Chilli (of pop/RandB group TLC) brings in love expert Tionna Smalls to help her find the one thing she wants most...a man. The challenge is made difficult by Chilli's checklist of things she expects in her man and by champion boxer Floyd Mayweather who wants to date Chilli as well.
Chilli throws the first pitch at an Atlanta Braves baseball game and Tionna uses the opportunity to recruit eligible men from the crowd. Floyd Mayweather takes Chilli roller skating and pushes for a deeper relationship.
Chilli decides to put everything on the line with Floyd Mayweather to see if he can be the one. TLC plays a benefit concert in Las Vegas with Justin Timberlake, Taylor Swift and Snoop Dogg.
Tionna sets Chilli up with a variety of guys from a medal winning Olympic athlete to an Iraq war veteran. As Chilli continues to reject the guys, Tionna's frustration grows until tempers flare and Chilli and Tionna's relationship is put in jeopardy.
Tionna pushes Chilli to see a therapist where Chilli breaks down and reveals a personal, shocking story that helps to explain the existence of her checklist and high standards for men.
Tionna ask the help of T-Boz and Chilli's close friends in finding more qualified guys for Chilli to date. A sexy calendar model gets all the girls attention, and makes the cut for a date with Chilli.
Chilli starts to get serious with two guys while frustration mounts between Tionna and Chilli resulting in a confrontation.
As Tionna prepares to return to New York, she pushes Chilli to get more intimate, and go on overnight dates with two guys she likes. Chilli faces a difficult choice.
Chilli is jolted by a visit to the doctor. Floyd Mayweather takes Chilli on a date, and Tionna has a surprise for both of them.
As Chilli confronts Floyd Mayweather about their future, Tionna tempts Chilli with a sexy Indy race car driver.
In Miami, two men have Chilli's heart racing. A psychic predicts Chilli's romantic future.
When Tionna discovers a shocking revelation about someone Chilli is dating, Chilli faces a dilemma on what to do next.
Chilli gets grilled on the Steve Harvey radio show. A visit to New York City leads to a romantic surprise.
When Chilli learns about a hot prospect's past sex life, issues of trust emerge. Later, a gathering of Chilli's family becomes surprisingly dramatic.
Chilli seeks her therapist's help with a difficult issue. A romantic date in the country takes a surprising turn.
Chilli confronts her father. Chilli brings a date to the Soul Train Awards.