When it's a guy friend flirting with me I'll pretty much always flirt back even if I'm really not that interested, because it's just some harmless fun. But as far as awkward pick-up attempts, two really stand out in my mind.
One was in my health class last year when I got paired up with a guy who I'd never even seen before in my life. Our subject was dating, and literally 2 seconds after introducing myself to him and opening my book, he was like, "So, Mickey, on the topic of dating, what would you say if I asked you on a date?"
Since he caught me off guard I was just like, "Uh, no?" and laughed. I actually felt pretty bad about that one... I didn't mean to be so harsh.
But then the funny story was when I was in the Dominican Republic with my whole family. This absolutely GORGEOUS guy (who was maybe 21 or so, a tad too old for me) comes over to me and smiled and was like, "I just had to tell you, you're the prettiest girl I've seen all day."
My dad then walked over from behind me and said, "Yep, I agree, prettiest high school student that I know!" and turned me away. The look on the guy's face was pretty hilarious, even I had to laugh about it.
I love flirting. It's such a great mood and confidence booster. But I REALLY hate when much older guys say flirty or suggestive things to me. It always makes me so skeeved out.