Over the course of television history, there have been countless romantic relationships among viewers’ favorite characters. Some of them get fans swooning, wishing that the perfect boyfriend could exist in real life, while others throw relationship red flags left and right.
Even though these boyfriends may be some of viewers’ favorite characters, it’s hard to deny denied that they have some seriously toxic traits. Whether they’re insatiably clingy, controlling, or serial cheaters, these television boyfriends shouldn’t be anyone’s ideal men.
Chuck Bass – Gossip Girl (2007-2012)
Chuck and Blair are one of the best couples on Gossip Girl with some iconic scenes. Their electric chemistry and Chuck’s undying devotion are part of what makes them so strong. However, the subject of Chuck’s glaring red flags can’t be avoided, and for a long time, he was a very unhealthy boyfriend.
At the top of the list is the fact that he did, in fact, try to “sell” Blair to his uncle to save his hotel. To make matters worse, he originally thinks she went through with his plan and is angry with her, which is very manipulative. On top of that, he has a history of aggressive playboy behavior and drug use, and he spent many episodes lying to Blair about his true feelings for her to “avoid hurting her.”
Dean Forester – Gilmore Girls (2000-2007)
Many fans might romanticize Dean because he was Rory’s first boyfriend on Gilmore Girls, but his behavior from start to finish is cringy at best and appalling at worst. Dean is an intensely controlling and needy boyfriend, calling Rory’s house 14 times in 15-minute intervals even when Lorelai told him she wasn’t home yet.
Instead of giving opinions about her writing, he would say things like, “You know about that stuff more than I do,” even though they started talking because she realized he was a reader like her. Furthermore, he ends up cheating on his wife, Lindsay, with Rory later on and constantly acts like Lindsay’s affection is too much and her efforts to please him aren’t enough.
Joe Goldberg – You (2018-present)
Even with the murdering and stalking completely off the table, Joe is still a toxic boyfriend on You. He routinely idealizes women to an entirely unrealistic point, and when he discovers that they are, in fact, just normal human beings, he becomes uninterested in them.
Joe is also a huge hypocrite with Love and constantly attacks her for doing things that he’s done in the past and continues to do. Additionally, he gaslights her into thinking she’s being ridiculous when she accuses him of stalking their neighbor. He has gigantic commitment issues, and even leaves their baby on a friend’s doorstep, moving on to a new life where he can chase another girl across France.
Ian Gallagher – Shameless (2011-2021)
Mickey is the best thing to happen to Ian Gallagher on Shameless, but that doesn’t mean their relationship is healthy. They’ve each done wrong, but Ian has waved some very red flags, even into the last season.
To start, Ian went through a phase of cheating on Mickey repeatedly and never really expressed any remorse for it. This was solidified when he told Mickey that he assumed their marriage would be open, even though they had been monogamous leading up to it. That lack of communication is another red flag. Instead of discussing things beforehand, Ian just assumes that things will work out.
Ross Geller – Friends (1994-2004)
Ross and Rachel from Friends are a television couple that just about everyone knows, but they should definitely not be idealized. Their constant splits and reconciliations are toxic enough, not to mention the whole “break” debacle.
Ross is a walking red flag in many aspects of his life. He says another woman’s name at the altar during his wedding, dated one of his students when he was a professor, and reprimanded his son for wanting to play with a Barbie, using some very misogynistic language about them being “for girls.”
Hot Priest – Fleabag (2016-2019)
No one can say that the sparks weren’t flying between Fleabag and the Hot Priest or that she was not living out some fantasy that belongs in the pages of an adult novel. They were, after all, the two funniest Fleabag characters. That being said, many things set them up for ultimate failure on his part.
Firstly, he committed his life to the church as an escape from a past full of darkness and countless love affairs, and anyone running into the priesthood from that sort of trauma is struggling with their self-identity and isn’t in the right mindset to treat someone healthily. Secondly, he very plainly has a drinking problem, taking out the G&Ts the moment it strikes noon and getting drunk in the church office.
Rafael Solano – Jane The Virgin (2014-2019)
It may sound romantic to have parents get together before their baby is born, even if the baby was a bizarre medical mishap between two almost-strangers. But not only did Rafael romantically pursue Jane the Virgin‘s titular heroine while she was engaged to Michael, he jumped into a relationship with her right after the engagement broke off.
Rafael routinely pushes the gas, then pulls away. After starting their relationship, he reacts very negatively when he learns Jane is a virgin. Fresh off the end of her relationship with Michael, Rafael tries to propose to her himself before pulling away again. Rafael never grows as a person in Jane the Virgin and even got Michael fired, proving that just because it’s romantic doesn’t mean it’s healthy.
Andy Dwyer – Parks & Recreation (2009-2015)
Andy and April may be a match made in weird heaven on Parks and Recreation, but that doesn’t make up for the fact that Andy is mostly a man-child who is incapable of doing almost anything for himself. Plus, their relationship started with Andy calculating April’s age to see if dating her was “OK” or not.
Andy is the opposite of responsible. He doesn’t manage money well at all and can barely handle simple tasks at work or in his relationship. He also has a penchant for being impulsive, reckless, and clingy, basically stalking Ann after their breakup and living outside of her house in a pit. His saving grace is that he does support April in her dreams, but that should be a given in any relationship.
Mr. Big – Sex And The City (1998-2004)
Big gives Carrie hot and cold over and over again on Sex and the City, wanting her but then pushing her away emotionally. It seemed that he always wanted her when he couldn’t have her and lost interest when she was willing to be with him, which is a huge red flag and a reason Carrie and Big’s relationship was so toxic.
After being unwilling to commit to Carrie over two years, Big marries someone he knew for five months, then initiates an affair with Carrie during the marriage. After pursuing her while she’s in a relationship and successfully winning her back, he gets cold feet before going through with their wedding in the feature film.
Ezra Fitz – Pretty Little Liars (2010-2017)
First and foremost, any high-school teacher wanting to date a student is a predatory red flag. Regardless of Aria’s efforts, it was Ezra’s responsibility as the adult and the teacher to shut it down, but he repeatedly put himself in risque situations with her and acted on his inappropriate feelings.
The words “even though this doesn’t look right, it always felt right” are definitely the sketchiest choice when talking to your high-schooler girlfriend. Ezra gets jealous when Aria tries to move on, but he feels guilty when she tries to make things work, all of which are giant red flags.
