When Rufus wasn’t busy trying to be the best dad he possibly could be to Dan and Jenny on Gossip Girl, he was also pursuing romance in his free time.

But truthfully, some of his romantic connections on the show were incredibly toxic. Here’s a ranking.

Bex Simon.

Bex is one of the less toxic romantic partners Rufus had on Gossip Girl since they only went on a small handful of dates. It got a tad toxic when he accidentally got her name confused with another woman named Bryn who he was attracted to as well. Bex and Rufus were on the same page when it came to their love for art, but their timing was never right.

Lisa Loeb.

Lisa is the woman Rufus ended up married to at the end of Gossip Girl There wasn’t anything inherently toxic about her, but their pairing came across as extremely random. There was no buildup leading viewers to have a better understanding of why Rufus and Lisa would end up together. The lack of buildup turned their marriage into something confusing and weird for viewers.

Alison Humphrey.

The number one detail that made Alison such a toxic ex-wife to Rufus is that she was a cheater. She left him, Dan, and Jenny in Brooklyn to relocate to Hudson where she started dating a new boyfriend. Rufus was still holding on to hope that he’d be able to reconcile with Alison someday, but that was nipped in the bud and he ended up heartbroken.

Lily van der Woodsen.

The relationship between Lily and Rufus seemed like it was built for the long-haul, but ultimately, they crashed and burned. There was a lot of toxicity between Lily and Rufus, especially to wards the end. Lily lied to Rufus about many things, and her lies were always outrageous. She lied about birthing and giving up their baby up for adoption. Later, she lied about spending the summer with her ex-husband, William van der Woodsen, as she was seeking cancer treatments. Rufus definitely couldn’t trust Lily at all.

Ivy Dickens.

The most toxic connection Rufus had on Gossip Girl was with Ivy. Ivy only started hooking up with him as a ploy to get revenge against Lily, and she never actually had real feelings for Rufus. Rufus made the stupid decision to pursue a connection with her, even though she was way too young for him. Another reason Rufus and Ivy should have never started hooking up is that Ivy also briefly tried dating his son, Dan. Everything about Rufus and Ivy‘s connection was wildly inappropriate and strange.

Which of Rufus‘s love interests on Gossip Girl was the most toxic in your opinion? Do you feel like he should have had a different ending with a different wife? Let us know your thoughts in the comment section below.