I thought Ricky Barrios, 32, a technical writer and self-described “jokester” who dabbles in stand-up, might be up to the task. The Chicago native says he has dated a bunch but hasn’t had much luck with long-term relationships. “It used to bug me a lot, like, ‘Why don’t these people like me?’ But I’m just going to live my life.” He wants someone who “has it together” because, he explains, “I have a lot on my plate and I’d like to be with someone who would make it look like less.”

We sent the pair to Penn Quarter’s Cure Bar & Bistro, which takes a farm-to-table approach on cured cuisine. There were some rocky moments right off the bat. Ricky got there first and took a seat in a secluded booth. When Isabela arrived, Ricky confessed, “I had an awkward time trying to get out of the low, squishy booth. I scuttled out to give her a hug, but she had extended her hand — that wasn’t a great start.”

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But Ricky had come prepared with a funny opener: He handed Isabela an article on how to escape a bad date. Unfortunately, Isabela said later that she found the gesture more strange than funny. She recalled thinking, “He meant it as giving me an exit strategy, but also saying, ‘I’m prepared, I have an exit strategy.’ Maybe he was not very optimistic.”

Ricky saw that his joke had fallen flat: “She skimmed it real quick and said, ‘Oh, I already know these.’ And she didn’t even crack a smile.”

All was not lost, however. When Isabela ordered the wrong drink, she found it “very sweet” that Ricky rushed to get the waitress to change it. He scored another point when he suggested ordering a bunch of appetizers to share. “I like that he was into food and was curious and open to try things,” she said.

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As they sipped drinks — red wine for her and an Old-Fashioned for him — and munched on octopus and mac and cheese, they got to chatting, and the evening seemed to be on the upswing. “We had a lot of cool things to say to each other,” Ricky recalled. And talking to her felt “very familiar.”

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“At no point did I feel like escaping,” Isabela said.

Ricky found Isabela’s work as a mediator fascinating: “It is cool to speak to someone who has expertise in a field that I don’t.”

“We talked about a lot of different things. There was a mutual exchange,” Isabela told me. “He would make a fantastic lawyer. He’s a good listener, but an even more avid questioner.”

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As they moved on to another round of drinks, the conversation turned to dating, and that’s when Isabela said their differences became clear. “He’s never had a serious relationship,” she said later. She treated the information with “neutral curiosity and understanding [but] I didn’t feel like I was getting the same [from him].”

Ricky, she recalled, “was surprised at how friendly I am with [my exes].” When she told him that she had given a couple of them a heads-up that she’d be on Date Lab, “I think he was reading into it and thought I had a messy involvement with them,” she said. And Ricky wouldn’t let the matter drop. “I was flustered that I kept getting questioned about that topic,” she told me. He seemed “judgmental” about it.

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Ricky said later, “I just think if it’s your ex, you shouldn’t be keeping tabs on each other’s romantic happenings.”

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On the positive side, Isabela, who was born in Brazil and grew up in Miami, said she did feel a connection with Ricky, who is of Salvadoran and Guatemalan descent, through their experiences of growing up speaking Spanish and their closeness with friends and family. Ricky in particular was moved by how close Isabela is with her autistic brother: “When she talked about [him] there was a level of empathy and level of care she takes with her family,” he said.

That sense of connection was enough to keep them going for another round of drinks and dessert. They hugged goodbye around 11:30. But by the time we spoke the next day, Isabela wasn’t sure why she stayed so long. “I would have been done in two hours instead of four,” she said. For Ricky, any romantic prospects had evaporated by then, too. He said he had “a sense of deja vu” during the date. “Then it hits me!” he said. “ ‘She reminds me of my cousin!’ I love my cousin, but I would not date my cousin.”

Rate the date

Isabela: 3 [out of 5]. “We weren’t a match, but it was better than most first dates.”

Ricky: 3.5. “The romance wasn’t there, but I wasn’t bored for a second.”

Update