When Nate hooked up with Diana Payne on Gossip Girl, it was kind of the worst.

Nate shouldn’t have been dating someone so manipulative and Diana shouldn’t have gone after someone so naive.

Nate and Diana were a terrible couple

Nate had multiple hookups with older women, one of them being Diana Payne.

This happened later on in the series, as Nate was attempting to find his own footing in the world after his father went to prison.

Nate and Diana met at a party in Los Angeles, where Nate pretended to own the home the pair were at so he could get in Diana’s pants.

While it worked, the encounter left Nate feeling embarrassed, as it was Diana’s home they were at the whole time.

This wasn’t the only time Nate and Diana hooked up with each other, though.

Nate found his way back to the Big Apple, where Diana shortly also appeared.

It’s clear that while the age gap was certainly there, the two had feelings for each other.

Neither could act on them, as Diana was helping fund The Spectator, the newspaper Nate was in charge of.

The toxic relationship with a superior at work certainly wasn’t going to lead the pair to the aisle.

Instead, there were countless moments that left viewers feeling cringy and icky inside.

What are your thoughts on this? Let us know in the comment section below.