When it comes to love, former reality star Jon Gosselin has certainly experienced his share of ups and downs. Jon was married to ex-wife Kate Gosselin, with whom he shares eight children, from 1999 until the pair's divorce in 2009. Though the Gosselins' marriage came to an end amid accusations Jon had ben unfaithful, he continuously denied the claims. Since then, Jon has dated several women before becoming engaged to Stephanie Lebo in 2024. At the time, Jon told The U.S. Sun, "We are really happy and in love. We are very comfortable with each other; it just fits.