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100+ Movies like Crazy, Stupid, Love.

3.6
2011 Comedy, Drama, Romance

Crazy, Stupid, Love. is a romantic comedy-drama that explores the complexities of love, relationships, and self-discovery. The movie follows Cal Weaver, a middle-aged man navigating the aftermath of his wife's infidelity and subsequent divorce. With the help of a womanizing mentor, Cal embarks on a journey of reinvention, learning to embrace his newfound confidence and attracting multiple romantic interests. Meanwhile, his son Robbie grapples with his own romantic pursuits, and a tangled web of connections emerges, involving Cal's estranged wife, his mentor's love interest (who happens to be Cal's daughter), and a series of hilarious misunderstandings. This page offers a curated selection of movies that delve into similar themes of love, heartbreak, self-discovery, and the intricate dynamics of modern relationships, providing a relatable and entertaining viewing experience.

Tempting Fate

Tempting Fate

3.0
2019

Both "Crazy, Stupid, Love." and "Tempting Fate" explore themes of infidelity and the breakdown of marriages. In "Crazy, Stupid, Love.", Cal's wife Emily has an affair that leads to their separation, while in "Tempting Fate", Gabby has an affair with Matt that results in her becoming pregnant and her husband Elliott wanting a divorce. The movies parallel each other in depicting the emotional turmoil and consequences that arise from infidelity, as well as the characters' attempts to reconcile and potentially rebuild their relationships. Additionally, both films involve younger people (Jacob and Matt) who initially represent a carefree, promiscuous lifestyle that contrasts with the committed relationships of the older characters, but who ultimately undergo personal growth and find meaning in more serious romantic connections.

Your Place or Mine

Your Place or Mine

3.2
2023

Both "Your Place or Mine" and "Crazy, Stupid, Love." revolve around long-time friends who secretly harbor romantic feelings for each other. In "Crazy, Stupid, Love.", Cal and Emily are a married couple who separate due to Emily's affair, while in "Your Place or Mine", Debbie and Peter are best friends who had a one-night stand years ago. The plots follow their journeys of self-discovery and personal growth, with Cal embracing a new lifestyle under Jacob's guidance, and Peter helping Debbie's son Jack open up. Ultimately, Cal and Emily rekindle their relationship, while Debbie and Peter finally confess their love for each other after years of repressing their feelings. The movies explore themes of love, friendship, family, and second chances through the lens of complex relationships and character arcs.

Some Kind of Beautiful

Some Kind of Beautiful

2.8
2015

Both "Some Kind of Beautiful" and "Crazy, Stupid, Love." revolve around middle-aged men navigating romantic relationships and family dynamics after a major life event - divorce in "Crazy, Stupid, Love." and an unexpected pregnancy in "Some Kind of Beautiful". The protagonists, Cal and Richard, receive guidance from younger male mentors (Jacob and Richard's father) on how to attract women, leading them to engage in casual sexual encounters. However, they ultimately realize the importance of committed relationships and reconciling with their former partners/wives. The movies explore themes of love, fidelity, parenthood, and personal growth through comedic and heartfelt storylines involving complex family relationships and romantic entanglements. The narratives interweave multiple character arcs and subplots, culminating in emotional resolutions where the protagonists embrace maturity and prioritize their families.

Chaos Theory

Chaos Theory

3.1
2007

Both "Crazy, Stupid, Love." and "Chaos Theory" revolve around marital issues and infidelity that lead to the breakdown of relationships. The central plot involves a husband (Cal in "Crazy, Stupid, Love." and Frank in "Chaos Theory") whose wife (Emily and Susan, respectively) has an affair, leading to separation and the husband's journey of self-discovery and attempts to win back his wife. This journey involves the husband gaining confidence and dating other women, as well as misunderstandings and complications arising from these new relationships. The movies also explore themes of fatherhood, with the husbands' relationships with their children (Robbie and Jesse) playing a significant role. Both films feature a womanizer character (Jacob and Buddy) who initially serves as a mentor to the husband but later develops a romantic interest in the husband's daughter, creating conflict. The stories culminate in the husbands realizing their love for their wives and attempting to reconcile, while also addressing the complexities of their relationships with their children and the other characters involved in the infidelity storylines.

