Making Sense of the Trip I Never Took

Would you allow a wealthy stranger to fly you away for your first date? I almost did.
Publish date:
June 6, 2012
travel, Dating, mexico, the Daily Mail, Miss Travel

Emily sent me a link to this article that ran in The Daily Mail, "Would You Allow A Wealthy Stranger to Fly Your Away for a First Date" because well, I almost did. Sort of.

While author Joanne Hegarty uncovers the inner-workings of a relatively new online match-making service called Miss Travel, that offers “attractive” women free access to paying suitors looking for someone to spend their air miles on, my experience didn’t begin online.

Here’s what happened: I met K at a sports bar after one of his girl friends introduced me. First she bought me a shot because I'd been dropped by the couple I was third-wheeling on that night and I needed it. K was tall and friendly and we talked easily. And the fact that a cool girl co-signed on him also was a huge plus. We exchanged numbers and he texted me the same night to make plans.

Unlike the other dudes I have met in my new life of singledom, K was really funny. The only drawback? When he wasn’t being hilarious, K switched to showing off about something expensive. From his two cars to a recent jaunt in Milan, K wanted to make it clear that he had money.

When it comes to income, I like a dude who keeps it discreet, but I didn’t let it get to me. Just have fun I thought, just give it a try.

The second time that I went out with K, we had dinner followed by a night of wandering from bar to bar – standard protocol on a good date. At one point we stopped at a kitschy Tiki spot in Alphabet City where the cocktail menu looks like that of a cheap resort. I'm totally into this kind of thing and it sort of negated the bragging from before.

A few drinks in, we noticed that the couple accross the bar was dressed in military gear from the 1940s and made a bet on whether they were in costume or just really loved Pearl Harbor. The loser had to take the winner to Mexico. You know, because that’s extreme and no one would ever follow through on such a promise, right?

In Hegarty’s investigation of Miss Travel, she comes to find that most of the so-called jet-set daters using the site talk a big game, but rarely follow through.

This is ‘Nomad’ a ‘well-groomed, well-travelled’ marketing director from Central London who claims his annual income is up to £800,000. Not surprisingly, he says he likes ‘the finer things in life’ and his favourite drink is Krug champagne. Sadly he’s single because ‘these days Terminal 3 at Heathrow seems to be my second home and my suitcase my best friend’.

But, just like the last Englishman, Nomad seems to have a problem opening his wallet. The best offer he comes up with is ‘a drink’ in London before he jets off again.

Well, K lost our bet, but he upheld his end of the agreement. He texted me after we had both gone home and asked if I was serious about going to Mexico. "I'm down!" I said, still drunk and certain it wouldn't actually happen. The next day he called me asking for my passport number so that he could book flights.

"You're stealing my identity aren't you," I said, half-joking.

He laughed it off and gave me an easy out in case I had changed my mind. He wanted to go for a week, a lengthy stretch of time to spend with one person, even someone you love. K on the other hand, was practically a stranger. Still, the trip wouldn't be for another two months and if we were still dating by then, I would want to go, I reassured myself.

In the weeks that followed, we continued to date sporadically. He traveled often for work and we were both busy. Despite enjoying his company, I couldn't shake my anxiety about going away together for more than a weekend. We weren't even sleeping together. I played out lengthy scenerios with friends about being murdered or sold as a drug mule. When I asked you guys to weigh in, I was met with an almost unanimous "Go!"

The night before we were set to leave, K and I had dinner and discussed the upcoming trip. Conversation didn't come as easily as it once had, and something felt different. Maybe we were just nervous.

In the morning, I got a call from my father. My grandmother had been admitted to the hospital and she wasn't going to pull through. Within a few days, she was gone. I skipped Mexico and joined my family, while K went alone. To think of my grandmother's death as "fate" seems self-serving and awful, but I can't help but wonder if the timing was more than a coincidence.

I still don't really know what to make of what happened.