I Flew 10,000 Miles For A First Date

Many of us approach first dates with a certain amount of caution. We research our romantic prospects on social media; we plan drinks instead of dinner in case we need to make a quick exit. Then, there are those of us who throw caution to the wind and fly halfway around the world for a first date.

Thanks to the Internet and our newfound ability to video chat, text message, and Google-stalk our way through a brief background check, it’s not too difficult to connect deeply with people we’ve never met or have met only briefly. That’s exactly what happened to the four women and one man whose stories are shared below.

These people flew anywhere from 1,944 miles (Los Angeles to Atlanta) to 10,617 miles (New York to southern Australia) for that first date — all on a hunch that their voyages would be worth it. From the woman who couldn’t stop thinking about a fellow bridesmaid to the New Yorker who was flown cross-country by a matchmaking service, these folks took the ultimate leap.

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I Had Never Seen My Boyfriend IRL…Until I Flew To Australia To Move In
Who: Jill Rosado, 26, NY, designer
Where: Adelaide, South Australia

Last July, I packed up my stuff and left for Australia. It was my first time flying out of the country, and I was going to go move in with my boyfriend of one year. The thing is, I had never seen him in person.

We met on a creative-writing forum in 2009. He messaged me something like, “Hey, I think you’re really cool. We should get to know each other.” I was suffering from anxiety, and I was previously in an unhealthy relationship, so I really needed someone to talk to. He was that person for me.

He became my best friend; I knew everything about him, and he knew everything about me. In 2012, we started talking every day, even with the time difference. At first I was like, there’s no way in hell I’m going to have a relationship with a guy in Australia! But, then things kind of escalated, and we had a serious talk on Skype, like, “Listen, I really like you. We need to give this a try.”

People ask me all the time, “How can you fall for someone when you haven’t seen them in person?” I don’t believe in love at first sight, and I think people can click whether you meet in-person or not. My boyfriend and I spent a whole year and a half relying on Skype. By the third month, we had fallen in love. So, I decided to visit him in Australia after I graduated with my master’s degree. I got a passport, and then a work-and-holiday visa that allowed me to stay for a year.

When I got off that plane, I was a walking disaster — my hair was a mess, I had dark circles, my body was stiff from sitting. But, the first time I saw him, he just smiled at me, and it was wonderful. We hugged for a very long time, very tightly. We kissed — our first kiss — and I just melted. It was like taking a bite of chocolate for the first time. That’s when I knew, yeah, he’s the one. I just didn’t want to stop. Finally, I looked at him and said, “I really love kissing you…but I’m so tired.”

Going from Skype and text messages to physically being there and living together, it was just so much fun. It’s like, Oh my God — you’re for real. You’re this handsome in real life. And, you’re mine. It’s the best feeling. We play video games, binge-watch television shows, and cook dinner. It’s just shown us how well we really connect. We are just made for each other.

I can’t afford to renew my visa, though, so I’m heading back home. I love this country, and my goal is to live here more permanently, but for now it’s back to long-distance. He plans to visit me in December. He’s not looking forward to the winter, but it’s going to be really fun throwing a snowball at him. And, he’s already mentioned that once he graduates and gets a job, there will be a ring on my finger.

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I Spent Thanksgiving With Someone I’d Only Seen Twice
Who: Mimi Shih, 32, New York, investor
Where: London, U.K.

I met Pete through work when I was visiting London. He was very friendly, telling me all these cute jokes. He connected with me on LinkedIn afterwards. I asked for recommendations around London, and we kept emailing. He came to New York for work five months later, so we met up a few times. After he left, he sent me an email saying, “I have to see you again.” So, I decided to go to London.

Honestly, the decision was kind of like a “YOLO” thing. I had never done anything like this before. But, I wanted to see Pete again, I kept thinking about him, and I was just like, I’m going to regret this for the rest of my life if I don’t go. So, instead of seeing my parents for Thanksgiving, I bought a flight to London to see this random guy with whom I’d never spent more than a dinner.

All my friends were like, “Wow, you don’t even know if he’s a serial killer, if he’s a slob. He could literally put you in a dungeon and kill you.” I hadn’t thought about those things; we were emailing five times a day at that point. But, I tried to take precautions: I friended him on Facebook and Google-Mapped his address.

When I arrived at the airport, I had butterflies in my stomach, and he was trying to pretend that it was super casual — he was reading a newspaper when he picked me up. He made me a candlelit dinner, we went on a beautiful walk, and it was all very well-planned and romantic. I was like, this person obviously cares about me and wants to make this the best trip ever. So, at the end, we decided to try a relationship.

It’s been about a year, and we’re still together; we see each other every three to four weeks. He’s committed to moving to New York; he was here for three weeks in February, and we just stayed in and did nothing because it was really cold. I was like, I hope you’re not bored, because this is what our life is going to be like.

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It Was Love At First Sight, But She Was Leaving For Atlanta
Who: Laura, 34, Los Angeles, grad student
Where: Atlanta, GA

We had our first kiss at a bachelorette party — we were both bridesmaids in a wedding, and we were just immediately fascinated with each other. So, we were on the dance floor, and we kissed. We completely lost track of time.

It was a really intense chemistry, which had never happened before for me; I thought love at first sight was a myth. But, when I met her, it was totally different. After the wedding, though, it was just like, “bye.” I lived outside of Los Angeles, and she lived in Atlanta. We didn’t think we would see each other again.

