Usher Details His ‘Most Difficult’ Life Lesson: ‘The Hardest Thing That I’ve Ever Had To Do Was Be Single’

Usher is getting candid while reflecting on his upbringing, romantic relationships, and life lessons.

RELATED: Chilli Reflects On Past Relationship With Usher & Difficulty They Shared Moving On

Usher Reflects On The “Hardest Thing” He’s Ever “Had To Do”

“The King of R&B” sat down for an exclusive interview with VIBE and opened up about his Vegas residency and decades-long career. During the conversation, the 44-year-old transparently reflected on the “most difficult” lesson he’s learned over the years.

“I think the hardest thing that I’ve ever had to do was be single,” the singer explained before pondering in silence.

Continuing the conversation, Usher added that he doesn’t like “being alone” and began to reflect on his upbringing.

“The idea of creating a life with someone is what I would like to do, maybe because I didn’t have or didn’t see that. And I get to remedy that idea by having an incredible partnership. I can then have the thing that I ultimately wanted to see.”

The Singer Talks “Healing” & What Helped Him To “Be Able To” Be By Himself

As the conversation continued, the singer explained that “healing took a lot,” and “looking back,” he believes he was suffering from “not necessarily having the kind of love” that he “wanted as a kid.”

“Maybe I was suffering a lot from — just maybe not necessarily having the kind of love that I would’ve wanted as a kid. And wanting to figure out what that was all about. I didn’t have that relationship that I would’ve wanted to have with my father. And that the relationship that I had with my mother was slowly beginning to be under pressure. Because one, we were working together. Two, we had our differences. Three, I was getting older, but I think it was just life lessons…”

Usher then shared the resource that ultimately helped him.

“The therapy really did help me be able to be by myself.”

Usher’s Superstar Ex, Chilli, Recently Reflected On Their Relationship

As The Shade Room previously reported, Usher isn’t the only one looking back on earlier days. In June, the singer’s ex, Rozanda “Chill” Thomas, explained that it was for them to move from one another after their brief relationship in the early 2000s.

“I love hard. I was like, ‘God, why can’t I get over this?’ He couldn’t either.”

At the time, Chilli explained that she would prevent herself from participating in the dating pool due to her ongoing ties to the “OMG” singer.

“I even stopped dating. Because before that I thought if I met the right guy during that time that I wasn’t over [Usher] it wouldn’t work. I would never want to straddle the fence.”

Fortunately, things worked out for both parties. Chilli is now dating actor Mathew Lawrence, and Usher is going strong with his partner Jennifer Goicoechea.

Additionally, the couple share two children, a son, and a daughter, while Usher is also the father to two children from his prior marriage to Tameka Foster.

Roomies, what do you think of Usher’s sentiments and transparency? If you want to hear more from the star, check out his recent ‘Stepping Into The Shade Room’ episode below!