The Internet-Enabled Dirty Weekend (or How to Do Long-Distance Online Dating Right)

The web is thick with women ready to try something new in a new city.

The first time I did it, I was 29 years old. I’d just had my best year professionally and I was starting to feel comfortable in my own skin. For the first time, I had disposable income, which I used to buy a new suit and a half-dozen shirts, but my sartorial interlude was brief. My foodie period was also abbreviated. What endured was my desire to order in.

It was mid-2006, and Amy-Jo and I were MySpace friends. These were more innocent days, before Tinder and Grindr. Neither of us can remember who reached out to whom, but I do remember that the Kansas native struck me as occupying that sweet spot between terribly cute and extremely sexy.

Soon we were chatting, and given the slim chance of us actually meeting, neither of us were shy in revealing that we were incorrigible perverts. A few sessions of one-handed typing later, I checked my bank balance and asked her if I could fly her to New York for a few nights. She said yes right away, but when I contacted her a few days ago before writing this, she said that up until she laid her eyes on me at Newark Airport, she was fairly convinced that her friends were playing a prank on her. Before her arrival, Amy-Jo and I spoke on the phone just once. That short call took place after I’d purchased her airfare.

We made out before either of us said a word. We almost got thrown out of a cab when the driver turned around and glimped what was happening on the interstate. And after being in my apartment for less then 20 minutes, we’d committed at least two sexual acts that, until 2003, were illegal in the Sunflower State. Amy-Jo wasn’t in Kansas anymore.

When she limped out of my apartment three days later, I was exhausted, happy, and quite incredulous at how easy the whole thing had been. In the eight years since, I’ve flown four or five more strangers into town and I’m happy to report that each and every time, it’s been a resounding success.

But here’s the thing: I live in downtown Manhattan, and you can’t walk three steps without bumping into a smart, interesting, creative, beautiful, approachable, stylish, sexually adventurous woman. So how can I explain why, in spite of this horn-of-plenty, I play the high-stakes game of spiriting unknown women in to stay with me at my tiny apartment for upward of 72 hours?

Because I can.

I’m fortunate to be in a position in which I can throw a cool grand at the prospect of a dirty weekend knowing full well that the adventure could end in tatters. For the better part of my twenties, I could barely keep myself fed, housed, clothed, and shod—and as a consequence, extending the offer of passage to New York still seems deliciously decadent and thrilling. It apparently feels that way for the women I invite as well.

Usually, I have a few years on the woman coming to stay. There’s a certain amount of disbelief on their part that the hours of flirting and sexting with a guy who lives in another time zone actually led to something. They’re excited. I’m excited. Everyone is excited.

Ponying up for a coach ticket on Southwest Airlines isn’t exactly like picking her up for dinner in a Bentley, but I know that the confirmation email in her inbox marks me as a man of a my word, a man of action, and perhaps a somebody worth getting to know.

Because it’s transgressive. 

To me, there’s something very exciting about you and the pixilated figure on the other end of a choppy Skype call agreeing to fuck each other sight unseen. From the moment I buy the ticket, I’m counting down the days until she presents herself at my door. I wile away hours thinking about how our first session will play out. 

I delight in anticipation and the buildup; getting texts from her letting me know that she’s made a waxing appointment a day or two before a nonplussed friend drives her to the airport.

Because the acceptance of my offer tells me so much about my visitor.  

A disposable income is, as the name suggests, disposable. I’m under no illusion that just because I’m the one making a material investment in the weekend, that I’m assuming the lion’s share of the risk. The women are always going to be the one with the most on the line. 

The few friends that she’s told about this sudden trip across the country will likely have told her that the escapade she’s signed up for is fraught with danger. Others may have flat out told her that she’s reckless, irresponsible, even crazy. But in spite of their concerns, she’s still coming to see me. 

To my mind that tells me that’s she’s brave, adventurous, confident, unconventional, uninhibited, and open-minded. These attributes are exactly what you want in someone who’s going to be on your arm and in your bed for a few fun-filled days. These are—more broadly speaking—admirable qualities.

Because the sex is always fantastic. 

A single Internet-enabled dirty weekend can become something else—everything can become something else—but the first time out, neither party really knows if it’s ever going to happen again. 

Over the course of the correspondence, both of us have mentioned what we want to do to each other, what we’re into. With the clock counting down the hours until she’s headed back home, in situ communication about likes and dislikes tends to be forthcoming and clear. The sex can be completely uninhibited. No one is shy about appearing slutty, dirty, freaky, or nymphomaniacal if they’re a red-eye away from disappearing forever. 

Because it’s a gamble. 

Messages, texts, and phone calls can provide a good sense of whether we’ll gel once she’s crossed the threshold, but there’s always a chance that our personalities will clash, that we might not like how the other smells or tastes, that we’ll have no sexually chemistry, or that we simply could find each other loathsome to be around. In the event that this ever happens, it would be incumbent upon both of us to figure out how to make the most of the situation while chalking the whole thing up as a learning experience. 

I’ve never gambled with money but during these weekends I’ve put my time, my sexual health, my home, and my sanity on black and rolled the dice. Luckily, I’ve never once come up snake eyes but the threat of an excruciating mismatch makes congenial company that much sweeter. 

Because it’s contained. 

Though we’re at close quarters, a three-day fling is just short enough for me to be an unflappable, undistracted host, my best self. 

Case in point: When one buxom blonde Texan visitor had her flight cancelled and ended up spending an extra night with me, I found myself struggling to get through those last 12 or so hours. Literally and figuratively drained on all fronts, I white-knuckled it by sheer force of will.

But the surprise extension highlighted a vital ingredient that can make the dirty weekend so fun: brevity. When you’re giving it your all it has to be a sprint, not a marathon. By the time I put her in the cab, I felt like Dallas has done me. I took a knee, iced my balls and gave myself two full days of alone time, but tellingly, we were planning a repeat visit within days.

Because it’s easier than you think.

The more recent cross-continental weekend flings have been facilitated by online dating site OKCupid. My profile does a pretty good job of explaining what I’m all about, and luckily, there’s a whole subset of women who respond to it.

Many of those women are just a walk or a subway ride away from me, but occasionally I get matched with an absolute dream girl who might live in L.A. or Vancouver. If an initial flirt goes exceptionally well and my bank balance is looking healthy, I’m liable to ask them if they’ve ever been to NYC or if they’d like to. Then the countdown begins.

Photos by Natalie Pelosi / Getty Images