If you loved the witty, awkward, and heartwarming charm of 'A Guide to Second Date Sex' (2019), you're in for a treat! This article curates 10 similar movies and shows that capture the same blend of romance, humor, and relatable dating mishaps. Whether you're a fan of modern love stories or enjoy the cringe-worthy yet endearing moments of new relationships, this list will keep you entertained.

The Break-Up (2006)
Description: A realistic portrayal of a relationship's end, focusing on the emotional fallout and the difficulty of letting go. Its blend of humor and heartache aligns with the reference film's approach.
Fact: The film's script was inspired by real-life breakup stories collected by the writers, giving it an authentic and relatable feel.


Forgetting Sarah Marshall (2008)
Description: A breakup comedy that balances humor with raw emotional honesty. It explores the messy aftermath of relationships and the awkwardness of moving on, resonating with the reference film's tone.
Fact: Jason Segel performed the full puppet musical sequence himself, which was inspired by his own love for puppetry and Jim Henson's work.


He's Just Not That Into You (2009)
Description: An ensemble romantic comedy that dissects modern dating dilemmas with humor and insight. It shares the reference film's focus on the awkward, often painful realities of love and relationships.
Fact: The film is based on a self-help book of the same name, which was inspired by a line from the TV show 'Sex and the City.'


The Five-Year Engagement (2012)
Description: A romantic comedy that explores the ups and downs of a long-term relationship, with a focus on the challenges of commitment. Its blend of humor and realism aligns with the reference film's tone.
Fact: The film's script was heavily improvised, with the actors given freedom to ad-lib many of their lines, adding to its naturalistic feel.


No Strings Attached (2011)
Description: This movie tackles the idea of casual relationships turning into something more serious, with a mix of humor and emotional depth. It mirrors the awkward yet endearing journey of navigating love and intimacy.
Fact: The film was originally titled 'Friends with Benefits,' but the title was changed to avoid confusion with the similarly themed movie released the same year.


Friends with Benefits (2011)
Description: A lighthearted take on the friends-with-benefits trope, filled with witty banter and genuine emotional moments. It captures the tension between physical attraction and emotional connection.
Fact: The film features several iconic locations in New York City, including Times Square and the High Line, adding to its vibrant urban aesthetic.


Love, Rosie (2014)
Description: A charming story about missed connections and the slow burn of love over time. Its mix of humor and heartfelt moments mirrors the emotional journey of the reference film.
Fact: The film is based on the novel 'Where Rainbows End' by Cecelia Ahern, who also wrote 'P.S. I Love You.'


Trainwreck (2015)
Description: A raunchy yet heartfelt comedy about a woman navigating love and self-discovery. Its bold humor and emotional depth resonate with the reference film's style.
Fact: The film marked Amy Schumer's first leading role in a major motion picture, and she also wrote the screenplay.


Sleeping with Other People (2015)
Description: A witty and honest take on modern relationships, exploring the blurred lines between friendship and romance. Its sharp dialogue and emotional authenticity echo the reference film's approach.
Fact: The film was shot in just 25 days, a remarkably short production schedule for a feature-length movie.


The Big Sick (2017)
Description: A romantic comedy that explores the complexities of modern relationships, blending humor with heartfelt moments. It delves into cultural differences and personal growth, much like the reference film.
Fact: The film is based on the real-life romance between comedian Kumail Nanjiani and his wife Emily V. Gordon, who co-wrote the screenplay together.
