Before moving to Washington, Ari Jacobson made a living singing on cruise ships. He released an album (fans, his website notes, have described him as the "male Ani DiFranco"). Four years ago, while visiting a childhood friend and his wife here, he decided to audition for some plays. He was cast in a theatrical production of Franz Kafka's "The Metamorphosis," grew to love the capital and its vibrant theater scene, and decided to stay.

Ari, now 35, still acts in plays and performs regularly at bars and restaurants — he has about 500 to 600 covers he can perform, a holdover from his time on cruise ships. During the day, he works at preschools and child-care centers, doing baby and toddler music classes, performing “various forms of kids’ music, Jewish music and Jewish kids’ music,” he says. The gigs keep him busy: An hour before his date, Ari was singing at a toddler’s birthday party.

He put down the musical shakers and bid farewell to the kiddos to meet Vicky Markovitz, a 33-year-old editor for a higher-ed association, for a Labor Day date. Vicky is a poet and a big supporter of the arts — she goes to shows every week to see her favorite local bands (she gave special shout-outs to Ex Hex, Erotic Thrillers, Des Demonas and Yes Vacancy). She volunteers with Split This Rock, an organization of poet-activists in the District. Her brother is a musician, so she understands the hustle of being an artist better than most.

Vicky had sent in her Date Lab application because “I want to show that I’ve tried it all,” she says. She’s been on all of the dating apps. She’s tried meetups. She’s even done speed dating. “I can’t recommend that,” she says, laughing. Putting herself out there for dates that don’t end up working can be discouraging, but she tries to stay open to new experiences. Meanwhile, Ari applied because some of his close friends are loyal readers of this column and even read them aloud using different voices for the daters. “My biggest fear was: Don’t do something that will make [them] read me in a funny voice,” Ari says.

Ari and Vicky met at Ankara in Dupont Circle and shared the bottomless mezze. They compared notes on their travels. They talked about the theater productions Ari has been involved in and the plays Vicky has seen. He was fascinated to hear that she had worked on an archaeological dig in Peru in grad school. They discussed the challenges of having a career in music. They both really enjoyed the colossal grilled shrimp.

But while they had plenty to talk about, there was one major difference between them. It had to do with their approaches to dating. “It can be a little hard to feel chemistry right away,” Vicky says. “What I usually use for my judgment is if I had a good time and I enjoyed the conversation, to see if someone is interested in a second date, and not even focus on long-term anything — just stay in the moment.”

When I asked what he was looking for, Ari said that he couldn’t describe exactly what it was — and then proceeded to give a very detailed description of what he was looking for. It’s that ineffable combination of mutual attraction, reciprocity and compatibility. “You know within the first 30 seconds of meeting someone whether they’re a candidate or whether there’s potential,” he says.

Unfortunately, Ari says he realized within the first 30 seconds that the sparks weren’t going to fly between them. So at the end of the night, when she asked if he wanted her number, he told her the truth: He didn’t see a romantic connection developing. “If there’s one thing I’ve learned it’s to be super upfront about that,” he says. The lesson he has taken from being on the other side of rejection is that “ ‘no’ is so much kinder than ‘maybe,’ for both sides.”

Vicky took it well. “He said that actually he didn’t feel a romantic vibe, but I’m really glad he was honest,” she says. She wasn’t necessarily feeling it either, but she was still open to getting to know him further. Still, she’d rather take the truth than a brushoff: “I 100 percent supported the honesty.” And though the date ended anticlimactically — they hugged and no numbers were exchanged — she counted it as a success. “My things were just hoping I’d meet someone, get along and enjoy some free food together,” she says. “That definitely happened.”

Rate the date

Vicky: 4 [out of 5]. “That special something was missing, but that you can’t really control.”

Ari: 3. “Definitely on the positive side, but for a 4 or 5 you’re hoping it will lead to some future romance.”

Update

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Marin Cogan is a writer, senior producer, and co-host for Pop-Up Magazine.