Tara Reid – 2002
In the 2002 production of “Van Wilder” by National Lampoon, Ryan portrayed the lead role of the titular character. His on-screen love interest, represented by Tara Reid, was seated right across from him, and the two of them shared a strong connection. Even though none of them had a spouse at the time, we were all surprised when it turned out that these two would never end up getting married to one another.
Rumours are going around that the two of them may have engaged in a shadowy affair on and off in the past. This contention finds additional backing from the fact that Ryan frequently prefers collaborating with blonde co-stars in film and television projects.45