Simon is a man known for his dating history and, specifically, bad dating history. His first known relationship with a woman was in 2005 when he began dating Meg Mathews, the ex-wife of Oasis guitarist Noel Gallagher. Their love tales used to make headlines on the top media house’s websites and newspapers. Jordan liked to spend money on his partner, so he gave Meg a Porsche for £100,000 for Christmas in January 2006, complete with a custom license plate.
However, right after that, the relationship began to crumble apart, and just two months after that, they announced their separation due to personal reasons. Jordan stated that Meg ended the relationship, and the couple decided to part ways after that.
He was a victim of harassment by a woman named Tara Stout in October 2006. After that, he dated another lady named Suzi Walker for a while, and they even had a child named Cameron in January 2008. He got separated from Suzi and later mentioned that the birth of Cameron was unintentional and their relationship wasn’t going anywhere forward, so they had to split.
After that, he went to emotional and financial breakdown, losing his ownership of Crytal palace and major stocks in different companies he had invested in. However, in July 2019, Daily Mail reported he was spotted with an English businesswoman and media personality, Michelle Dewberry. Their relationship has been going on smoothly till now, and the couple still has expressed their ideas regarding marriage in the future. They have a son together, born on July 18 2020. With this child, Simon is now a father to two children from two different women.
