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The orgiastic clusterfuck that is Oscars Week in L.A. can produce just about any variety of celebrity composite, and so one is hardly compelled to raise an eyebrow at sightings involving Orlando Bloom pouring hot fudge from a gravy terrine down Penelope Cruz's cleavage, with an incapacitated Courtney Love lying on the floor directly below, hungrily collecting the drippings. But something about this PrivacyWatch sighting of Real Time host and tireless cokewhores' rights advocate Bill Maher cozying up with Saks' Fifth-Most-Wanted Winona Ryder struck as instantly noteworthy:

Tower Bar, Tuesday night, February 27th. I'm minding my own business, drinking at the bar when who should be ushered past me and into a discreet alcove booth but Bill Maher and Winona Ryder. It looked very "date not business." She sat next to him on the couch, rather than across, learned in, giggled a lot, held his arm while they talked and ate.

At first blush, I was like, "Wow, he's kind of old for her." But a little IMDB work reminded me that she's getting to be "a woman of a certain age" at 35 and he's 50 or 51. Not really that out of place. She's not the Winona of Heathers or Johnny Depp any more. That said, he's the king of porno stars and the Playboy Mansion. All I can think they have in common is leftish politics and a Jewish heritage*. I wish I had been close enough to hear what they were talking about...

Assuming the two aren't simply close, touchy-feely friends, we were initially also taken aback at Maher's unlikely choice of companionship. (Noni? When has she ever promised anyone the "ride of your life" in the back of an L.A. Weekly?) Our operative does make some compelling points as to why the two may have found each other, however: Until now, Maher's definition of commitment involved that time he spent two consecutive weekends at the Playboy mansion with friendscorts Bambee and Cinnamin on his arms; at age 51, perhaps he's finally looking for something more substantial. Ryder, meanwhile, has long since tired of the vicious, pretty-boy-actor dating scene, and was instantly intrigued while combing the JDate profiles of the bachelor with handle "Boys2Mensch," who listed his occupation as "Host of own comedic political roundtable series on HBO."

*Maher's mother is Jewish.