That awkward moment when...

[Neriad13]

...a bandit holds you up on the road demanding 200 gold...as your armored troll bodyguard stands directly behind you. "Lady, surely you've got more to live for! No, then? Well... rip 'er head off Franklin."

 

[Neveraine]

That awkward moment when a random thief dies in Riften and you go and loot his body for the valuables that he stole and no one cares.

 

[bulbaquil]

That awkward moment when a NPC refers to "Ysmir's Beard" and you are playing a female dragonborn.

"but... I don't have a beard!"

Because you know... the Greybeards give you the title Ysmir or something like that.

That awkward moment when you think you have made a clever joke only to realize you might not know what you are talking about.

Ysmir is Talos... I think.

--That awkward moment when an opponent's blow causes your Light/Heavy Armor to improve, triggering a level-up... but also kills you in the process.

 

[Neriad13]

...you and Serana are visiting Meridia's temple when suddenly Meridia lifts you up thousands of feet above the ground to talk to you. Serana casually watches you drop back down and the moment you land, coyly remarks "I was always told to avoid these types of ruins. Now I think I see why."

 

[Uther Pundragon]

... you realize that Spriggans can't be made into firewood nor turned into a mobile torch for darkened caves.

 

[bulbaquil]

That awkward moment when you try to enter Radiant Raiment, but out of habit you enter Bits and Pieces instead.

 

[Neriad13]

...you see a mudcrab going over a waterfall.

...a necromancer kills, reanimates and sicks your armored pet frost troll on you in the middle of a fight.

 

[daedalus93]

That awkward moment when this:

Bonus points if someone else who's never played Skyrim is in the same room as you.

 

[Neriad13]

...you accidentally nail Jouane Manette in the back of the head with a crossbow bolt with a critical hit, just as he's running to help out in a vampire attack. Furthermore, you're in full sight of the town guards as it happens, none of whom seem to mind terribly about the murder that's taken place. Or that your companion then reanimated his corpse to continue the fight that he never finished.

 

[Kittibear]

...you already have the Dragonstone before being tasked to go to Bleak Falls Barrow.

 

[Kittibear]

...you hit someone with an arrow so hard that they go flying at least 20 feet back. Okay, that's actually quite hilarious when that happens.

 

[Neveraine]

That awkward moment when you blackmail Haelga and wonder "Can I blackmail her, so that she shows me her Dibellan arts?"

 

[KittyTheKitty]

That awkward moment when you pay a Thieves Guild member for lessons and send your follower to kill him so you can take your 22,000 coin back and the Guild shuns you.

 

[DdraigGwyn]

When you charge into a bandit-filled cave just as your Bound Sword evaporates.

 

[Octavia]

... When someone says "I'll have your head!" just as you decapitate them.

 

[Neveraine]

The awkward moment when you try to pickpocket people from the thieves guild and they catch you, but they don't care at all.

 

[bulbaquil]

That awkward moment when this happens:

Imagine you're the prisoner.

 

[KittyTheKitty]

That awkward moment when you want to kill Astrid so you can marry Arnbjorn, but later find out after feverishly searching for him that he died. :'(

 

[Neriad13]

...you press the wrong button and accidentally wing a prized Daedric artifact behind Belethor's counter. Belethor only smiles and sneers "One person's trash is another person's treasure. Don't be surprised if you find that gone." Needless to say, you do a flying leap over the counter, tackle the sleazeball and snatch it back up as quickly as you dropped it.

 

[bulbaquil]

...you press the wrong button and accidentally wing a prized Daedric artifact behind Belethor's counter. Belethor only smiles and sneers "One person's trash is another person's treasure. Don't be surprised if you find that gone." Needless to say, you do a flying leap over the counter, tackle the sleazeball and snatch it back up as quickly as you dropped it.

Belethor would do that, too.