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Cougar Town Requests

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Imagine taking Bobby Cobb out for a nice dinner.


You and Bobby hadn’t been dating for very long. You’d been on enough dates to be considered an item, but not enough that you knew everything about each other. Every date you’d been on so far had been pretty low-key; mostly just hanging around together.

Because of that, you wanted to switch it up. To put it kindly, you were more financially stable than Bobby and you decided to take him out to a nicer restaurant than he’d been to in a while.

“Is this one of those places with a dress code? Do I have to wear a tie?”

“It’s not that nice, Bobby. Just wear something that doesn’t have any stains or holes.”

You’d made a reservation and decided to pick him up. It was a little too far for a golf cart to be sufficient. He was dressed as if he were heading to a funeral, but he did look good. He held your hand for nearly the entire ride. He only let go when he was getting animated while telling a story.

During dinner, Bobby gave you a warm smile. “Hey, Y/N, I appreciate this. I don’t usually get taken to places like this.”

“Are you enjoying it? Do you want to do things like this more often?”

“Yeah, yeah I do.”