Culkin has previously dated actresses Mila Kunis and Jordan Lane Price.
The former child actor looked fit and clean cut both while out on the town.
(Photo by Ryan Miller/Getty Images)LOS ANGELES - MARCH 18: Actor Macaulay Culkin attends a signing for his new book 'Junior' at Barnes & Noble Booksellers at The Grove on March 18, 2006 in Los Angeles, California.
(Photo by David Livingston/Getty Images)Macaulay Culkin and girlfriend Mila Kunis during Joins Forces with Hollywood Stars to Launch Celebrity Auction to Benefit Hurricane Victims - Inside at Empire Ballroom in Las Vegas, Nevada, United States.
(Photo by Dimitrios Kambouris/Wire Image)WILL & GRACE -- 'May Divorce Be with You' Episode 22 -- Pictured: (l-r) Eric Mc Cormack as Will Truman, Macaulay Culkin as Jason 'J.
Song rocked black leather shorts and a loose top with a gray sweater and heels.(Photo by Ethan Miller/Getty Images)Macaulay Culkin during MTV's 'TRL' at Skywalker Ranch for 'Star Wars III: Revenge of the Sith' Screening at Skywalker Ranch in Nicosia, California, United States.***Exclusive*** (Photo by Jeff Kravitz/Film Magic, Inc)BEVERLY HILLS, CA - MAY 13: Actors Macaulay Culkin (L), Seth Green and Wilmer Valderrama pose at the after-party for United Artists' 'Saved' at the Beverly Hills Community Sports Center on May 13, 2004 in Beverly Hills, California.Before Mila Kunis found her happily-ever-after with husband Ashton Kutcher, she had a long-term relationship with Macaulay Culkin.During an appearance on The Howard Stern Show on Tuesday, the 32-year-old actress reflected on her time with the former child star and the “abnormal” fandom that surrounded him.
(Photo by Chris Polk/Film Magic)LAS VEGAS - OCTOBER 15: Actor Macaulay Culkin arrives at the launch of the 'u Bid for Hurricane Relief' charity auction and benefit at the Empire Ballroom October 15, 2005 in Las Vegas, Nevada.