Meet Bill

Meet Bill

3.0
2007

Both "Crazy, Stupid, Love." and "Meet Bill" center around middle-aged men going through marital crises and personal transformations. The protagonists, Cal Weaver and Bill Anderson, experience their wives' infidelity which leads to separation and a journey of self-discovery. They receive guidance from unlikely mentors, Jacob Palmer and "the Kid" respectively, who help them regain confidence and attract women. The movies explore themes of love, relationships, family dynamics, and finding one's identity. Both feature comedic subplots involving the protagonists' children navigating their own romantic interests. The climax involves a chaotic gathering where past conflicts converge, leading to physical altercations. Ultimately, the protagonists gain newfound perspectives on life and relationships, reconciling with their wives or moving on with optimism.

Sol Goode

Sol Goode

2.1
2003

Both "Crazy, Stupid, Love." and "Sol Goode" revolve around male protagonists who are immature womanizers and struggle with commitment, but undergo transformations to become more responsible and open to genuine relationships. The movies parallel each other in the following ways: - The main characters (Cal and Sol) are middle-aged men who initially live carefree, irresponsible lifestyles focused on casual sex and avoiding serious relationships. - They receive guidance from younger male mentors (Jacob and Happy) who teach them how to be successful with women, but these mentors also eventually mature and pursue meaningful relationships themselves. - The protagonists' journeys involve reconnecting with ex-partners (Emily and Chloe) and realizing their true feelings, leading to attempts to rekindle those relationships. - Family relationships and parental pressures play a role in motivating the protagonists to change their ways and become more mature. - Both movies feature subplots involving younger characters (Robbie and Jessica, Justin and Brenda) navigating romantic relationships and growing up. - The climaxes involve chaotic confrontations where the protagonists' pasts catch up with them, but they ultimately embrace commitment and lasting love.

About Last Night

About Last Night

3.0
2014

Both "About Last Night" and "Crazy, Stupid, Love." revolve around the themes of relationships, breakups, and finding love again. They follow the story arcs of couples who separate due to infidelity or lack of commitment, and the male protagonists' journeys of self-discovery and growth as they navigate the dating world. The plots parallel each other with the men receiving guidance from womanizing friends on how to attract women, leading to casual flings that ultimately prove unfulfilling. The narratives culminate in the men realizing their true feelings for their ex-partners and attempting to reconcile, while their friends also find meaningful relationships. The movies explore the complexities of modern romance through comedic yet poignant lenses.

Made of Honor

Made of Honor

3.2
2008

Both "Crazy, Stupid, Love." and "Made of Honor" revolve around a male protagonist who is initially oblivious to the romantic feelings of his close female friend. In "Crazy, Stupid, Love.", Cal's wife Emily has an affair, leading to their separation, while in "Made of Honor", Tom remains emotionally unavailable to his best friend Hannah. The movies follow the protagonists' journeys of self-discovery and personal growth, aided by mentors (Jacob in "Crazy, Stupid, Love." and Tom's friends in "Made of Honor") who help them become more confident and desirable. Ultimately, the protagonists realize their love for their female friends (Emily and Hannah, respectively) and make grand romantic gestures to win them back, overcoming obstacles like other romantic interests (David in "Crazy, Stupid, Love." and Colin in "Made of Honor"). Both films explore themes of love, friendship, and the complexities of modern relationships through comedic yet heartfelt narratives.

Newness

Newness

3.0
2017

Both "Crazy, Stupid, Love." and "Newness" explore themes of relationships, infidelity, and finding love in the modern dating world. The central characters in both movies experience relationship troubles - Cal's wife Emily has an affair in "Crazy, Stupid, Love.", while Martin and Gabriella in "Newness" open up their relationship to others. The movies follow the characters as they navigate the complexities of dating, with mentors like Jacob in "Crazy, Stupid, Love." and the open relationship dynamic in "Newness" guiding them. Ultimately, the movies show the characters realizing the importance of commitment and true love, with Cal trying to win Emily back and Martin and Gabriella reconciling after exploring non-monogamy. The movies parallel each other in their portrayals of modern romance, infidelity, and the journey to find meaningful connections.

