Usher fears he has been too "experimental" in his romantic relationships.
The singer is currently embroiled in a bitter custody battle with his ex-wife Tameka Foster, who this week claimed he cheated on her with a woman who had been a bridesmaid at their wedding.
Usher has spoken philosophically about romance, claiming his protégé Justin Bieber is actually better at them than he is.
"Well, check it out, it the area of relationships, he's actually done a lot better than I did," Usher told Q magazine.
"He doesn't have as many issues. He knows what he wants. What were my issues? Well maybe not locking into one relationship! I was a little bit more… experimental. I've had many women. And I understand how to deal with a lot of different ones… But it is complicated when your reality is a fantasy. Fame is the modern double-edged sword."
The 33-year-old thinks many men make the mistake of thinking all women are the same. He understands that isn't the case and has also realised what they find sexy in a man.
"There's a lot of them," he laughed, when asked what he has learnt about females.
"And they are all different. So, puh-lease, in no way, shape, form or fashion should you ever put them in the same box or category. But I've learned what women like. Confidence. And I've learned there is a softness that only a woman can possess. And you begin to see it when they have something, like a child, to love."
Usher also discussed his lengthy music career. He has sold over 68 million records around the world and has no doubt about why he has enjoyed such success.
"[I'm] a sponge, the more I absorb, the more I am able to articulate my vision, as artists do, like Picasso. I'm an artist in that light. I went from being an artist to an artiste," he said.