If you enjoyed the quirky humor and unconventional take on relationships in I Do... Until I Don't (2017), you're in for a treat. This article explores 10 similar movies and shows that blend comedy, romance, and a dash of existential questioning—perfect for fans of witty, offbeat storytelling.

The Break-Up (2006)
Description: This film explores the complexities of modern relationships and the challenges of maintaining love after the initial spark fades, focusing on the emotional rollercoaster of a couple navigating post-breakup dynamics.
Fact: The movie was originally conceived as a drama but was rewritten as a comedy to appeal to a broader audience. It was filmed in Chicago, showcasing the city's vibrant neighborhoods.


The Switch (2010)
Description: A quirky take on unconventional family dynamics and the idea of destiny in relationships, with a mix of humor and emotional depth.
Fact: The movie was originally titled 'The Baster,' referencing the artificial insemination plot point, but was changed to avoid confusion.


He's Just Not That Into You (2009)
Description: A multi-narrative romantic comedy that delves into the anxieties and miscommunications of dating, highlighting how people interpret romantic signals differently.
Fact: The film is based on a self-help book of the same name. It features an ensemble cast with interconnected storylines, a popular narrative style in romantic comedies.


The Five-Year Engagement (2012)
Description: A humorous yet poignant exploration of how life's unpredictability can delay or derail even the most committed relationships, emphasizing patience and compromise.
Fact: The script was partially inspired by the real-life experiences of the film's writers, who faced delays in their own engagements.


How to Be Single (2016)
Description: A vibrant exploration of single life in the city, celebrating independence while also examining the search for meaningful connections.
Fact: The movie features a cameo by the author of the book it's based on, Liz Tuccillo, who also wrote for 'Sex and the City.'


No Strings Attached (2011)
Description: A lighthearted yet insightful look at friends who attempt to keep their relationship purely physical, only to discover that emotions are harder to control than they thought.
Fact: Natalie Portman and Ashton Kutcher had known each other for years before filming, which helped their on-screen chemistry.


Friends with Benefits (2011)
Description: This movie tackles the idea of casual relationships and the blurred lines between friendship and romance, with witty dialogue and a modern take on love.
Fact: Justin Timberlake and Mila Kunis performed most of their stunts, including the iconic flash mob scene in Times Square.


Love, Rosie (2014)
Description: A charming story about lifelong friends who struggle to admit their feelings for each other, filled with missed opportunities and heartfelt moments.
Fact: The film is based on the novel 'Where Rainbows End' by Cecelia Ahern. It was shot in various locations, including Dublin and Toronto.


The Other Woman (2014)
Description: A comedic yet empowering tale about women bonding over shared romantic betrayal, blending humor with themes of friendship and self-discovery.
Fact: The film's beach house scenes were shot in the Hamptons, a popular location for romantic comedies.


The Big Sick (2017)
Description: A heartfelt story that blends romance and cultural differences, showing how love can endure even through serious life challenges and family expectations.
Fact: The film is based on the real-life romance between its writers, Kumail Nanjiani and Emily V. Gordon, including Gordon's medically induced coma.
