The profile intrigues me. The woman has everything I seek – the education, the cultural interests, the open smile with a hint of sauciness (lingering, intimate weekends), a passion for Judaism. I sense a connection. I write, she responds, we meet at a café midway between our suburban homes. Sitting outside on a spring evening, time simply stops as we both wonder if this could mean something. We kiss goodbye and then write to each other later that evening. We’ll meet again. Soon.

OK, that’s the fantasy. Here’s the reality. Same starting point, different direction:

The profile intrigues me. The woman has enough personality so I write to her. She writes back and we agree to meet. Sitting inside a Starbucks® on the Upper West Side of Manhattan on a fall afternoon, I sense little connection. She’s tired from hard Halloween partying the night before and doesn’t want to get a drink. I settle for tea. After 15 minutes she says, “I don’t think this is a love match so I’m leaving.” And leave she does, as I sit there gaping. We’ll never meet again.

Such awkward moments are part of dating. You’re out there emotionally, revealing hopes and fears and your brightest smile. Do it long enough and you get a thick skin that still bleeds easily. Sure, you want to leap into the great romance of your life, but that electricity doesn’t always strike. More often, you’re drenched in a chill drizzle of encounters that range between wryly amusing (in retrospect) to heartbreaking. I detail some of them in my book A Kosher Dating Odyssey: One Former Texas Baptist’s Quest for a Naughty & Nice Jewish Girl.

Weird moments typically happen on a first or second date when you’re sorting out early impressions. Consider my time with a woman I’ll call Spygirl. On the surface, we looked way promising. Like me, she was from Texas and we both worked in corporate communications – in fact, our employers were direct rivals. And that started the problem. We had one date that worked out well enough, then scheduled another, just for a coffee again. This time, Spygirl started asking, rather aggressively, for confidential documents from my company. Her tone struck me as bizarre. Was I her romance interest, or a patsy in a corporate espionage ring? I declined, of course, and Spygirl’s peculiar behavior pushed me to run for the exits.

Speaking of Texas, I once had an IM from an attractive woman involved in the arts in that state. She was a bit younger than me, and her smart ‘n’ sassy profile made my heart go pitty-pat. Alas… it turned out this woman was my second cousin and we’ve known each other since childhood. Our mothers were first cousins so, no dice there. File under “awkward, but funny.”

Then there was Sparkles, a fellow suburbanite. One Sunday evening at her house we were trying, reluctantly, to move the date to its conclusion. With the weekend kid hand-off looming, we struggled to get me out the door. Keep in mind that Sparkles was a curvy armload of a gal and I liked the feel of our farewell hugs. The seconds were ticking away, but we just couldn’t disengage as we stood next to my car.

And then the headlights hit us as her ex pulled into the driveway with the kids. I don’t know how much he saw of us – we quickly broke the clinch – but he certainly noticed my battered 1986 Saab in the narrow driveway. Without a pause he backed up so I could make my getaway. By the way, Sparkles’ ex and I had some professional connections (let’s leave this vague) so opportunities for office awkwardness could have reached astronomical levels. Maybe I should have introduced him to Spygirl so she could pester him for documents.

Fortunately, awkward encounters usually last just a few minutes. You meet an ex-flame entwined around her new guy, the doe-eyed IM charmer becomes a strident anti-American loon on the phone, the woman you meet bears absolutely no resemblance to her profile photos (been there, done all of that.) When these moments happened, I gleaned whatever lessons I could, dusted myself off and moved to the next contestant. Sometimes I seriously ached, but that’s the way the game goes.

However, awkwardness could stretch far beyond a phone call or coffee date. Instead, you have stumbled into a dating version of The Twilight Zone, full of shadows, menace, long pauses and no chance for escape. I’m talking about the most hopeful yet perilous phase of online dating: “The Visit.”

Traveling a few hours to another city for lunch is one thing; flying to another country for a week is quite another. I know from experience; meeting a woman in a country where you can’t even speak the language requires a leap of faith and a zen-like tolerance for potential disconnections. I made that leap into disconnection during a trip to meet a woman I’ll call Guapa. We burned hot in the beginning of our relationship, then cycled through periods of stone-cold silence and warmth. While she wanted me to visit, she also vowed to find me a local “girlfriend.” The longer I knew her, the less I knew her, if that makes sense, but I was intensely curious about Guapa. After a local opportunity tanked, I agreed to a week-long visit to a place I’ll call Pueblo Peligroso – Dangerous Town.

Part of the cathedral in Pueblo Peligroso.

Surprises began at the airport, where Guapa met me with her ex-husband. She lacked a car at the time, so the ex agreed to be our chauffeur. At her place, Guapa laid down some ground rules, such as, I couldn’t take photos of her nor get any photos of us together. She was often distracted; I wondered why she even bothered to have me visit. File this under “awkward and ominous.”

She really did pawn me off on a local friend of hers. And guess what – we connected as the local girlfriend graciously showed me the charming side of Pueblo Peligroso. Among other things, we enjoyed a long lunch at an outdoor café across the street from the main cathedral, which we then toured. In all, a lovely, hand-holding day, with photos. While Guapa was a considerate hostess, we never found a comfortable rhythm and the trip ended our rocky three-year relationship. “Awkward” doesn’t begin to describe the visit. The local girlfriend and I remain in touch, although I have not returned to Pueblo Peligroso.

A festive View of Pueblo Peligroso

I like to think every awkward episode was a learning experience. After Guapa, I never took another long trip to meet a woman, for example. I became much more local in what I would consider. In a few years, I met a nearby woman I began dating steadily. I learned what works for me. Reaching that point required leaps into the unknown and plenty of strained moments. Be the encounter a Starbucks one-off or a risky week in another country, I had to find out for myself.

Van Wallach is a writer in Westport, Connecticut. A native of Mission, Texas, he holds an AB degree in economics from Princeton University. His book, “A Kosher Dating Odyssey: One Former Texas Baptist’s Quest for a Naughty & Nice Jewish Girl,” is published by Coffeetown Press in Seattle. His interests include language study, digital photography and Jewish learning.
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