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Lindsay Lohan Hosts A 6126 Holiday Collection Fashion Showcase At PURE Nightclub Las Vegas

LOW: A Rocky Relationship With Samantha Ronson (2008)
Besides Lohan’s notable tween romance with pop star Aaron Carter in 2002 (which caused tension between her and fellow teen queen Hilary Duff), Lohan was most famously in a same-sex relationship with DJ Samantha Ronson beginning in 2008 … and a very tumultuous relationship at that. The two were known for blow-up fights and broke up and got back together multiple times. In February 2013, Sam’s mom, Anne Dexter-Jones said she was never comfortable with Lindsay dating her daughter. “I was seriously anxious about Samantha’s safety and wellbeing. I feared tragedy," she told the Daily Mail. "It got to a point that I wasn't sleeping very well." Dexter-Jones pointed to an incident at a hotel party in Dubai in 2008, when Lindsay began rolling around on the carpet and screaming "like a child." "It seemed she was upset that people, including Samantha, were not paying her enough attention," she explained. "To my mind, it was classic psychotic behavior."

Lindsay Lohan Is 27: Relive Her 27 Highest Highs and Lowest Lows

LiLo turned her 27 on July 2, 2013. Take a look back at some of the best and worst moments from the actress's life so far.