The 40 Year Old Virgin

The 40 Year Old Virgin

3.2
2005

Both "The 40 Year Old Virgin" and "Crazy, Stupid, Love." center around middle-aged men struggling with relationships and sexuality. The protagonists, Andy and Cal, receive guidance from younger male friends who are more experienced with women. This mentorship helps them gain confidence and dating skills, leading to romantic encounters. However, their newfound promiscuity initially strains their primary relationships with Trish and Emily. Ultimately, the men realize the importance of committed love and work to reconcile with their partners. The films explore themes of masculinity, self-improvement, and the complexities of modern romance through comedic yet heartfelt narratives.

The Last Summer

The Last Summer

3.0
2019

Both "Crazy, Stupid, Love." and "The Last Summer" explore the themes of love, relationships, and personal growth through interconnected storylines involving groups of young people. The movies follow multiple character arcs as they navigate romantic entanglements, breakups, and new relationships during pivotal transitional periods in their lives - divorce for Cal in "Crazy, Stupid, Love." and the summer before college in "The Last Summer". The ensemble casts allow the films to portray a range of relationship dynamics, from long-term marriages to casual flings, while characters learn lessons about love, self-discovery, and moving forward. The movies employ comedic tones and moments of levity amidst the more dramatic romantic plotlines.

Concussion

Concussion

2.6
2013

Both "Crazy, Stupid, Love." and "Concussion" explore themes of dissatisfaction in long-term relationships and the desire to seek new experiences and connections outside of marriage. The main characters, Cal in "Crazy, Stupid, Love." and Abby in "Concussion", undergo personal transformations and rediscover their confidence after feeling unfulfilled in their marriages. They engage in casual sexual encounters as a form of escape and self-discovery, leading to complications in their primary relationships. The movies parallel each other in depicting the struggles of maintaining intimacy and passion in committed partnerships, as well as the consequences of infidelity. Ultimately, both stories examine the characters' journeys to rekindle the spark in their marriages or move on to new relationships that better fulfill their needs.

My Awkward Sexual Adventure

My Awkward Sexual Adventure

3.5
2012

Both "My Awkward Sexual Adventure" and "Crazy, Stupid, Love." revolve around a man going through a relationship crisis and seeking to improve his romantic/sexual prowess with the help of an unconventional mentor. In "Crazy, Stupid, Love.", Cal's wife Emily leaves him, prompting the womanizer Jacob to teach Cal how to pick up women. Similarly in "My Awkward Sexual Adventure", Jordan's girlfriend Rachel leaves him due to his sexual ineptitude, leading him to enlist the stripper Julia to broaden his sexual horizons. The two men undergo a transformation, gaining confidence and success with women, though ultimately realizing their true feelings lie with their original partners. The movies parallel each other in the themes of relationships, self-improvement, and finding one's true love through an unconventional journey of sexual exploration guided by an unlikely mentor figure.

On the Line

On the Line

2.4
2001

Both "On the Line" and "Crazy, Stupid, Love." revolve around a man's romantic struggles and journey to find love. In "Crazy, Stupid, Love.", Cal's wife Emily leaves him after an affair, leading him to seek help from a womanizer Jacob to regain his confidence and dating skills. Similarly, in "On the Line", Kevin is a man who meets a woman named Abbey but struggles to reconnect with her, resorting to public pleas and dating other women to find her. The movies share themes of heartbreak, self-improvement, and the pursuit of a romantic connection. They also feature subplots involving the protagonists' friends and family members navigating their own relationships. Both films culminate in grand romantic gestures by the lead characters to win back or unite with their love interests.

