He got married to Kim Fey in 1999. He has two children from this marriage. In 2008, Fey filed for a separation from her husband stating irreconcilable differences as the reason. In 2013, he started dating Jenny McCarthy and they announced their engagement in 2014. Kim requested for spousal support and the legal support from Donnie. She also sought the full custody of the children and Donnie was given the visitation rights. It was rumored that the main reason for the divorce was his career. He started spending a lot of time on the road, than with his family. It was also said that she did not initiate the separation, but they filed for separation on the same day. Donnie never mentioned about his life with Kim and why he got separated from his former wife.

He talks a lot about his girlfriend. He said that he is bonding well with her son. They got engaged on the next day of her separation from her spouse. Donnie was not her secret boyfriend. After she got separated from her spouse, she spent almost a year, not dating anyone. When she first met Donnie, she thought he was gay. She said that she never gave her number because she thought he should either be gay or married. However, as time passed by, they started to bond well and it took him two weeks to call back after she gave him, her number.

After he got split from his former spouse, he started dating a Canadian model, who was rumored to be Michelle Tonlinson. He started seeing her right after the separation and maintained an intimate relationship with her, for more than two years. It was said that when Michelle told him that she was pregnant with his child, he broke up with her. The sources near to her said that he freaked out when she informed that she was pregnant and told her that things between them are over. It was said that he was already cheating on Kim with a lot of affairs. Though infidelity was not the reason cited for the separation, his womanizing actions are well known to people around him. She gave birth to his biological child and never sued him for child support.

Though Jenny and Donnie are having a smooth relationship, Donnie’s family considers Jenny as a gold digger. Jenny and Donnie are not known to have any secret relationships, problems or other jitters that might lead to the break up of the engagement, in the near future. Though Donnie’s family is totally against, he is very sure that he wants to be with Jenny. Jenny said that she thought she would never get married again, but, at last, found true love. She was previously married to John Asher and has a 11 year old autistic son with him. They got separated in 2014, a day before her engagement with Donnie.