Sitting with Oprah at his home in Georgia, the Grammy Award winning entertainer said he felt "lost" after marrying the mother of his two boys.
"Towards the end of the marriage I found myself lost and I just wanted out," said Usher. "I was faithful at heart."
Taking on allegations that he had been "unfaithful" and had been intimate with a bridesmaid, Usher told Oprah they had an "exchange."
"When we were separated, yes I was (unfaithful). We were not divorced," said Usher. "The conversation about the bridesmaid is one that is difficult and complicated. Outside of marriage with her, I did have exchanges with her. We were friends. She was someone who was a part of the children's lives before and it had always been perceived that we had some form of exchange."
While Usher did not come off as being truthful in regards to the bridesmaid, he let it be known that his relationship with Tameka, his ex-wife, remains rocky.
Claiming he requested they delay their ongoing custody case after the death of his stepson, Usher insisted Tameka was the one that wanted to push forward instead of taking time to mourn.
"We don't see eye to eye. The friend that I was to Tameka, I don't know that I ever could be again," said Usher. "She made us enemies in a way I could never understand."
Appearing for the first time in a televised interview, Usher's mom and long-time manager also spoke out on "Oprah's Next Chapter" Sunday.
Claiming she had no regrets about not attending her son's wedding, noting what she saw in Tameka, Jonetta Patton said "I didn't believe she was right for him."
"I couldn't (attend the wedding) because I knew it would be the space that we would be in for the last year. I just couldn't embrace it," said Patton. "I really could not and trust me, I struggled with it."
Detailing a time where Usher came to her and apologized, Patton says he told her "I'm sorry. I should have listened."