Traylor Howard in 1998
Ryan Reynolds’s first big break in the entertainment business came with the 2000 premiere of the TV comedy series Two Guys, a Girl, and a Pizza Place. On the set, he met Traylor Howard for the first time. Their relationship lasted for eight months, but then it ended.
At the time that they were dating, Traylor was ten years older than him. Even a seasoned guy like Reynolds might find it hard to date an older woman, so be ready. Despite everything, the two stayed together for more than a year before they finally decided to break up.