Dempsey earned celebrity status from his roles in Can’t Buy Me Love and Loverboy (1989) and she was surprised when he walked through the salon door for a haircut.
However, like Sweet Home Alabama (2002) the romcom he stars with Reese Witherspoon, their relationship was complicated by another partner. Dempsey and Jillian were both in relationships and after three years of haircuts and conversation, the pair finally came together.
The couple was married in 1999 at his family’s farmhouse in Maine, an intimate ceremony where Kristen Mason, the bride’s sister and business partner, said, “He saw her and started crying.”
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