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After losing her boyfriend and her job right before Valentine's Day, Olivia is introduced to George who takes her on a cross country road trip that has them reevaluating their priorities.

Dedicated environmental lawyer Lucy Kelson goes to work for billionaire George Wade as part of a deal to preserve a community center. Indecisive and weak-willed George grows dependent on Lucy's guidance on everything from legal matters to clothing. Exasperated, Lucy gives notice and picks Harvard graduate June Carter as her replacement. As Lucy's time at the firm nears an end, she grows jealous of June and has second thoughts about leaving George.

On the first day at his new school, Cameron instantly falls for Bianca, the gorgeous girl of his dreams. The only problem is that Bianca is forbidden to date until her ill-tempered, completely un-dateable older sister Kat goes out, too. In an attempt to solve his problem, Cameron singles out the only guy who could possibly be a match for Kat: a mysterious bad boy with a nasty reputation of his own.

Two musicians witness a mob hit and struggle to find a way out of the city before they are found by the gangsters. Their only opportunity is to join an all-girl band as they leave on a tour. To make their getaway they must first disguise themselves as women, then keep their identities secret and deal with the problems this brings - such as an attractive bandmate and a very determined suitor.

An epic love story centered around an older man who reads aloud to a woman with Alzheimer's. From a faded notebook, the old man's words bring to life the story about a couple who is separated by World War II, and is then passionately reunited, seven years later, after they have taken different paths.

When the popular, restless Landon Carter is forced to participate in the school drama production, he falls in love with Jamie Sullivan, the daughter of the town's minister. Jamie has a "to-do" list for her life, as well as a very big secret she must keep from Landon.

Eight London couples try to deal with their relationships in different ways. Their tryst with love makes them discover how complicated relationships can be.

After the death of his mother, a young boy calls a radio station in an attempt to set his father up on a date. Talking about his father’s loneliness soon leads to a meeting with a young female journalist, who has flown to Seattle to write a story about the boy and his father.

Nelson is a man devoted to his advertising career in San Francisco. One day, while taking a driving test at the DMV, he meets Sara. She is very different from the other women in his life. Nelson causes her to miss out on taking the test and later that day she tracks him down. One thing leads to another and Nelson ends up living with her through a November that will change his life forever.

Sometimes we meet someone and feel an instant connection like we have known them for ages. It may seem like we were destined to be together, but sometimes nature has other plans. Even when everything seems perfect, there can be imperfections in the three unusual love stories where the characters eventually find their true love.

In the special, Yodonna is given an opportunity to revive as a human on the condition she learn about the emotion of love on Valentine's Day.