Firstly I should point out that my whole life is probably best described as one big awkward moment but here are the edited highlights:

• When people accidentally hit/brush/nudge my breasts.
• Went to see one of my close friends perform in the Vagina Monologues [v good, I recommend it] and she did this little speech about some horrific forms of genital mutilation that take place around the world. After she was done I applauded her, as a friend should, but I was the only person in the whole room that did. Apparently you don't clap for bad things, no matter how well it was spoken. The worst thing is, I immediately felt so awkward I had to laugh so then it looked like I was basically cheering on genital mutilation. Whoop whoop.
• Whenever a left-handed person is writing I just feel really awkward, I can't explain it.
• At work in the pharmacy a young woman came in and planted both hands down on the counter and said, "right; my brother is retarded." I laughed because it sounded like she was making a joke. As it turns out, her brother had Downs Syndrome and she wanted to see about getting help making up his pill-boxes.
• I was out with a good friend of mine [who was rat arsed] when he introduced me to someone he knew from his classes. It went like this "Jen, this is Ed. See how skinny he is? You wouldn't expect him to have boobs would you? But he does!! Feel them!" My friend then grabbed my hands and I was then forced to feel Ed's man boobs [rather impressive for a skinny man] while he just stood there politely letting me. Now it's awkward whenever I see this guy.

Now I like how TWO of these points are about touching boobs.