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Dating in New York is risky business if you ain’t got a swagger like moi, and it’s even worse if your name’s not Lil Wayne. Money still has its place in amore and, unfortunately, a lot of y’all ladies got Gucci bags for hearts. I’m not the wealthiest guy on Earth – hell, I get paid to play video games, talk to celebrities and watch movies – so stuntin’ ain’t a habit for yours truly. In the end, though, a gentleman shows a lady a nice time, but even going dutch on a date has its hassles.

The good folks at Tribeca Grill were kind enough to let my date and I dine and, after a hearty meal of steak and potatoes, we went in on the wine selection. Her almond skin was glistening, with deep, suggestive eyes, captivating anyone who wished to stare in her direction. With a buttery smooth voice, she asked, “How come men don’t show out anymore?

Me, being the liberal-minded man, joked, “Because… women don’t put out anymore.” We laughed. Her eyes squinted, feigning anger. See, this girl didn’t have the problems of being too young at an old age, and she wasn’t a nympho, either. She was like Lauren London on a budget. More wine was consumed and her mind sex game was poppin’! Over a rousing game of “Innuendo,” she managed to compare Lewinsky to boxing (“headshots”, she says…), explained why McCain’s a pimp and hilariously spun a story about what Superhead’s retirement party would be like – without the anal beads! (NSFW)

I had to admit, though, shawty was a catch and I wanted to make sure that I did my duty to keep a smile on that pretty girl’s face. When our waiter returned with the bill, he placed it right in front of me, my face confident that my InteractiveOne check was in the account.

Now, before I go on, I have to say that asking for anything must be a tough thing for anyone to do and even worse when you’re asking it from a sista who clocks six figures and “don’t need nothin’ from no man!” But I figured that, being in the 21st Century, we would find black love on the upswing and feel that we’ve defied simple stereotyping and gender labeling.

Hey, baby, you think you can leave the tip?” I ask. Let me tell you… that pretty girl’s face turned Khia really quick! “You asked me out and can’t even leave the tip?” (That ball-stomp cost me 78.41 USD pre-tip, and I tried to hold back from going all New York-ish…) I felt a lil’ steam off homegirl’s neck, and wanted to now see if she just needed to vent.

That’s what’s up,” I say. Suddenly, I felt the ghost of Eddie Murphy creep into my soul, and God does work in mysterious ways! Truly! That sexy mug of hers just got more and more sad-faced, but I didn’t understand why. Trying to be Mr. Sensitive, I say, “Look, let’s just try to be fair, I’ll throw half in, on top of whatever you put in, okay, darlin’…?” She regrettably smiles, opens up her Gucci bag and pulls out this big Ziploc bag of change.

— Insert awkward silence here —

She smiled to break the ice, but somewhere, someone was laughing at this predicament. As homegirl kicked her rap about how she’s “frugal,” I noticed how her game was so on point that she managed to just leave a dollar tip, which pissed off our waitress, for sure! I put my dollar next to hers, flashed a warm smile (while my mind was searching for the next thing to say) and we exited the Tribeca Grill with smiles and giggles still in tact.

Ladies… was I wrong somewhere? Would it have been better to go the whole nine yards ’cause it’s a date? Or does common courtesy have its say? Speak on it!

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