Let me just say...I *HATE* being put in awkward situations...especially when the other person involved is someone I am going to see occasionally. It's not so bad when your probably never going to see the person again, as is the case with awkward situation #1:
I had one random guy walk up to me (at work mind you) and tell me that I look good, it was a little awkward, but not so bad. I was flattered, but if you know me at all, you know it was a bit awkward.
Situation #2 happened today when a guy that I know, that is old enough to be my father...asked if I wanted to go to the movies with him sometime....uhhh...uhh...yep that basically what I said...(that and I don't know...). WHY CANT I JUST SAY NO!!! Umm, or better yet, "Thank You, I'm flattered, but your not my type." Now this is going to make things very awkward anytime I see him.
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