Aggie keeps to himself during the flight. Mark, the tall undertaker, is hidden in business class. Meanwhile, Boston Joe is finishing his ham and cheese. Wiry-haired and furrowed-browed, he looks more exhausted than the others. He rests his head on the seat in front of him as we drift across the clear Caribbean Sea.

• • •

I didn't see Jack again: I later learned that he and Patricia had ordered room service, stayed up all night, then checked out at 4 a.m. so he could catch an early flight. In the weeks after the tour, they took their relationship to Facebook. She communicated through discreet messages, posting a series of pictures of herself—around her house, in her bedroom—and tagging Jack in them: a sweet, clunky sort of "Wish you were here" for the social-media age.

Many men make instant connections with Colombian ladies, affectionately known as paisas. Relationships get messy if the women have children and ex-husbands.

A few months later, I call Jack. His voice is surer than I remember. Since we parted, he's gone on another AmoLatina tour, this time in Costa Rica. He met Mariana, a perky 21-year-old with chestnut eyes, but decided she was too young to commit to. Patricia still wants Jack to come back to Medellín. He tells me that he's not sure.

"I'm definitely attracting younger women. It's a wonderful affirmation," he says. "I'm grateful to the tour—it's kind of like a playground for a straight guy. Having a broken heart was hard, but I'm more confident than ever."

Dave, the dating coach, fills me in on Aggie's journey: "He was asleep during our cultural orientation. The parties in the room . . . He converted his suite into a discotheque! He said that he wants to come back, and that he wants to do it the way the other guys are doing it. He realized that he wants to do better."

The last time I'd spoken to Boston Joe about his luck on tour, he told me that a woman he met at the social had stood him up at the 11th hour. After organizing the date and booking a translator, he ended up with only an e-mail address. "Come on," Joe grunted. "What is that?" Unlike many of the guys on tour, Joe knew without question what he wanted. He told me over and over: "I'm not here to get fucked. I want a partner. I want to meet someone. I want another child."

For most of these men, the search continues. For some, it has already stretched decades long—with no mile markers and no guarantees. Can love be found in a 21-year-old in a kitschy South American club? That's a gamble men will continue to take. These tours, romantic or not, bring hope: that a 2 a.m. Google search, a sip of aguardiente, a whisper in the ear of a Colombian translator might inch him closer to Her.

• • •

Adam Baidawi (@ads_b) has written for the international editions of GQ, Esquire, and Rolling Stone.

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