Boss texts that she’ll fire him if he kisses his date

So, I think this is a TV show. I saw it long ago, maybe between 2007 and 2015. Vague, I know. It was colour.

So, there’s this guy and a girl in a bar. The girl is a nerd and is wearing black glasses. She’s a pudgy. The guy is thin. Both are white. So, the boss of the guy, is keeping an eye on him while they’re talking. I think she likes him, or maybe was dating him before.

Then, the girl and the guy stand on their back to each other and start walking forward.. they’re playing some kind of a game. The guy asked, “Why are we doing this?”, the girl says, “I don’t go out much.”

In the next scene, they are talking and he gets a text from his boss, who is observing them from a distance. The text says, “If you kiss her, you’re fired.” The girl leans in to kiss her and he moves away. She is really upset and runs away crying. I guess, she felt that he rejected her.

Can you tell me which show this is?

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