The Open Mic Talent Scouts
Everyone is looking for their 15 minutes of fame (or however long they can stretch it), especially people actually performing. So, find a local open mic--comedy, music, whatever--and make a plan!
You and your date will attend the "performance" under the assumed identity of Talent Scouts. Create whatever fake talent agency you want (extra credit if you can come up with some fake business cards--granted, this could be as easy as cutting a 3x5 card into a business card and hand writing something to the effect of "Good Talent Scout"). Another great prop to bring is a pen and pad to take notes (or play a game of Hangman with your date if the performers are that boring).