While the rumors of their relationship were never confirmed, the chemistry between the two actors on the set of “National Lampoon” was undeniable. The fact that their characters were so compatible in the movie definitely made many curious about the nature of their relationship.
Their shared appearance on “TRL” also fueled rumors at the time. Tara Reid was one of the most prominent comedy stars at the time, thanks to her role in the “American Pie” series.
Rachael Leigh Cook - Today
Something good came out of Rachael and Ryan's breakup, that's for sure! The actress started dating fellow actor David Gillies after she and Ryan split in 2001. The two married in 2004 and had two children together, a daughter, born in 2013, and a son born in 2015.
Sadly, the couple announced they were splitting in mid-2019. They had decided to go their separate ways after nearly 15 years of marriage. It seems like the actress is currently single; perhaps she focuses her energy on a major comeback in her career?
Tara Reid - 2002
In 2002, Ryan played Van Wilder, the lead role in the movie "National Lampoon’s Van Wilder." Tara Reid portrayed his love interest, and their chemistry both and offset was excellent.
Everyone was surprised when they didn't become a couple, especially since they were both single at the time. Though, we have heard through the grapevine that they had a short affair behind the scenes. What do you think?
Tara Reid - Today
Tara has had quite an eventful love life. In 2010, the actress got engaged to Michael Axtmann, but the two decided to go their separate ways just 3 months later. She then dated Michael Lillelund, declaring she married him in August 2011. Oddly, he has denied this claim.
That same month, she said she married Zachary Kehayov but later explained that it was not a legal marriage. From 2013 to 2014, she dated musician Erez Eisen. Reid has learned a thing or two about keeping her love life private and has since seemed to have kept this part of her life off the public radar.
Alyssa Milano - 2002
Ryan was a big rom-com actor in the early 2000s. In the 2002 film "Buying the Cow," he was cast as the stereotypical womanizer opposite the "Charmed" star, Alyssa Milano. If you've watched the film, it's easy to see that these two connect, which is probably why gossip arose on set.
Though they made a cute movie couple, the actors claimed that nothing ever happened between them. Though we'll never know for sure, it's nice to imagine what could have been if the two had been official.