Jason "Laying The Groundwork" Sudeikis strikes again. This time, he's sidling up to an unexpected target: Ashley Olsen. According to the New York Daily News, the unpretentious funny guy -- who uses humor to befriend and then score with A-list ladies -- had his "arm around" the wee, typically reserved millionaireness while they "snuggled" in a booth at the Stone Rose Lounge in New York City. It happened at Monday's after-party for the new Brett Rattner movie "Tower Heist," co-starring Eddie Murphy and Matthew Broderick.
Olsen, 25, broke off her engagement to actor Justin Bartha earlier this year; Sudeikis, 36, Hollywood's most improbable and under-the-radar casanova, has previously charmed the likes of Eva Mendes (mission successful), January Jones (mission successful, and the kid is not his son) and Scarlett Johansson (mission unsuccessful, but it wasn't for lack of trying.)
A publicist who represents both Sudeikis and Olsen did not immediately respond to a request for comment on the hookup reports.