Sandra Bullock

Sandra Bullock may be one of America’s most beloved sweethearts, but the charming actress has not always had the best experiences in the romance department. The Miss Congeniality actress has had a few relationships in the past, but her marriage to television personality Jesse James is probably the most well-known.

Sandra and Jesse in the early 2000s and married in 2005. They were an unlikely pair, but the couple did spend a few good years before ending their marriage in 2010. The months that followed their separation saw plagues of social issues and a certain degree of controversy. Sandra even canceled press promotions to cope with her situation. However, Sandra was quick to get back on her feet. After spending some time as a single parent to her son, she began dating Bryan Randall in 2015. The two have been together for five years now, and it seems like their relationship is only getting stronger by the day.