Cummings scans the crowd at a swank spot on U Street. An unapologetic bachelor is never not "on," he says. His mission is singular: to find a woman who will accompany him home for one night - and who, if she is just right, will leave with the light of day.
Cummings, 29, wearing a black pin-striped shirt, is in full bachelor mode. Women confuse him with the singer Drake, and he takes that as a compliment. The crowd is thick at Ben's Next Door, where the city's young, black and hip squeeze against the bar or reign from tables in the balcony. It's cold outside, but Cummings pronounces the scene inside hot. Women outnumber men, some of whom hang near the wall, seemingly nervous about approaching a woman. Then there are men like Cummings, a real-life "Hitch," a bachelor who has elevated his craft.
His assessment of the room is interrupted briefly by a woman near the front door. She tells him she reads his blog. She smiles, then tells him that she tried calling him, but he never called her back. It brings the conversation to a halt.
"For a minute, I was like, hell, no," Cummings says later. He and the woman had just met, and already there was potential for drama. This may be one of the reasons he prefers the life of a bachelor - no commitments, no apologies. It's the life he writes about in his blog, Until I Get Married: Inside the Mind of the New Bachelor.
From Howard to NYC
Cummings, a D.C.-born writer and Howard University grad now living in New York, launched his blog a year ago and already has 65,000 followers and the attention of national women's magazines. Glamour.com called the blog "hilarious." He writes about questions such as whether it's better to go to her place or his (hers - you can leave when you are ready). He advises men not to date a woman whose friends are cuter - too tempting. And he lists the types of women men should never fall for, including those who hate their jobs (she's probably whining to a man who hates his job more but isn't complaining) and recent college grads (because you're first lured by her great, idealistic attitude, and then she gets jaded and reality sets in).
He dives into sensitive terrain that a "man's man" might avoid. Like the post he wrote about bumping into his ex-girlfriend on the streets of New York. She was the one he really loved. (He admits.) But he cheated on her. (He admits.) And she left him. (He admits.) And now he is standing in front of her and her swelling belly, pregnant by another man, and Cummings's emotions are swelling, too.
"You came out of nowhere, on 7th Ave, walking in all black everything and your hair worn up like a crown. . . . It was nothing like I expected it to be. I mean, you really are pregnant. . . . You're pregnant with another man's child and not mine, which is weird when you think about how we used to have conversations about what we were going to name our child."
Cummings, who is part African American, part Puerto Rican and part Japanese, isn't afraid to show his emotions. Bachelorhood, he says, is complicated. He writes about the male conversation, the things he and "his boys" discuss when together. He admits that the ticking biological clock bothers them as much as it may bother women: "A lot of it is fronting like we're relieved to not have the stress of raising a family, when deep down inside, we know some of this young man's life is getting old."
'What we talk about'
Bachelorhood is not all fun and games, he says. But he is not ready to let it go.
He pauses. He swivels. A pretty young woman has just entered the room. Cummings nods to his friend, Jermaine Roseman, 29, and congratulates him for choosing the right spot.
Cummings advises women to look for a man who is ready to get married. "If you want to find some dude who wants to marry you, start in your own back yard. Don't start with someone like me."
"The question is, why would you want to marry someone who isn't ready?" asks his friend Cliff Flowers, a 28-year-old engineer.
Women, they say, must study men. Understand their conversations. Wait. And by all means, never settle. And by the way, they advise, take all those photos of you in the "freakum dress" off your Facebook page.
A what dress?
"A freakum dress," Flowers says. "Have you seen Beyonce in those commercials? That's a freakum dress. They come with a tag that says, 'No imagination required.' "
"This is who we are," Cummings says. "This is what we talk about."
The night is still early. When they leave here, they are heading to a bar-lounge. They pass each other copies of keys, in case the person with the original keys ends up going home with a woman.
These bachelors may have arrived together. But the plan is not to go home together.