5. Usher and Chili Its hard to find one person who didn’t want this relationship to last. Anyone who is a fan of either one of them knew that that they were perfect for each other; Usher was the young bachelor in love with the older and tamer Chilli. Everyone thought that marriage was on the horizon for them, until rumors of Usher cheating surfaced and the two traveled down the road to Splitsville in 2003. After the split, Usher married (and later divorced) Tameka Foster, and had two children with her, Usher IV and Naviyd.  Chilli is still looking for the love of her life and has since starred in her own reality show “What Chilli Wants” to document her search.