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With Valentine’s Day approaching, Eve Lovett (Joely Fisher), a workaholic TV talk show host with a string of failed relationships, is worried she will never find true love. But when a mysterious stranger named Vernon Gart (Jamie Kennedy) shows up on the set claiming to work for Cupid, Inc., Eve has no idea her love life is about to get an arrow right through the heart.
When Berke Landers, a popular high school basketball star, gets dumped by his life-long girlfriend, Allison, he soon begins to lose it. But with the help of his best friend Felix’s sister Kelly, he follows his ex into the school’s spring musical. Thus ensues a love triangle loosely based upon Shakespeare’s “A Midsummer Night’s Dream”, where Berke is only to find himself getting over Allison and beginning to fall for Kelly.
Posing as a hangman, Mace Bishop arrives in town with the intention of freeing a gang of outlaws, including his brother, from the gallows. Mace urges his younger brother to give up crime. The sheriff chases the brothers to Mexico. They join forces, however, against a group of Mexican bandits.
Hopeless romantic Matt (Brandon W. Jones) decides it’s time to pop the big question to his girlfriend, Alexis (Cassi Thomson). Before the big evening he practices his proposal on his best friend, Liz (Christa B. Allen). Matt believes if he follows the rules of all of his favorite romantic comedies he’s guaranteed a “Yes!” To Matt’s dismay, Alexis gently rejects him stating he’s only interested in the idea of being in love and not a real relationship. After this unexpected disaster, Matt binge watches one rom-com after another and comes up with plan to win Alexis back. Though Liz thinks Matt’s plan is absurd she agrees to be his wingman. The operation to rekindle his relationship appears to be working only for Matt to face the reality that he and Alexis may have grown apart and his heart belongs elsewhere.
Jake and Kyle are two boys who grew up together in rural Arizona. They are best friends, and they begin to take their relationship to the next level when Jake’s father moves him and his family away to California. Jake and Kyle can never forget their strong emotional bond, and Jake, overworked and unattached, goes back to his hometown for the first time in 15 years to see Kyle and renew their special friendship.
Duke Fergus falls for Ann ‘Flaxen’ Tarry in the Barbary Coast in turn-of-the-century San Francisco. He loses money to crooked gambler Boss Tito Morell, goes home, learns to gamble, and returns. After he makes a fortune, he opens his own place with Flaxen as the entertainer; but the 1906 quake destroys his place.
‘Tis the Season for Evelyn Wright…literally, she is a party planner in NYC. At the last minute Eve finds out that one of her agency’s top clients is throwing a HUGE Christmas event, in LA, on Christmas Eve! Eve must decide whether to take on the event or risk her career to go on a romantic vacation with her boyfriend Darren. Unbeknownst to Eve, her future all depends on whether or not she makes a plane. We see it both ways, in parallel.