the awkward moment when you stare at your opponent to intimidate him, but when it instead turns him on.
100 awkward moments in a game of chess

That awkward moment when you are trolling, calling your opponent all sorts of nasty names, and come to realize you've been playing against your mother.

that awkward momont when you cant stand up because you've been staring at your female opponents chest and well.. you know the rest.
Lol...
That awkward moment when yoiu stare at a female opponents chest and be like "wow, more hairy than mine" then you realize she's a male.

(100.1131) That awkward moment in a speed game where you warn yourself NOT to make one specific move, your time goes down to the one minute mark, you panic, and then you make the move you just told yourself not to ever make. And, of course, you immediately lose after that. (This happened to me yesterday.)

Lol that awkward moment in a live game when you want to castle and instead of moving the King you move the rook. The King remains in his square and the rook ends up completely misplaced

that awkward moment when your opponent has an enormous beard that covers some of his pieces so you get tough with him and shave it off yourself!

(100.1132) That awkward moment when chess.com switches your account with opponent's account.
"....... And for that one epic moment, i was an Indian with a platinum membership...."

(100.1132) That awkward moment when chess.com switches your account with opponent's account.
"....... And for that one epic moment, i was an Indian with a diamond membership...."
Did that really happen to you?! XD
(100.1133) That awkward moment when you log in to find that you have 30 friend requests from random people you don't know and don't want to know. (I once got a friend request from some mystery person who has a lot of friends.)

(100.1132) That awkward moment when chess.com switches your account with opponent's account.
"....... And for that one epic moment, i was an Indian with a diamond membership...."
Did that really happen to you?! XD
Lol.... the pix says it all, i think it was just a minor bug.
That awkward moment when you register for a team match, and then cancel it on seeing your opponent who is +500 higher rated than you.

That awkward moment when you press the 'send move' button and you close your eyes lest you spot a horrible blunder

That awkward moment in online chess when you have a mate in 3 and opponent goes a on long vacation but you see him online all the time and you be like...

(100.1137) That awkward moment when you beat your opponent, he/she says "Good game," and then adds "Not" while you're turning away from him/her.

Akward moment when you drop a piece and don't realize it till later
Lol! That has actually happened to me before (though thankfully not for a while).
"Hang on! I'm actually down in material here!"

(100.1141) That awkward moment when you easily beat a tactics problem that has a rating much higher than yours and then completely mess up in a tactics problem that has a rating much lower than yours.
BlackKnight and egoole it has happened to me..6 times blunder noticed
after submited by mouseclick. in this 2 times escaped as my internet conn.slow ,so unplugged and transmission didn't carry through.in a current game I am
at the gaining end ,my opponent in 3 days TM did exactly as u said his
rating is 1797 and now rues his mouseslip.I sympathised withhim on chat..
that awkward momont when you cant stand up because you've been staring at your female opponents chest and well.. you know the rest.