The two, who have been dating for four years, are set to celebrate their engagement and the new year at the Five Star New Year’s event on Watson Island in Miami.Ryan recently gushed about Slagter on Howard Stern’s Sirius XM radio show, saying, "She's awesome.“I’m looking forward to the new challenges and facing them.If I really think about each and every aspect or category in my life, there is something to look forward to and for that I’m really grateful. When people see her they have these judgments because she could be a model, but she's about to graduate Stanford Law.Also what's great about it — as you get older, certain issues become more important to you.After leaving the show, Phillippe moved to Los Angeles, where he appeared in a number of small parts in various television series including Matlock, Due South, the TV miniseries The Secrets of Lake Success, and movies, including the 1995 film Crimson Tide and the 1996 film White Squall.
In the years following, he appeared in the crime drama The Way of the Gun, starred as a famed software engineer in the thriller Antitrust, and co-starred in Robert Altman's Gosford Park, which was nominated for the Oscar for Best Picture.
“I’ve faced every manner of gossip, and I don’t take myself as seriously now,” he says.
“There is a freedom and a release that comes with maturity. We live in a time where being a private person isn’t really an option anymore.” Phillippe, 42, also shares 5-year-old daughter, Kailani, with former girlfriend Alexis Knapp, recently broke off his engagement to law student Paulina Slagter in November after five years together. ” RELATED VIDEO: Reese Witherspoon and Daughter Ava Phillippe Look Like Twins!
In 1999 he starred in Cruel Intentions, a modern retelling of the Choderlos de Laclos novel Les Liaisons Dangereuses, which also starred Phillippe's future wife Reese Witherspoon, as well as his I Know What You Did Last Summer co-star Sarah Michelle Gellar.
It was a success among its intended teenage audience, cementing Phillippe's ability to play characters that require sex appeal.