In early 1999, he had an on and off relationship with Jessica Simpson, the pop star.  Both of them got married in 2002. Within three years, they announced that their marriage is not working and got separated. They filed for a divorce in 2005 and got separated legally in 2006. The amount of settlement is not known to the public but, Nick sold his Calabasa mansion for the settlement.

In the same year, he started dating his next girlfriend; Vanessa Minnillo. They announced that they broke up in 2009 and immediately another news about Nick’s engagement with Vanessa roared. They got married in 2011. He is currently living with his wife and his son. Nick also dated Kim Kardashian for a few months in 2007.

The reason of separation from Jessica is said to be a weird bachelor party that Nick attended. The couple seem to deny this rumor. There were a lot of pictures of them shopping and cuddling. But, within a few months, the relationship was called off. They had a lot of fights according to Jessica’s father. However, he said that he did not interpret the fighting as a sign of divorce. In 2005, there were rumors that the pair has hired divorce lawyers and have filed all the papers. Yet, the pair denied about their separation.

The pair also broke up for a few months, just before their engagement. This breakup is the common factor in both his affairs. The Nick- Jessica separation story has two different sides. Jessica’s side talks about his partying and refusal of joining his family even for festivals. On Nick’s side, Jessica just said that she wanted to be separated and she blindsided her husband on a car ride back from LA. One of the sources also indicated that Nick loved Jessica, a lot and did not want to get divorced from her. However, she did not think that the relationship could work anymore.

The most interesting reason for the separation was that Nick found Jessica cheating with her secret boyfriend. There were also stories about her dad being the reason for the split. Both the parties denied the rumors. They sold all the furniture they used and also the house they were in. She got the Beverly Hills estate as she wanted to be in that house for the rest of her life.

Later; in an interview Nick quoted gay jokes about Jessica’s father. Jessica was angry because of this incident. Nick said that he has not spoken to her for about 7 years. Jessica reported that Nick does not have a right to speak about her family anymore. When asked whether her father was the reason for the separation he said that his father-in-law did a few things and he did not know the purpose of those. But, Jessica is a grown woman and she knew what would suit her well. Nick did not want to blame her father for the separation.