The frustrating dating scenario of the 21st century is brimming with situationships, breadcrumbing, and, worst of all, red-flag boyfriends. Whether it is the narcissistic finance bro, insecure tech nerd, entitled coconut man, or Italian mamma’s boy, the variety of red-flag men is plenty. The peculiar thing about red flags is that they tend to be masked under the pretense of first impressions, and it takes quite some time — and trauma — to spot them. Realization eventually hits tenfold in the most unexpected moments, perhaps during an abrupt proposal or the sudden discovery of a sexual ick!
Movies have been brimming with red-flag men from the beginning of time who’ve conveniently escaped the tag due to the advantage of being viewed through rose-colored rom-com lenses. Whether Jack (Leonardo DiCaprio) from Titanic or Bryce Loski (Callan McAuliffe) from Flipped, the romance tropes and dramatic redemptions mask these men’s evident personality issues. But alas! We won’t let any problematic boyfriends escape our red flag detector as we dive into six movie boyfriends who didn’t deserve to date the gorgeous leading ladies they were paired with.
1. Nate Cooper | The Devil Wears Prada
Nate Cooper (Adrian Grenier) was a greater villain than Miranda Priestly (Meryl Streep) in The Devil Wears Prada. He was quite an insignificant character save for his red-flag behavior that gradually got tiresome and infuriating. He judges Andy (Anne Hathaway) for being dedicated to her job and gets annoyed when she starts dressing better to impress her boss. Nate is also wildly unsupportive — he lacks empathy and maturity as he overlooks the struggles and pressure her new job at Runway entails. He berates Andy for not giving him time instead of supporting and uplifting her during this stressful period.
The Devil Wears Prada is a cult classic movie that centers around Andy, a young graduate who travels to New York with aspirations to become a journalist. She starts working as an assistant to Type A Miranda Priestly, the editor of the city’s biggest magazine, Runway. The movie portrays her stressful albeit eye-opening journey, as she tackles the intricacies of working in high fashion.
Watch The Devil Wears Prada on Netflix
2. Fletcher Flemson | Bride Wars
Fletcher Flemson (Chris Pratt) from Bride Wars is another rom-com boyfriend with the biggest red flags. In a movie about wedding planning, viewers grew increasingly concerned for Emma (Anne Hathaway) as her fiancee turned irritable. He constantly undermined her decisions, didn’t show enthusiasm toward the wedding planning, and even his cheapskate proposal deserves a bombastic side-eye. Fletcher also criticizes Emma’s friendship with Liv (Kate Hudson) and passes snarky remarks about her job, so naturally, it is relieving when she breaks off the wedding.
Bride Wars is a popular rom-com about two childhood best friends, Liv and Emma, who’ve always dreamt of having picture-perfect weddings. Things get ugly when the venue they want to book only has two openings on the same day, which is unacceptable as they are each other’s maid of honor. The film explores how wedding planning can make women turn against each other and pull off the most despicable acts to get their way.
3. Dex | Something Borrowed
Dex (Colin Egglesfield) from Something Borrowed was a raging red flag, so it was quite infuriating that he got a happy ending. As if sleeping with his fianceé Darcy’s (Kate Hudson) best friend Rachel (Ginnifer Goodwin) wasn’t bad enough, he led Rachel on the whole time and strung her along as he struggled to make a choice. What’s most infuriating is that he continually acts like someone held a knife to his throat to date Darcy. He has a complete lack of regard for the consequences of his actions and that they could affect Rachel and Darcy’s friendship.
Based on Emily Giffin‘s novel of the same name, Something Borrowed is a romantic comedy that revolves around childhood best friends Rachel and Darcy. The duo are joined at the hip until a drunken night leads Rachel to sleep with Darcy’s fiancé Dex — whom she’s always had a crush on. Things get messy when Dex expresses that he has feelings for Rachel, too, as they struggle to break the news to Darcy.
Watch Something Borrowed on Netflix
4. Hardin Scott | After
Hardin Scott (Hero Fiennes Tiffin) from the After movie series is the most problematic character ever in a teen drama. The fact that this character got five movies worth of screen time is unfathomable, to say the least. While the brooding bad boy may seem like a good idea when you’re floating amid the myriad of teenage rom-coms, he’s the trophy boy of the red flag. Throughout the After movies, Hardin is portrayed as moody, possessive, and tastelessly reckless. He emotionally abuses Tessa (Josephine Langford) and projects his past traumas onto her as he fails to be a trustworthy boyfriend.
Based on Anna Todd’s popular After novels, the film series revolves around the tumultuous and toxic relationship between a young couple, Tessa Young and Hardin Scott. The series is wildly popular and has garnered massive fanfare. It currently consists of five movies, with another sequel and prequel in development.
5. Christian Grey | Fifty Shades of Grey
Christian Grey (Jamie Dornan) from the Fifty Shades film series was an obvious choice for this list. Apart from the fact that the man was into tasteless textbook BDSM, he also didn’t believe in the concept of boundaries. Not to forget that he exploited an inexperienced, naive virgin for his violent sexual endeavors. There’s a raging theme in movies and real life where the red flags of an exceptionally good-looking, wealthy man often go unnoticed owing to pretty privilege. Christian Grey dips at the sight of responsibility, finds unhealthy ways to deal with his trauma, and continually abuses his partner — physically and emotionally.
Fifty Shades of Grey is an erotic romance drama based on E. L. James‘ novel of the same name. It’s the first installment in the Fifty Shades film series, followed by its sequels Fifty Shades Darker and Fifty Shades Freed. The film revolves around the sadomasochistic relationship between college graduate Anastasia Steele (Dakota Johnson) and wealthy entrepreneur Christian Grey, as it takes viewers through the tumultuous ride of their unconventional dynamic.
Watch Fifty Shades of Grey on Netflix
6. Noah Flynn | The Kissing Booth
We end this list with the breathtaking male lead with raging anger issues, Noah Flynn (Jacob Elordi) from The Kissing Booth. Despite being charming and protective, he is an aggressive and possessive boyfriend, which makes him a red-flag character. He lacks emotional maturity and is often seen acting impulsively in the most out-of-pocket ways. It’s concerning to watch Elle (Joey King) continue to be blindly in love with him as she fails to look beyond his abs to recognize his inherent personality issues.
The Kissing Booth is a popular teen romcom that took Netflix by storm in 2018. The film revolves around inseparable childhood best friends Elle and Lee (Joel Courtney), whose friendship is tested when she has a secret relationship with his older brother and bad boy, Noah Flynn. Owing to its massive popularity, the movie boasts two sequels, The Kissing Booth 2 and The Kissing Booth 3. Also, don’t forget to check out this guide on 7 worst boyfriends in Sex and the City!
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