Most Awkward Moment?

[Toranilor]

I have three;

A couple of years ago I ripped a set of pants playing dogeball. Embarassed, I went home (I live nearby) to get changed. I inadvertently wore the ripped pair the next day. To a university day with hundred of others.

A friend and I were previewing our graduating class' farewell presentation. He complained that the video was 'too dark'. Instinctively, I blurted out "You're too dark!", as a joke. (These sort of jokes are common amongst my friends and I). After a brief second I remembered he was Indian.
This happened twice.

This one was my work manager, but nonetheless awkward;
After giving her my mobile number to arrange shifts, I got a message from my manager at 2AM
asking if I was going to meet her at the bus stop. 15 minutes later I got another text telling me that everyone was dissapointed that I diddn't show. I confronted her about it the next day at work, turns out she was drunk and got her numbers mixed up.

 

[Auron225]

My friend got a girlfriend and he, I, and her (awkward third-wheel-ness) went to see a movie. Afterwords we were all picked up by my friend's dad in a van. My friend's dad was in the driver's seat, I was in the middle row, and my friend and his girlfriend were in the back seats and I had to talk to/distract my friend's dad talking about the movie while seeing my friend and his girlfriend kiss in the back seat through the rear-view mirror...

I can top that one... why I'm happy I can top it Im not exactly sure.

Same sort of deal, except - I was stuck in the back-seat WITH the couple! =O And at the time - I happened to like the girl in the relationship... and she was leaning against me to make-out with her boyfriend... *shivers* The Ultimate in Third-wheel goodness!

 

[Auron225]

Oh - there's also the time I was sitting with a friend and some friends of that friend I had just met. I had heard their names but I wasn't really paying attention at the time. Anyhow - we were talking about ridiculous names that parents would name their kids, when I come out with;

"One name I just don't get is Ruth! Who on Earth would think of naming their child that!?"

...which is when I realized a friend of a my friend was in fact called Ruth... ohh my the awkwardness!!! XS

 

[SeriousSquirrel]

Change whatever I said to the entirety of last Saturday. I'd do a lot of things to undo the events of that day

The only awkward moments that readily come to mind are whenever I have told a girl that I like her.

Yeah, I'm pathetic.

I feel your pain man, I feel your pain

 

[ViaticalTarsier]

Being known as a good skier and in front of like 200people falling off the chairlift at the load point because the lifty was being funny and held the chair back causing me fall off the lip of the seat and forcing the chairlift to stop as I crawled out of the way with my skis and poles going everywhich way. That was probably the most awkward but it wasn't too embarrassing I still get made fun of for such a beginner move but its something to laugh about now...... I usually never feel awkward since most of the time I just roll with whatever comes my way.

 

[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.