Most Awkward Moment?

[steevee]

Oh, so, so many instances. So many *shudder*

Latest would be doing PT with Cadets. I'm 16, there's a girl there that likes me, but she's not turning 15 for a couple of months. But she's, uh, rather developed.
Anyway, I'm running the running section. She's definatley not wearing a sports bra. Then I have to tell all my friends to stop gawking, which my CO overhears and now thinks I'm a pervert.
Add to that, that same girl was later sat down and, ahem, 'revealing' her ass somewhat. Unbeknownst to her. Once again, I tell my friends to put their eyes back in their heads. Then one of them says that she's not wearing underwea, so I blurt out that I'm sure she's wearing underwear. I turn round, geuss who got up and came over to talk to us?
Yeah........

 

[DanTheMan92]

Prior to a break up with my ex (this didn't help matters of the relationship at the time) I was on the phone to her friend, and not knowing she was with her and on speaker phone, and started slating her not knowing she could hear my every word...It was quite awkward yet I was kinda smirking to myself as I was already planning on breaking it off...

 

[MagnificentFiend]

My first girlfriend's Mum walked in on us. Doggy-style. On the floor.

I want to hear more about this, what did she do, what did you do, what did her mom do? I am very, very interested.

Her Mum, who I'm pretty sure knew what was going on and just interrupted for a laugh, said something brief and left as quickly as she entered. My then-gf cried 'cause she thought she was going to get into trouble. I was just mortfied and tried my best to reassure her that it'd be ok. Nothing came of it in the end, bit of a disappointment as horrendous stories go.

 

[Zaverexus]

Also, the same girl getting mad at me because I won't tell her who the girl is that I like. It would be even more awkward if I just said "You." when she asks.

I actually did that once. One of my friends who is a girl found out I liked someone (didn't know she was the one) and kept asking me about her, but never for her name, so I answered all the questions truthfully and she still had no idea who it was. Then I just came straight out and told her that I was talking about her the whole time... uber-awkward, you have no idea.
XD but now she's my girlfriend so I guess it all turned out in the und.