Gucci loafers

I set up two of my friends on a blind date. My guy friend is a Wall Street type, my girl friend is an artist. He wined and dined her and sent her home in his car with the driver. Thanks to my matchmaking skills, they both had a good time and liked each other. My guy friend called to ask me if my girl friend liked him. I assured him that she did. He kept pressing for details. What did she say about me? Did she say anything? I told him what I could remember, which was all good. Then I remembered.

ME: Well, there was this one thing.

HIM: What? Tell me!

ME: It was about your shoes. She didn't really dig the shoes. She said they looked like Old Man Shoes.

Silence.

ME: You there?

HIM: Old Man Shoes?! She said that?

ME: Yup.

HIM: Those are GUCCI LOAFERS! Those are five hundred-dollar shoes! They're a classic! Everyone wears those!

ME: No they don't.

HIM: They're de rigueur in the hedge fund world! They're practically part of the uniform.

ME: Um, maybe next time you should wear your Reefs with the bottle opener on the sole. I can assure you, those will impress her way more.

HIM: Those are out in the Hamptons.

ME: Maybe you should entertain her out there instead.

HIM: I'm going to have a little talk with her about my shoes.

ME: Whatever, just wear the rubber slippers while you're doing it.