Charlie Sheen's 'Date' Mugs with Denise Richards

10/28/2010 8:00 AM PDT by TMZ Staff   Under the category ... be careful who you pose for pictures with ... TMZ has obtained a now-awkward photo of Denise Richards mugging for the camera with Capri Anderson, just hours before The Plaza Hotel incident.

The photo was taken at Daniel restaurant in NYC, where Charlie Sheen, three other guys and five women, including Anderson, went to dinner at 8:00 PM Monday.  Denise was also invited to dinner, showed up and we're told Anderson made a beeline for her, saying she was a big fan and wanted a pic with her.  We're told Denise, who had no idea who the woman was, obliged.

But sources tell us Denise quickly figured it out and became so uncomfortable she left during appetizers.

And you know the rest of the story ... after an alcohol-fueled dinner, Charlie and Anderson, aka Christina Walsh, ended up in his hotel room.

Tags: Denise Richards, Capri Anderson, Charlie Sheen, You Might Want to Rethink

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