56. Usher and Jenn Goicoechea
American singer-songwriter Usher, 43, has had a few of his romantic relationships in the spotlight. In the early 2000s, he dated TLC member Chilli Thomas, and while he’s never confirmed why the relationship ended, fans suspect he admits to infidelity in his song “Confessions”, which was released shortly after the breakup.
The singer has been married twice, and in 2019 he started dating music executive Jenn Goicoechea. The couple welcomed to the world their first daughter in 2020, and in May 2021, they attended the red carpet together, where it was revealed Goicoechea was pregnant. Their son was born in September 2021.