| Date | Description |
| March 24, 2000 | 25 Finalists are chosen from a nationwide talent search which took place in November of '99 in:Honolulu, Los Angeles, Las Vegas, Dallas, Nashville, Chicago, New York City, and Orlando. The casting will narrow down to 8 finalists, which will then lead to the 5 finalists who will become O-Town. |
| March 31, 2000 | The 8 finalists settle into their new home and schedule in Orlando. |
| April 7, 2000 | When Jacob and Erik write a song together, 2 bandmates show they are serious about music, but the temptations of partying with girls is too hard for them to resist. |
| April 14, 2000 | Ikaika and Paul's girlfriends come to visit, which causes them to examine their devotion to love and their music careers. |
| April 21, 2000 | Cori causes waves for Mike and Ashley, who find romance,br>
during a visit from his girlfriend Shelley. The bands finalists take their vocal training out of the studio. |
| April 28, 2000 | The record contracts being passed out, causes the O-Town finalists to react with mixed feelings. |
| May 26, 2000 | A special 1 hour recap of all the drama, fun, and excitement of how Jacob, Michael, Bryan, Paul, Ashley, Erik, Trevor, and Ikaika have come together in a once-in-a-lifetime opportunity to become the next pop music sensations. |
| June 2, 2000 | The O-Town finalists say goodbye to Paul when he announces his decision to leave the group. |
| June 9, 2000 | The O-Town finalists go to a New Year's Eve party. |
| June 16, 2000 | The finalists are ready to record their first song, "All For Love", but problems happen when Ikaika returns from Hawaii. As the countdown to the final 5, tensions mount as the finalists confront Ikaika about his lack of commitment. |
| June 23, 2000 | Lou steps in as tension builds between Jacob and Ikaika. Also, the moment arrives as tears and and laughter are shared when Lou announces the 5 O-Town members. |
| June 30, 2000 | Overcome with emotion, the band bid farewell to the 2 finalists who didn't make it. Meanwhile, Ashley and Shelley struggle with the stress of a long distance relationship. |
| July 7, 2000 | The 5 finalists settle into their new roles as O-Town. Makeovers and photo sessions become part of everyday life. |
| July 14, 2000 | O-Town begins to crumble when the band's vocal and dance trainers begin to point out problems with their performance. The guys also are gearing up for their first public appearance. |
| July 21, 2000 | After a nerve-racking dress rehearsal in front of a top MTV executive, the pressure from their managers and coaches cause the band members to evaluate themselves as performers. |
| July 28, 2000 | The guys get a pep talk before their 1st real performance in front of record executives at The House Of Blues. O-Town delivers a strong 1st performance, which creates interest from the record executive and may ultimately lead to a record deal. |
| August 4, 2000 | OTown arrives in LA for a press tour, which will involve phone and radio interviews, along with a photo shoot. Ikaika is still having difficulty adapting to this environment and realizes that he must make a decision soon, and after not showing up for an important photo shoot, Ikaika makes an announcement about quitting the band. |
| August 11, 2000 | Even after the guys beg Ikaika to stay in LA 1 more day to finish the important photo shoot, Ikaika follows the orders of his older brother to return to Hawaii immediately. The remaining 4, try to record "Baby I Would", but realize they need a 5th member. The guys want Dan Miller to be the 5th. |
| August 18, 2000 | Dan Miller arrives in Orlando and witnesses a scolding from vocal coach Mark, on O-Town's lack of commitment to practice. After Mark threatens to quit, Lou has a serious sit-down with the guys and places them on restriction from going out at night until they leave for Germany. |
| August 25, 2000 | As O-Town prepares to leave for Germany, Erik gets in trouble with Lou and his fellow band members, for not taking care of himself when he is sick. |
| September 1, 2000 | The band heads out on it's 1st vacation to Cancun accompanied by Ashley and Dan's girlfriends. Ashley tells Shelli that he wants them to spend time away from each other for awhile so that he can focus on his career while she goes on with her life. |
| September 8, 2000 | The band goes to New York to perform in front of record company executives, and hopefully land a record contract. O-Town heads to Georgia where Dan will participate in his 1st band performance in front of 2000 fans. 3 months later, O-Town arrives in New York to sign a record contract with Clive Davis. |
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