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Most embarrassing thing that has happened when you attempted to flirt with someone?

Mine was yesterday, I went to the cafe I always go to before work and this gorgeous gal was there on her laptop. I sat my snapple down and threw out my receipt in the trash can that was in front of her (not paying much attention to her) and as I'm sitting back down I notice her looking back and smiling (at what I thought was me). I smiled in return of the incredibly rare event, and she proceeds to laugh awkwardly and explain she that she was smiling about my snapple something-or-other and I lost interest in what she was saying, somewhat defeated, ha ha. Felt pretty lame.

Any embarrassing experiences from fellow GAGers out there?
Most embarrassing thing that has happened when you attempted to flirt with someone?
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