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Ted Lasso’s Depiction of Serial Cheaters Is Too Accurate and All Too Familiar

Rebecca, Zava, and Rupert stand in a hallway, smiling at each other tensely.

Out of all the characters in Ted Lasso, Rupert (Anthony Head) might be the only one who’s irredeemable. He’s too slimy, too awful, and too narcissistic to have a believable change of heart. In one poignant scene in the latest episode, “(I Don’t Want to Go to) Chelsea,” Rebecca shares some insight into his psychology—and as someone who once dated a guy as bad as Rupert, I saw a lot of myself in her story.

This article contains mild spoilers for Ted Lasso season 3, episode 2.

While sitting in the stands at Richmond’s game against Chelsea, Rebecca spots Rupert buttering up Zava, the football prodigy every team is hoping to sign. Rebecca angrily tells Keeley about Rupert’s way of getting people in his thrall, describing how he left his wife and pursued Rebecca by chatting with her at the bar where she worked every night for six weeks. “By that point, I just felt so lucky because he wanted me,” she says, describing how she agreed to go out with him despite his being married. “He made me feel special. Chosen.”

Oof. Rebecca might as well have been telling the story of one of my worst relationships.

How narcissists sink their claws into you

Before I tell this story, note that there’s a huge difference between polyamory and cheating. There are some very good arguments to be made against monogamy, but those arguments don’t negate the emotional devastation of finding out that a supposedly committed partner has tossed you aside.

I met a guy in college. He was dating another girl at the time, so I assumed he was off limits, but then he started to take an interest in me. One day, we spotted each other across the quad, both our faces lit up at the same time, and we hurried to meet each other in the middle. Within a couple of weeks, we were dating, and he showered me with love: He drew portraits of me, gave me expensive (for a college student) gifts, and spent hours with me in deep conversation. I was so swept up in the magic of it all that I didn’t notice how his previous girlfriend had faded from view.

I tend to be pretty oblivious when it comes to figuring out what people are up to behind my back, so I didn’t find out for months that he was still dating her when he asked me out. He never admitted to it. I found out through the campus rumor mill, and hastily tamped down my embarrassment and guilt. He’d done a bad thing, but hopefully she had moved on, and the two of us were perfect for each other. Surely he could be forgiven for making a mistake when he was following his heart?

I felt so stupid for not realizing that I was only one small part of his larger pattern of wooing women and then getting bored with them. After we’d been together for a while, he started flirting with other girls right in front of me—but in playful ways that gave him plausible deniability. Was he actually flirting with so-and-so? Of course not! They were just bonding over a song they both liked! Or studying together! Or playing full-contact keep-away with her keys! (Like I said, I can be pretty oblivious about these things, especially when someone is actively gaslighting me.)

Eventually, a mutual friend pointed out that my boyfriend didn’t seem to respect me at all. She noticed how, when we entered a building, he didn’t bother to hold the door open for me. Holding the door for someone isn’t some heteronormative display of chivalry—it’s common courtesy, and he couldn’t even be bothered to show me that level of decency anymore.

You can see where this is going. Of course he cheated on me. After we broke up, I found comments he’d exchanged with his new crush on a blog post, in which they gushed over how they were kindred spirits. That deep, spiritual connection apparently didn’t last long, though, because he swiftly got bored of her, too.

Because that’s the psychology of the serial cheater. To narcissists like Rupert and my ex, every person around them is either a prize to be won or an obstacle to knock down. They can’t stay with one person, because they’re incapable of forming real connections with people. All of this is doubly true when we’re talking about a narcissistic man dealing with women.

You can tell this episode dredged up some old stuff for me, which is a testament to how well Rupert’s character is written. He may be utter scum, but he’s very believable. He’s also a cautionary tale: if someone woos you while they’re seeing someone else, it’s not because they’ve realized you’re their soulmate. That twin flame vibe they’re giving off is just a plain ol’ red flag.

(featured image: Apple TV+)

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Julia Glassman (she/they) holds an MFA from the Iowa Writers' Workshop, and has been covering feminism and media since 2007. As a staff writer for The Mary Sue, Julia covers Marvel movies, folk horror, sci fi and fantasy, film and TV, comics, and all things witchy. Under the pen name Asa West, she's the author of the popular zine 'Five Principles of Green Witchcraft' (Gods & Radicals Press). You can check out more of her writing at