So deep was their relationship that Timi declined an offer to move to Lagos with his parents, opting to stay back in Port-harcourt with them.

Around that same period, Timi won a local talent hunt contest G.E FACTO, which held in Port Harcourt.

In 2006, Dakolo auditioned for reality show Idols West Africa in Calabar, Cross River State of Nigeria.

After winning Idol West Africa in 2007, on January 1, 2008, New Year's Day, Timi Dakolo was shot at the lobby of the Presidential Hotel in Port Harcourt.

The attack was a random act of violence by a faction of Niger Delta militants and did not target Timi.

Although a hotel security guard was murdered in the attack, Timi escaped with a flesh wound, was rushed to the hospital, treated and discharged on the same day.