Dateline: "I explain to him that rappers have an awesome lifestyle, and care about the things that matter most in life…"
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8:40 p.m. – I'm in a cab, going to meet a guy who introduced himself to me last week at my friend's birthday dinner at a trendy Manhattan steakhouse. I can't remember much about him, except that he was wearing a suit with pinstripes a little too wide and thick to be taken seriously.
8:45 – I step out of the cab, onto the sidewalk near the bar. He's chosen one of those speakeasy-type places downtown that doesn't have a sign outside.
8:47 – I wait in line as the bouncer, a short white guy in a fedora, greets a hip-looking couple in front of us. One of them asks him how the acting is going.
8:47:50 – The conversation about the acting is going on a little longer than necessary. I'm wearing a cotton strapless dress from J. Crew and loose pearl necklace, and feeling a little out of place.
8:48 – I walk downstairs, and find my date in wool dress paints, those leather loafers with metal links, and a light pink collared shirt. I quickly realize that we will be the douchebag couple at this bar.
8:49 – We order drinks while waiting for a table. The bartender is an Asian guy with a mohawk, who — I'm told — studied vodka in the foothills of Kiev.
8:52 – My date and I make small talk. I find out he works in Stamford, CT. I ask him if he takes the train from the city or drives. He says he drives because the last time he took the train, it was stopped for an hour in Harlem because "some guy was jacking off in front of some girl's face."
8:53 – I nod silently, not mentioning that this happened to my sister on the very same train two months earlier. I ask if they caught the guy. "I think so," he says.
8:56 – The hostess greets us and leads us over to our table. The place is completely packed, and we have undoubtedly the best table — the corner booth. It crosses my mind that he may have slipped her cash in order secure this spot.
8:57 – I look around. Everyone looks a lot more interesting than we do. We are the one couple in the place not wearing wallet chains or cool hats. I find myself wishing I owned a suede belt or earrings with purple feathers.
8:58 – As soon as we order our drinks, he gets right down to business, asking me what five jobs I would want if I could do anything at all. Good thing I spend all day thinking about this. I rattle off my five, saving my true dream for last.
8:59 – "Why a rapper?" he asks, genuinely confused.
10:02 – I explain to him that rappers have an awesome lifestyle, and care about the things that matter most in life. I cite Rick Ross as an example. I add that rappers have flexible schedules and their work can be done anywhere, i.e., a yacht in the south of France, Miami Beach, etc.
10:03 – He says that makes sense, and that I made a recovery from listing "secretary" as number three.
10:04 – I return the question, but instead of answering, he tells me about his real-life jobs. He says he started out as a concert violinist until he had an epiphany in the early hours of the morning while traveling China. He subsequently quit the violin suddenly and pursued his current line of work as a portfolio manager at a big bank.
10:06 – I question whether he was really a violinist. I find it hard to believe.
10:07 – He lowers the collar of his shirt to reveal a huge scar across his neck from where the violin once sat. I believe him now.
10:09 – He goes back to the subject of his epiphany, and asks me point blank what my religious beliefs are.
10:22 – He tells me his father is homeless.
10:31 – I ask him if he likes his work. He tells me he hates it, but that it will help him achieve his "real goal" of owning a huge fleet of cars.
10:42 – He's turning out to be the most unstable person I've met, on a date or otherwise. But I am weirdly intrigued by him.
11:05 – We head out and grab hamburgers at a nearby fast-food place. As we walk, he asks me if I ever think I'm crushing a small universe when I step on an ant hill.
11:25 – It's getting late, and I need to get home. He hails a cab for me. I step inside and he says goodnight.
11:28 – He sends me a text saying he had a nice time, along with one of those weird smiley faces with a hyphen for a nose. I could see him committing a serious crime under the right circumstances.
11:29 – I will definitely be seeing him for a second date.