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90s-2000s Romantic Comedies

Romantic favorites from a late GenX-er

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You've Got Mail

1998

Book superstore magnate, Joe Fox and independent book shop owner, Kathleen Kelly fall in love in the anonymity of the Internet—both blissfully unaware that he's trying to put her out of business.

Runaway Bride

1999

Having already left three grooms at the altar, Maggie Carpenter is branded "the runaway bride" by jaded New York journalist Ike Graham. But, after his facts are called into question, Ike races to Maggie's hometown to save his reputation and report on her upcoming fourth trip down the aisle – during which he's convinced she'll run again. Though he's there on a muckraking mission, Ike can't help but fall for this breathtaking heartbreaker.

Only You

1994

Two childhood paranormal incidents have convinced schoolteacher Faith Corvatch that her true love is a guy named "Damon Bradley," but she has yet to meet him. Preparing to marry podiatrist Dwayne in 10 days, Faith receives a phone call from Dwayne's old classmate named Damon Bradley who is on his way to Venice. Faith tries to catch him at the airport but just misses him so she impulsively decides to fly to Venice hoping to finally encounter the man of her dreams; accompanying her on the trip is her sister-in-law and childhood best friend, Kate, who has just left her husband, Faith's brother Larry.

Untamed Heart

1993

Caroline, a young waitress who seems to have bad taste in men, is on her way home one night when thugs attempt to rape her. Adam, the mysterious busboy who works at the same diner, helps fight off the assailants, and she begins a relationship with him -- but not all their fellow Minnesotans are happy for them. Meanwhile, the couple face their own difficulties when Caroline finds about Adam's past, including his unique health condition.

Someone Like You...

2001

Jane Goodale has everything going for her. She's a producer on a popular daytime talk show, and is in a hot romance with the show's dashing executive producer Ray. But when the relationship goes terribly awry, Jane begins an extensive study of the male animal, including her womanizing roommate Eddie. Jane puts her studies and romantic misadventure to use as a pseudonymous sex columnist -- and becomes a sensation.

Notting Hill

1999

William Thacker is a London bookstore owner whose humdrum existence is thrown into romantic turmoil when famous American actress Anna Scott appears in his shop. A chance encounter over spilled orange juice leads to a kiss that blossoms into a full-blown affair. As the average bloke and glamorous movie star draw closer and closer together, they struggle to reconcile their radically different lifestyles in the name of love.

While You Were Sleeping

1995

A transit worker pulls commuter Peter off railway tracks after he's mugged, but—while he's in a coma—his family mistakenly thinks she's Peter's fiancée, and she doesn't correct them. Things get more complicated when she falls for his brother, who's not quite sure that she's who she claims to be.

Sleepless in Seattle

1993

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.

Hope Floats

1998

Birdee Pruitt has been humiliated on live television by her best friend, Connie, who's been sleeping with Birdee's husband, Bill. Birdee tries starting over with her daughter, Bernice, by returning to her small Texas hometown, but she's faced with petty old acquaintances who are thrilled to see Birdee unhappy -- except for her friend Justin. As he helps Birdee get back on her feet, love begins to blossom.

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