Somehow, she had my phone number, so we started texting constantly, plus phone calls when we could fit it in. I got a $400 bill that first month; I had to switch my plan. Since I had never dated a woman before, this changed my world. I needed to find out what was going on with her, and I needed to see her, so about a month later, I put a flight on my credit card and was like, “I’m coming. Can I stay for the weekend?”

I guess it was a little bit like an extended weekend-booty-call date. I remember when the airplane was landing, I started to hyperventilate because I was super nervous, and this old lady next to me thought I was scared of flying and tried to calm me down. I got off the plane and went to the pick-up location, where there’s a really long escalator, and I remember coming up that escalator, sort of disoriented, and there she was, sitting on a counter, trying to look totally nonchalant.

When we recognized each other, even though we were scared we might not, we hugged a long, long hug. It was amazing, but also kind of uncomfortable. I don’t remember a first conversation, but I do remember getting to the car and just, like, sitting there, not saying anything. We definitely needed a buffer.

But, then, we got back to her apartment, and it suddenly felt comfortable. It was a home, and I met her cat, and I was like, oh she kept a cat alive, so that’s a good sign. She had told me that whenever her last girlfriend came over, her cat would always throw up. So, it was sort of a test. I had to pass the cat test. When her cat didn’t throw up, I was like, alright, I’m in.

We went to an art museum in Atlanta and we held hands, walked through the galleries; it felt very comfortable for me. Being in public — being affectionate — was an epiphany for me. It felt right. I remember leaving and thinking, I can’t let this go. I need her to be part of my life. I have to make it work — however I can do that.

A year later, she moved to L.A.; two years later, we moved in together. We still have that cat.

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The Dating Ring Sent Me To San Francisco To Find Love. It Worked (Kind Of).

Who: Britany, 28, NY, writer
Where: San Francisco, CA

When I first heard that The Dating Ring was flying NYC girls out to S.F. to set them up on dates, I was like, oh, free trip to San Francisco! I was definitely excited, but I had low expectations on the romantic front. I thought it was just going to be a great time.

It was a lot of blind dates and mixers for three nights in a row, which was a little exhausting, so on the last night, a few girls and I just went to a bar. Funnily enough, I met someone there. It was a very traditional, guy-meets-girl-at-a-bar thing, and we ended up chatting all night. The next night, my last night in S.F., we went out and he showed me all his favorite spots.

I think we were both really surprised by how well the night had gone, and how unfortunate it felt to say goodbye so quickly. I remember I said something like, “Well, if you’re ever in NYC, you’ll have to come see me.” And, four weeks later, he did.

It was a lot. We talked on the phone every day before he visited. He stayed with me for half of his three-week stay (his family lives in New Jersey), so we got a crash course on being together. It was really nerve-wracking. Like, sometimes, things can go so beautifully on one night, but if you spend more than 12 hours together, it can be totally different. As soon as he got there, however, it just felt very natural.

We’re still dating, and I moved to Portland, so I’ve seen him a lot more — four times in three months. We just decided we’re going to visit each other regularly and see how it goes. Nothing official. We’re both hoping to really make it work, but it’ll probably mean a move for one of us, which is terrifying, since we’ve never lived in the same city before. Even if it doesn’t work out, he’s definitely someone who will be an important part of my life.

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I Met A Girl On A Bus & Flew 4,000 Miles For Our First Date
Who: Jerry, 24, London-based Californian
Where: Nashville, TN

We met when we were both traveling from Dublin to London; we kept bumping into each other on our way to the bus. I kept thinking, Cute girl! Cute girl! Cute girl! and later she told me she kept noticing me, too. I was able to suss out pretty quickly that she was from America — I could hear the southern accent right away. She told me she was from Kentucky, but she was studying abroad about an hour north of London. Since it was late, I gave her my email and told her to let me know when she got back to her place.

We started emailing every chance we could get, so when she visited London before leaving for Kentucky, I hung out with her and her friends. Over the course of two days, I saw her three times, and I saw her off to the airport. After visiting my family for the holidays, I got a $500 coupon for giving up my spot on a flight. So, I texted her, “What do you think about me coming to visit you sometime soon?”

When I talk about it, it sounds really crazy, and it was in fact a little bit crazy. This was going to be our first official “alone time” together, in what can only be described as a four-day international date, even though we had known each other for four or five months by then. The whole time we were planning, I was like, Yeah, this is going to be awesome. But, once I got on the plane, I was just like, Oh my god. I am a moron. Why did I do this? I’ve only spent a couple hours with this girl in real life!

When she picked me up from the airport, it instantly felt normal again. It was fun. It was very extravagant. We booked a hotel. We had Brazilian barbecue, and that is not a joke; Brazilian barbecue is epic.

Still, though, it was a vacation. If I’m honest, I think that attitude of not knowing what will happen, of playing the odds, it might be why it crashed and burned eight months later. I don’t look back negatively on it, even though it didn’t work out. But, we were ignoring a lot of what made it not work. Even then, we knew it was near-impossible.

But, I would do it again. I’m an idiot; I’m aware. I’m moving back to Los Angeles, and my now-girlfriend is in London, and we’re going to try and make it work. But, I’ve learned a lot from that first long-distance relationship, and I don’t like feeling afraid to do things. Living in fear of someone getting close to me feels like the worst outcome.

By Jessica Chou

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