Lohan reportedly hooked up with the Cruel Intentions star in 2007, shortly after his split from Reese Witherspoon. (Another misspelled name, BTW, as Lohan only had one "L" in his last name, which...fair.)
Per Us Weekly, Lohan "loved the drama" of it all. Per Phillippe in a 2008 interview with Howard Stern addressing the report, the MTV reality star "wanted" him but denied a hookup.
Post List-Life: Phillippe went to the small screen in the wake of LiLo List-gate, starring in ABC's Secrets and Lies before USA Network's Shooter from 2016 to 2018.
As for his love life, he was engaged to law student Paulina Slagte for a few years before calling it quits in 2016. Then, Phillippe rumored to have hooked up with Katy Perry in 2017, but he hilariously denied it by tweeting, "I am not dating Katy Perry. Barely know her. Please stop flying helicopters over my house. She is not here. Thx."
Perry joined in on the fun, responding, "Can you let me out of this basement pls?" She then added, "Hi, @RyanPhillippe, nice to meet you. Sorry about that. Carry on."
Later that year, though, his ex-girlfriend Elsie Hewitt filed a $1 million assault lawsuit against the 44-year-old father of two, with the Play Miss June 2017 alleging he kicked and punched her during a fight over the summer. An "utterly devastated" Phillippe denied the claim, with his rep calling it "utterly false" and an "unjustified attempt to extort money from Phillippe, and to gain publicity for herself and her modeling career."
And in December 2018, Phillippe tweeted a a few non-sequiturs while on vacation, with one calling out an unnamed opportunist ex going on to receive some attention.
"hey. if you're an ex of mine, stop asking people you met through me for free stuff, cuz i don't, n it's a BAD look for you. love ryan. ever bod keep being like, 'your ex callin for free s--t and we don't know her like that. smh," he griped. "frankly, i'm tired of hearing ab it. find ya own.'"