At 35, Tripp has an interesting job, a hip car, a passion for sailing, an active dating life, and a great house - trouble is, he still lives with his parents, Al and Sue, who are not happy about it. Al and Sue are fascinated when friends whose adult son has recently moved away from home reveal they hired an expert to help. In desperation to push Tripp out of the nest once and for all, Al and Sue hatch a plan to hire Paula, an "interventionist," who has a formula in these cases.
When perpetually single, aging music industry exec Harry Sanborn, and his latest trophy girlfriend, Marin, arrive at her mother's beach house in the Hamptons, they find that her mother, playwright Erica Barry, also plans to stay for the weekend. Erica is scandalized by the relationship and Harry's sexist ways. But when Harry has a heart attack while there, and the doctor prescribes bedrest, his only option is to stay at the Barry home. Left in the care of Erica and his doctor, a love triangle starts to take shape.
Retired and widowed Chinese master chef Chu lives in modern day Taipei, with his three attractive daughters, all of whom are unattached. Soon, each daughter encounters a new man in their lives. When these new relationships blossom, stereotypes are broken and the living situation within the family changes.
Blonde, bouncy Buffy is your typical high school cheerleader. But all that changes when a strange man informs her she's been chosen by fate to kill vampires.
After taking his dying father's advice, Hal dates only the embodiments of female physical perfection. But that all changes after Hal has an unexpected run-in with self-help guru Tony Robbins. Intrigued by Hal's shallowness, Robbins hypnotizes him into seeing the beauty that exists even in the least physically appealing women. Hal soon falls for Rosemary, but he doesn't realize that his gorgeous girlfriend is actually a 300-pound-not-so-hottie.
As she reaches her mid-thirties and quits her lucrative job, singleton Olivia finds herself unsure about her future and her relationships with her successful and wealthy friends. She begins to envy the security of her richer friends and, although their lives may seem easier, Olivia's friends have their problems too: screenwriters Christine and Patrick are unable to collaborate on their latest project, Jane and Aaron have lost the romance in their relationship, and Franny and Matt have difficulties handling the demands of parenthood.
Despite an unrivaled talent for communicating, Jake has trouble talking to women. When an impossible situation presents itself, Jake ignores the signs and goes on a wild goose-chase to pursue his quest for love. When his plan is foiled, a new best friend helps him finally express himself successfully to a woman – without uttering a single word.
Myles and Brody are best friends with two very different ways of finding love. Displeased with their current love lives, they make a pact to be together if neither finds love in ten year’s time. Now two months shy of their deadline, both friends set off to do whatever it takes to avoid ending up as each other’s last resort.
Stuck dating guys she doesn't like and working at her dead-end job, Hanh finally finds the courage to pursue her dreams.
Dating coach Alex 'Hitch' Hitchens mentors a bumbling client, Albert, who hopes to win the heart of the glamorous Allegra Cole. While Albert makes progress, Hitch faces his own romantic setbacks when proven techniques fail to work on Sara Melas, a tabloid reporter digging for dirt on Allegra Cole's love life. When Sara discovers Hitch's connection to Albert – now Allegra's boyfriend – it threatens to destroy both relationships.
Lovestruck Dustin is dating Alexis, his ideal girlfriend, but when she dumps him for coming on too strong, Dustin takes drastic measures to win her back. He asks his best friend Tank to take her on the worst rebound date imaginable - his side job - so that she will come running back to him, and Tank reluctantly agrees. However, Alexis is more than a match for Tank's shock tactics and he begins to really fall for her, leaving him torn between loyalty to Dustin and his growing attraction toward Alexis.
Fresh out of a long term, serious breakup, Lane Woods chooses to work through (read as: distract himself from) his feelings by making a documentary about his attempts to get back out there and find a new love. With the help of his younger brother, Colin, Lane films himself as he goes on countless dates, hoping to catch those first sparks of love on film, instead he ends up documenting something much closer to reality.
Caroline is forced to leave her unfaithful boyfriend, and the only place she can crash is with her sister Sarah, with whom she does not get along. Sarah graciously offers Caroline a tiny room in her apartment and decides to help her find Mr. Right. Caroline isn't sure she's cut out for the dating game, but Sarah assures her there's nothing to it. Caroline is sent on a series of grueling and comic dates with everything from nimble pickup artists, to adventure sports freaks and a karaokesinging stockbroker. But in the end what the two sisters really find is themselves.
Whatever Works explores the relationship between a crotchety misanthrope, Boris and a naïve, impressionable young runaway from the south, Melody. When Melody's uptight parents arrive in New York to rescue her, they are quickly drawn into wildly unexpected romantic entanglements. Everyone discovers that finding love is just a combination of lucky chance and appreciating the value of "whatever works."
A Chinese-American lesbian and her traditionalist mother are reluctant to go public with secret loves that clash against cultural expectations.
Perpetually single Frankie decides to give up on men in favor of going all-in as a “dog mom" to her adopted dog, Tucker. But sparks fly when Frankie meets Jack, the veterinarian who rescues her dog from near death. They seem destined to be together, but there's one problem: Jack is already engaged.
When an exclusive clique of teenage socialites accidentally murder their best friend on the morning of her birthday, the three girls responsible conspire to hide the truth.
A Jewish man discovers his boyfriend of 10 years has been cheating on him, and decides to embark on a dating spree.
A short centered on the dating adventures of Fran, a 30-year-old New Yorker.
After being dumped by his model girlfriend, aspiring writer Quincy Watson quits his job and is inspired to pen the ultimate how-to book on breaking up. When it becomes a smash bestseller, he starts giving his player cousin, Evan, choice tips on how to win the battle of the sexes. But when Evan's beautiful girlfriend Nikki gets wind of the plan, it's these players that end up getting played.