I once dated a man who paid for Pinkberry with his black American Express card.

True Story.

He looked great on paper. He went to an Ivy League college; was the “one who made it” from his family; played tennis every Saturday morning with fellas from his office; and worked in marketing for a MAJOR company. In fact, you probably bought something from his company today.

Don’t get me wrong, he had his quirks–he told me he only kissed five people in his lifetime and he was in love with every one of them. He was also pretentious as hell, and it showed.

I remember our date vividly. We went to a movie, and then drove to Pinkberry. He had been talking about his job the ENTIRE night. How happy he was that he made it. How he was the company’s top candidate (he had been working there five years). How he tries to tell every intelligent Black person that with hard work they, too, can dream of a better America.

Right when I was about to doze off, he pulled out a black Amex to pay for $6.45 worth of fro-yo. I remember the price because I can still see the look the cashier gave him, and me for being with him, when he handed over his card.

In that moment I thought, “Sir, you didn’t have cash for that, or another card, you had to pull out that card?”

Of course, dude pulled out the black Amex right as he was emphasizing how Black folks could make it, if they tried.

I didn’t see him again after that date; his pretentiousness and up-by-the-bootstraps philosophy was just too overwhelming to stomach, no matter how good the fro-yo was.

Have you ever dated someone who was clearly trying too hard?

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