Drew Calcagno is a 26-year-old naval officer who is looking for “a girl who really loves dressing up and going out often” and “can introduce me to creative corners of the city.” Rebecca Renton is a 21-year-old fashion forecaster and photographer. She’s seeking someone who is: “Smart! Clean-cut with a bit of a creative streak. Confident and charismatic, a bit of a chatterbox.” (Daniele Seiss/For The Washington Post)
Boston native Drew Calcagno, 26, is a military officer and a Fulbright and Rotary scholar. He also "adores cocktail bars" and is an aspiring menswear designer. "I'm into streetwear and I've been sketching. If you match me up with someone who can sew, that would be great," he told me.
I wasn’t sure if she could sew, but fashion forecaster and photographer Rebecca Renton, 21, seemed like a perfect match. The part-time Virginia Commonwealth University student has been working in the Washington area professionally as a fashion concept designer and artist while completing her degree. “I’m in school, and I have a hard time meeting people outside my circle, which is very female- and queer-dominated — and I am very straight,” she explained. She prefers dating older men because “I’m ambitious and it’s rare to find it in a 21-year-old guy.”
We sent the duo to K Street’s American Son, which features an Asian-inspired take on American cuisine and is inside the trendy Eaton DC hotel. It turns out the Eaton is one of Drew’s favorite haunts: “I know everyone who works there.”
When Drew first laid eyes on Rebecca, he was “instantly into her sense of style and knew that’s why we were matched up.” Her “cool white jumpsuit” showed “she was confident.”
Rebecca said he was “cute” and “looked nice,” but his streetwear choice gave her pause. “The shirt was very Forever 21.”
Over drinks (a carrot-ginger cocktail for her and a cherry-blossom-inspired sake drink for him), they “hit it off right away,” Rebecca said, discovering a shared passion for fashion, art, design, as well as education. She was in the midst of applying for a Fulbright to work on a film on street fashion, and he gave his insight on the program. Drew said, “It was exciting to hear about her process of designing clothes.”
As appetizers of potato croquettes and ceviche arrived, they dished on the D.C. art scene. Rebecca described it as “institutional” and “sterile,” compared to the more “punk, artist-led, DIY spaces” she prefers in Philly and Richmond.
Drew said later that he was a tad miffed by her comment. “It’s in vogue to say the art scene in D.C. is super boring, corporate, political, and there’s no creativity,” he said. “It’s my mission to find reasons to not buy into that. I think there’s value in finding the little niche in the place where you’re at.”
Rebecca recalled that Drew then “quizzed me on galleries, showing them to me on Instagram.” She felt like she was “getting grilled trying to prove” that she’s a working artist. “It came across as ‘Oh, you haven’t been there? I can’t believe that.’ It didn’t feel like a suggestion.”
While they chowed on mains of beef cheek and scallop, conversation turned to D.C. nightlife — something Drew lives for. “If I could, I would go out eight days a week,” he gushed to me. He was excited when Rebecca told him she loved to dress up and go out. “But then she said, ‘I feel like I’m becoming an old lady and don’t go out as much.’ That’s pretty antithetical to my social existence at the moment.”
Though the evening had its ups and downs, both Rebecca and Drew made it clear to me that they admired each other but were not a romantic match. At 9:30, the evening was ending on a pleasant note as they left the restaurant, walking through the hotel lobby and out to the street to make their way home.
But then, Rebecca told me, “something happened ... that really threw me off. Drew said: ‘I had a really nice time. You’re so awesome to talk to and so accomplished.’ And I said: ‘Thank you. I had a great time talking to you, too.’ Then he said: ‘I got more of a friend vibe. Is that okay with you?’ I said: ‘Oh, totally. I feel the same way. I think you’re cool — but definitely friends.’ Then he said, ‘Okay. Bye.’ And just walks back inside — I’m assuming to go hang out with his friends.” Rebecca waited alone for 10 to 15 minutes for her ride. “I was literally getting ditched at the curb,” she said.
Drew admitted to me that he handled things poorly. “Rather than standing next to each other awkwardly, I went into the lobby to order my Uber.” He spied her “still standing and waiting outside” and feared his ride “was coming so quickly, so I canceled it and waited some more. I didn’t know how to say goodbye again.”
His flight response had definitely been triggered. “I instantly regretted it. Obviously, it was a stupid move. I said let’s be friends, then I ran away.”
Rebecca: 2.75 [out of 5]. “That was a major faux pas at the end.”
Drew: 3. “I guess that was probably a bad decision. I wish I had asked for her Instagram. I guess I’m just awkward.”
No further contact.
He gave her tips on how to escape a bad date
Could RuPaul bring these daters together?
Last time, we matched him with an introvert. This time, we tried an extrovert.