Little Children

Little Children

3.5
2006

Both "Crazy, Stupid, Love." and "Little Children" explore themes of infidelity, marital problems, and the pursuit of new relationships amidst crumbling marriages. The plots center around suburban couples whose relationships are strained, leading them to seek intimacy and connections outside of their marriages. In "Crazy, Stupid, Love.", Cal's wife Emily has an affair, leading to their separation and Cal's journey of rediscovering himself and dating other women. Similarly, in "Little Children", Sarah's marriage to Richard deteriorates due to his pornography addiction, leading her to an affair with Brad. Both movies depict the complexities of modern relationships, the temptations of infidelity, and the consequences of acting on those temptations. The narratives interweave multiple storylines involving different couples and their struggles with commitment, desire, and the search for fulfillment.

Just Go with It

Just Go with It

3.3
2011

Both "Just Go with It" and "Crazy, Stupid, Love." revolve around middle-aged men who are dishonest about their relationship status to attract women, leading to increasingly convoluted lies and schemes involving fake spouses and families. The protagonists eventually realize their mistakes and pursue genuine relationships with women they truly care about - Danny with Katherine in "Just Go with It", and Cal with his estranged wife Emily in "Crazy, Stupid, Love." The movies explore themes of love, commitment, and the importance of honesty in relationships through comedic storylines involving mistaken identities and farcical situations. The protagonists' journeys of self-discovery and growth parallel each other as they learn to let go of their deceptive ways and open themselves up to meaningful connections.

It's Complicated

It's Complicated

3.3
2009

Both "Crazy, Stupid, Love." and "It's Complicated" explore themes of divorce, infidelity, and the complexities of modern relationships. The central plot revolves around a middle-aged couple whose marriage is disrupted by an affair, leading to separation and the exploration of new romantic interests. The husbands in both films, Cal and Jake, engage in affairs and attempt to rediscover their confidence and desirability. The wives, Emily and Jane, grapple with the aftermath of betrayal while navigating their own desires and potential new relationships. The films parallel each other in depicting the emotional turmoil, mistakes, and eventual growth that can arise from marital strife. Both stories also involve subplots centered around the couple's children and their own romantic endeavors, reflecting the ripple effects of parental relationships on family dynamics.

Landline

Landline

3.0
2017

Both "Crazy, Stupid, Love." and "Landline" explore themes of infidelity, strained marriages, and family dynamics. In "Crazy, Stupid, Love.", Cal's wife Emily has an affair, leading to their separation and Cal's journey of rediscovering himself. Similarly, in "Landline", the parents Pat and Alan are dealing with Alan's affair, which is discovered by their daughters Dana and Ali. The movies parallel each other in depicting the fallout from the affairs, the impact on the families, and the characters' attempts to navigate their relationships. Additionally, both films feature subplots involving the children's romantic entanglements, with Robbie pursuing his babysitter Jessica in "Crazy, Stupid, Love." and Dana engaging in an affair of her own in "Landline". The overall narrative arcs revolve around the families confronting the infidelity, the emotional turmoil it causes, and the efforts to reconcile or move forward.

The Meddler

The Meddler

3.0
2016

Both "Crazy, Stupid, Love." and "The Meddler" explore themes of relationships, family dynamics, and finding love and purpose in life after major life events. The central characters are middle-aged individuals navigating the aftermath of divorce/widowhood and seeking to rebuild their lives and connections with their adult children. The plots follow their journeys of self-discovery, developing new romantic interests, and mending strained familial bonds through humorous and heartwarming situations. The movies parallel each other in depicting the challenges of moving on from past relationships while maintaining strong family ties, ultimately delivering uplifting messages about embracing change and finding fulfillment.

The Stepford Wives

The Stepford Wives

2.8
2004

Both "Crazy, Stupid, Love." and "The Stepford Wives" explore themes of relationships, gender roles, and personal transformation. In "Crazy, Stupid, Love.", Cal undergoes a transformation from a downtrodden divorced man to a confident womanizer with the help of Jacob, mirroring how the wives in "The Stepford Wives" are transformed into submissive housewives through technological means. Both films feature a central character (Cal and Joanna) who initially struggles with their identity and relationships but ultimately finds empowerment and self-acceptance. The movies also depict the complexities of marriage, infidelity, and the pursuit of happiness within societal expectations. Additionally, they incorporate elements of comedy and satire to comment on gender dynamics and societal norms.