During a 2008 concert at Carnegie Hall, Jill Scott revealed that she was in a relationship with her drummer, Lil John Roberts, and that they were actually engaged to be married, per Essence. This wasn't her first engagement ring: Scott was previously married to Lyzel Williams, but they filed for divorce in 2007.

Shortly after her on-stage reveal, Scott and Roberts announced that they were expecting a baby. Her pregnancy took Scott by surprise, as she later admitted on Instagram. "I thought I was terminally ill," the singer recalled, explaining that she noticed that she was oversleeping and couldn't stay awake. "I prepared for the worst but Jehovah gave me THE BEST surprise ever." She had previously assumed that she was unable to give birth due to reproductive problems, as Scott revealed to People. "I was married for five years and could never conceive a child. Until now... It's the most amazing thing that's ever happened to me."

The baby, Jett Hamilton, was born on April 20, 2009. Scott and Roberts called off their engagement a couple of months later, but decided to co-parent.

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