state park and walked a few trails that we thought might lead to the beach, but that wasn't the case. Instead, we got beautiful views, nice photos, and some serious laughs as I slid along in slow motion and did my splits in the mud. Ray was polite, but he stepped back, smiled, and took a photo as I sank further into the mud. NOTE: Perforated leather loafers are not hiking boots.
Even though it started pouring, we decided to leave the park and head to the beach. I was ready to run away and play in the rain, but Ray seemed hesitant. I said it didn't matter if we didn't go, and he said I should convince him.
I have to remind myself that I'm not hanging out with a confident east coast guy and I hate that this is what I've become accustomed to. I told him we were going out. We bounced along the beach, which reminded him of Rocky and me of Coldplay’s “Yellow” music video. We even ran for a while on the flat beach and I tried to smile even though he couldn't see my face. We took some photos and laughed at how some rocks in the water looked like penises.
My friends arrived and once again I reacted like a drunk.
I texted my dad that my phone was dying but not to worry because everything was fine, and he responded with a crying emoji. We drove back to Portland, got ready, and went to dinner. Seeing a man sitting alone at a table drinking beer, Ray joked that it was him because he liked to do things alone. Our guess is who that person will try to pick up. But then I found the guy’s wedding ring.
Before returning to my hotel room we went to a bar where we laughed at some of the characters there and drank disgusting tequila shots. Once, as we were lying on my bed, he asked me what I was thinking. For fear of making him uncomfortable, I didn't say what I was 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 a few months later I found out the guy was gay.) Ray went out of his way to make sure I felt comfortable, and I didn't want to risk it.
Day three:
We headed to the airport early and had breakfast at an eclectic beach-themed restaurant at 7am. We laughed at our waitress, who looked like she had drank five and a half bottles of Red Bull. The weekend sounds like a lot of time to spend with someone I've never met, but I feel like it's too short now. I didn’t really think about how we would say goodbye or what would happen next.
Ray's flight was earlier than mine, so he finished his meal quickly, hugged me, and said it was nice to see me. I recall the three outcomes he proposed before we met. The next morning, I received a request from him on LinkedIn.
Thoughts afterwards:
Ray was fun, entertaining, and went out of his way to make me feel comfortable. I wasn’t afraid that he would see my clumsiness, or how terrible I was at navigating the passenger seat, or that he would judge me like a New Yorker for ordering a salad.
When you travel with your significant other for the first time, it can make or break your relationship. It usually doesn't happen until several months later, which is often thought to be when people's "true" selves reveal themselves. But when you travel to a new place with someone you don’t know, it’s like an alternate reality—you might let your guard down, have deep conversations, and get your emotions running high, but how real is that? I think you might figure this out in time.
It’s truly worth the 2000+ mile trip for a great weekend. Depending on how you feel about long distance relationships and if you're capable, I do think this might be a viable way to meet someone.
When I came back to New York, everyone asked me if I was in love. Even the guy sitting next to me on the plane who was obsessed with my weekend was curious. Yes, it would be a good story, but no, I'm not in love. I spent a great 41 hours in a new city with someone I just met.
I don't know if we'll ever see each other again. He looks great but I've only known him for less than two days and vice versa. As he points out, we are all busy people. So maybe we'll stay in touch and let nature take its course.
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