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After writing a soon-to-be bestselling novel, writer and committed bachelor Harper Stewart (Taye Diggs) attempts to hide the fact that his saucy new book is loosely based on the lives and loves of his tight-knit group of friends. Harper is set to be the best man at his friend Lance's (Morris Chestnut) wedding, and all his friends will be in attendance. When an advance copy of the book makes its way into the hands of his ex-flame, Jordan Armstrong (Nia Long), Harper attempts to keep it under wraps.
Two urban African-Americans, Darius (Larenz Tate), an aspiring writer, and Nina (Nia Long), an aspiring photographer, share an instant connection after a chance meeting at a Chicago club. The two bond over music, photography and poetry, and eventually begin a torrid romance. However, when Nina decides to move to New York and mend her relationship with her ex-fiancé, Marvin (Khalil Kain), it leaves Darius heartbroken, and the couple's future in jeopardy.
Kenny plans to propose to Angelique, but her recent actions have him second guessing; when Mabel is approached by the local newspaper for a front-page feature, things go awry when they dig into her past.
Jay looks for a replacement to run Mable's Tables and discovers his ex-convict brother-in-law is moving in at home; Kenny is dismayed by Angelique's antique doll collection.
Jay undergoes dental surgery and milks his recovery for longer than necessary; meanwhile, Mable's Tables' new manager Trish Devoe has a new plan to grow business for the restaurant.
An old friend of Jay's resurfaces while, Percy struggles in revealing a secret he has kept from his parents.
Kenny's famous favorite aunt visits with her new boyfriend; meanwhile, Wade lists his apartment on a vacation rental property site.
Cheryl starts an in-home salon; at Mable's Tables, Trish, desperate for a chef, teaches Karen how to cook.