These are my recommendations for films and movies similar to He’s Just Not That Into You. Bear in your mind that this list is in no particular order.
When Brooke (Jennifer Aniston), an art dealer, and Gary (Vince Vaughn), a tour-bus driver, finally call it quits in their relationship, neither is willing to move out of their shared condo. With their friends suggesting a series of underhanded tactics that fail to get either Brooke or Gary to cave in, the only solution is to become hostile roommates.
Abby Richter (Katherine Heigl) is a lovelorn TV producer who, despite a long and arduous search for the perfect mate, is hopelessly single. The battle of the sexes heats up when her employers team her up with Mike Chadway (Gerard Butler), an opinionated TV celebrity who plans to put Abby through the wringer to prove his own theories about what makes men and women tick.
Lisa Jorgenson’s (Reese Witherspoon) entire life has been defined by softball, but at 31, she is deemed too old to play and cut from the team. After being cast adrift, she begins a fling with Matty (Owen Wilson), a charming womanizer who plays professional baseball. About the same time, she goes on a blind date with George (Paul Rudd), a businessman on the hook for stock fraud. Caught in a romantic triangle with the two men, Lisa ponders the meaning of love.
Irresponsible party girl Maggie (Cameron Diaz) is kicked out of her father’s (Ken Howard) and stepmother’s (Candice Azzara) home, where she lives for free, and is taken in by her hard-working sister, Philadelphia lawyer Rose (Toni Collette). After Maggie’s disruptive ways ruin her sister’s love life, Rose turns her out as well. But when their grandmother, who they never knew existed, comes into their lives, the sisters face some complicated truths about themselves and their family.
Always shy of commitment, Tom (Patrick Dempsey) lives as a serial dater. Hannah (Michelle Monaghan), his best friend, has wanted to marry and now has found Mr. Right — just as Tom realizes he really loves Hannah. When she asks him to be in her bridal party, Tom seizes the opportunity to prevent the nuptials and woo her himself.
Tom (Ashton Kutcher) and Sarah (Brittany Murphy) are two lovebirds from different worlds. He’s an average guy with a fondness for beer who works a low-level job, while she’s an aspiring writer from a wealthy and cultured family. The disapproval of family and friends doesn’t prevent the pair from marrying, but their disastrous honeymoon in Italy, with an unwelcome appearance by Sarah’s ex-boyfriend, Peter (Christian Kane), nearly succeeds in tearing them apart
Daphne Wilder (Diane Keaton) is the proud mother of three women: Milly (Mandy Moore), Maggie (Lauren Graham) and Mae (Piper Perabo), and her love for her offspring knows no bounds. Because her youngest, always chooses the wrong man, she decides to take action to prevent Milly from repeating the mistakes of the past. Dating disaster ensues when Daphne tries to achieve her goal by placing an online personal ad for Milly.
During a wild vacation in Las Vegas, career woman Joy McNally (Cameron Diaz) and playboy Jack Fuller (Ashton Kutcher) come to the sober realization that they have married each other after a night of drunken abandon. Besides that, there is a huge jackpot at stake. An implacable judge freezes the prize money and refuses to grant an annulment, so Joy and Jack must try to make their impromptu marriage work.
With the wedding of her younger sister (Amy Adams) fast approaching, Kat Ellis (Debra Messing) faces the undesirable prospect of traveling alone to London for the ceremony. While this is bad enough, Jeffrey (Jeremy Sheffield), the man who left her as they moved closer to marriage, happens to be the groom’s best man. Determined to show everyone — most of all Jeffrey — that her romantic life is as full and thrilling as ever, Kat hires a charming male escort (Dermot Mulroney) as her date.
In a series of interconnected stories, various Los Angeles residents (Jessica Alba, Jessica Biel, Bradley Cooper) wend their way through the highs and lows of love during a single day. As the holiday unfolds, they experience first dates, longtime commitments, youthful crushes and connections to old flames.