In 1994, when Dempsey was 28, he walked into the Delux salon and met his stylist Jillian Fink, who was also the owner.
A 2002 story published in People, recounts their meeting.

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.
“I was shocked,” Fink recalls of that moment. “But at the same time, I was happy because he was so cute.”
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.Continue reading…