The series begins with the viewers meeting J Calvin Frazier and his friends Gordon and his wife Sherri. J works at a boxing company, Gordon works at a law firm and Sheri is a book editor. J has recently discovered that his roommate has moved out and now he has to find a new one. He gets a roommate in the form of Robin, who thinks he's gay. One of Gordon's coworkers, Marcus is dating one of J's old girlfriends. J now has to deal with his new roommate and the feelings he has for his old flame.

While playing the game of Truth Be Told, J discovers that his girlfriend is still a virgin. While Gordon discovers that he wasn't Sherri's first experience. J and Melissa decide to have sex and J experinces some bedroom problems.

J quits his job and tries to get another one. He hangs out at a spa to mingle with important business professionals. He eventually gets a new job when he runs into a female member of the club that has her own company.

J and Gordon fight over ownership of a comic book-that Shari put on Ebay. The comic puts their friendship in jeopardy. The book is worthless since Gordon cut an ad out of the book. The only winner was Marcus, who cashed in on the legal fees.

J enters a bachelor auction to make his new girlfriend jealous. He gets bought by Gordon's Boss daughter who has a fatal attraction to him.

J takes an encounter with a newspaper columnist, who annoyed him and turns it into a chance at getting his own nationally syndicated column.

Against Melissa's wishes, J arranges to meet her parents while they're in town visiting, but quickly discovers why she was so reluctant to introduce him to her germaphobic mother and crazy father. Meanwhile, Gordon and Shari try their hand at writing a children's book, hoping to win a contest that awards the winning author $50,000.

J's brother comes to town with news of his impending marriage to Donna. Donna just happens to have had a fling with J years ago.

J goes to Las Vegas to try to stop his brother's wedding to Donna.

J's girlfriend Melissa returns from abroad in time for Thanksgiving, but their relationship isn't the same after months of separation.

J and Gordon go crazy with their fantasies, as Gordon loves Shari in her new Scully wig. J dates a former Chicago Bulls Cheerleader.

J tries to score points with his boss by watching his log cabin during a blizzard. J brings his friends along and everything goes bad.

J tells a blind date that he'll call her and doesn't, so his karma suddenly go bad. He gets locked out of his apartment, gets an infection on his butt and loses to Gordon in Basketball. Meanwhile Gordon investigates his maid and finds out what she really does.

J, Gordon and Shari get cast as extras in Cameron Russell's new movie. J discovers the other side of his favorite action hero.

J and Marcus battle to see who can get the most attractive date. J gets multiple dates and everything backfires in his face.

J meets an older woman and begins dating her. Unknowing to him, she's Logan's mother and Logan discovers them in bed together. Logan claims that it doesn't bother him, but he has J doing more work. It's not until Logan's mother finds out that J's suffering comes to an end as does thier relationship.

J agrees to watch Melissa's dog, who doesn't like him.

J buys a Mercedes to pretend to be successful and ends up going into poverty to pay the expensive bill off.

J creates his own boy band, the Macho Five. It backfires in his face when the group dumps him and makes Gordon a member.

J tries to match Logan up with the new intern.

J tries to help some of his coworkers with dating by offering them tips. He also discover that Melissa is getting married after he sees her with a wedding wing. He realizes that he loves her and proses to her. Melissa agreeds and reveals that the ring was her girl friend'd ring for her marriage.