10 celebs and their biggest regrets (With Pictures)

2. Usher Marrying Tameka Raymond

Usher went against his family’s wishes when they told him not to marry celebrity stylist, Tameka Raymond. Not only was she much older than him when they began dating, but there was something about Tameka that didn’t sit too well with Usher’s family. Especially his mother, Jonetta Patton. Usher went on to marry Tameka without his mother at the wedding, and a few years later, the singer began seeing what Patton saw in Tameka the entire time. She was crazy! Usher could no longer deal with his wife, so he signed the divorce papers and dumped her. He has since admitted that the mother of his two children is the “best mistake” he has ever made. Presumably because the twosome had kids with one another.