When she asks about you, never explain what your actual role is. Keep it simple: Bond trader. Investment banker. Nobody cares if you are a Latin American retail equity portfolio manager. Just say Latin American trader and know five important words in Spanish like beautiful, dinner, wine, penthouse and Cabo San Lucas.
If you work on a trading desk, never say you are an analyst. Don't advertise you are the lowest man on the totem pole. Unless you want her next sentence to be, "Great. Can you go to Starbucks and grab me an venti iced half-caf vanilla frappuccino with two Splendas?"
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When she asks where you work, always say Goldman Sachs. It just sounds better. It's like saying you went to Harvard, your watch is a Rolex or your cocaine is Colombian. If she calls your bluff, say you used to work there but left because of the cut-throat culture. You love the people and the culture better at your new firm, Intellectual Capital. She'll say, "Ooh, that sounds smart!"
Get on the board of a charity — preferably one that involves dogs. It will show that you have a heart. Like Gordon Gekko said, "That's the one thing you have to remember about WASPs: They love animals and hate people." Also, make sure the charity has one good party/fundraiser per year. That way you can invite her to this cool event, with a three-hour open bar and, if you play it right, a nightcap at your place.
On your second date, take her somewhere out of your comfort zone. This will show you are vulnerable. Take her to a place where you are the only Wall Street person there — like a karaoke bar. There is nothing that shows character more than going in front of a group of strangers and singing her a ballad. I suggest, "I Can't Help Falling in Love" by Elvis or for a duet, try"Just Give Me a Reason" by Pink. (You saw "Top Gun," right? That stuff works. "You never close your eyes...")
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Always overtip. There is nothing in the world people hate more than rich people — except cheap rich people! Tip 30 percent. If the meal is $150, who cares about the extra $15? You don't think the bartender is talking crap about you when you are in the bathroom? You want him on your side. If you have the waiter, bathroom attendant and parking valet on your side — you are golden.
Be yourself. Unless you are a total douchebag. Then watch "The Notebook" and try and be more like Ryan Gosling.
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— By Raj Mahal
Raj Mahal (that's his stage name) is a former Bank of America trader-turned-comedian.Catch his next stand-up show at Gotham Comedy Club in NYC on Feb. 25 at 8pm. Follow him on Twitter