James Carty, 30, a speechwriter for a mental health nonprofit organization, and Jade Vakilzadeh, 25, an account manager for a health-care consulting firm. (Daniele Seiss/Daniele Seiss)

Whether a man upholds principles of chivalry — or signals that he thinks it's dead — can make or break a potential match. In my short time writing Date Lab, I've now heard multiple accounts of well-meaning gestures of caretaking on the part of men that went over about as well as if they had kept inserting "actually" in a conversation about feminism. But in the case of James Carty, he unknowingly erred too far on the side of under-chivalrous, rather than over-chivalrous.

And it had been going pretty well! Both James and his date, Jade Vakilzadeh, described their three hours at Darlington House in Dupont Circle as "fun." The whole evening buzzed with a sense of mild inebriation. James got there early and immediately ordered a Negroni, and then another after Jade arrived and ordered a mojito. (She'd already had pre-game drinks with her roommate to loosen up.) Then they were informed that some diners whose identities remained a mystery had bought them drinks. So they added wine on top of their cocktails.

"There was one moment where I was like, 'Ooh, I can feel it, so maybe I'll enunciate a little bit better,' " recalled James.

Jade is 25 and describes herself as a "Type A minus" personality, which she translated as: "I know what I want, I know how to get it … but I'm a little laid-back." She works in health-care consulting and says that although she's actively seeking a relationship, she's not desperate, invoking the classic "Clueless" line, "You see how picky I am about my shoes, and those only go on my feet."

James is a speechwriter for a mental health nonprofit group. At 30, he's feeling "a little" self-imposed pressure to settle down. "I spent the summer watching my friends get married, so I'm trying to get back into it," he explained.

Over a prosciutto appetizer and entrees of gnocchi for him and cavatelli with lamb ragu for her, Jade and James talked traveling (he grew up an Army brat), immigration (she's half-Iranian, half-Italian) and pop culture with nary an awkward silence.

"We seemed to be copacetic about most stuff," James said. They're both liberal, although they didn't really talk politics. And they were on the same page when discussing the Hollywood/media sexual assault allegations that seem to surface daily. Also, James did not set off Jade's boor detector. "I'm so glad he wasn't a total creep, because I've definitely been on dates where guys were weird or made me feel uncomfortable," she said later. "He was very nice."

But once you pass "not creepy," there's still a ways to go before you make it to captivating. And although James described Jade as "very cute," Jade said, "he's a cute guy, but definitely not for me." Her type apparently is more "super preppy guy, evolved frat boys."

Still, she hadn't counted James out completely until their check came and it ran $70 over the amount The Washington Post had agreed to cover. Jade said James suggested that they split it, which cooled her on him even further. "As much as women's equality is a thing now, and whatever, I do think that chivalry is not dead and should not be," Jade said. "When a guy offers to pay ... it shows a sign of, 'I'm interested in you and I want to keep this going.' "

For his part, James wasn't trying to make a statement when he suggested going Dutch. "In this case, I really didn't give it a thought," he said. "In the age of Venmo, etc., splitting the check has kinda become a matter of course."

When I asked him about his thoughts on chivalry later, he said, "I don't have a rebuke for chivalry, but I think the concept is a little paternalistic and outdated."

As Jade waited for her Uber, he unwittingly disappointed her again, by not being the one to suggest that they hang out a second time. Jade said she did, even though she wasn't really invested in doing so. Then he asked if she wanted his number. But that struck her as "a little passive," she explained. James said, in the end, their interaction "didn't scratch the surface too deeply." But clearly Jade had seen enough.

Rate the date

James: 5 [out of 5]. I had no expectations. We ended up closing the place down.

Jade: 3.75. He was nice to hang out with, but if I never saw him again I'd be okay.


"I texted Jade the next day and she never responded. Oh well," James said.