After an accidental meeting, two New Yorkers decide to go on a date where they each bring a friend.
Romantic obstacles abound during Kate and Ben's first official date.
As Ben tries to find the perfect birthday present for Kate, his advice to her may ruin her friendship with Connie.
When Kate's younger sister, Julia, makes her first visit to New York, an overprotective Kate seems to forget that Julia is no longer a kid.
Ben is determined to win Connie over by helping her at her nanny job, while Kate tries to change Larry's ways.
Kate uses the building's security cameras to spy on Ben when he's forced to work late nights with his ex-girlfriend.
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