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• Crowning Moment of Funny - Every scene between Damon and a newly-turned Logan in 1x10.
  Logan: I'm conflicted!
  Damon: Welcome to the club.
  • Can we extend this to every scene involving Damon and someone he either wants to gloat to or has a problem with that can't be solved immediately?
  • As well as all moments between Damon and Alaric, such as when Isobel returns to town.
  Damon: Did words completely escape you?
  Alaric: You know, I was a little too distracted by my dead vampire wife to ask any questions.
  • What, no mention of Damon when he's being flirty?
  (Stefan and Elena are being adorable and lovey-dovey in his bed
  Damon: Rise and shine, sleepy heads.
  Elena: Damon, please!
  Stefan: What are you doing?
  Damon: Oh, stop being so smutty.
  Stefan (trying to cover up Elena's scantily clad body with the covers): Seriously man, get out of here!
  Damon: If I see anything I've never seen before, I'll throw a dollar at it.

  Scenes like the above are made all the much better by Damon doing his "flirty eyebrow thing."
  • So, pretty much any time Ian Somerhalder opens his mouth?
    • Yes, except when it's a Tear Jerker or Crowning Moment of Awesome/Heartwarming.
• After Tyler notices several clues about Caroline, he finally confronts her with his suspicion that...she's a werewolf.
• In "The Descent" Caroline is kissing with Matt and shortly after that - with Tyler. She doesn't take it well:
  Caroline: "Everyone just needs to stop kissing me!"
• In "Daddy Issues" John keeps repeating to Elena that he wants to protect her. Her angry answer?
  Elena: Got it. Get in line.
• The look on Stefan and Damon's faces when they realize that they have accidentally created a secret superweapon.
• Klaus talking about the '60s, which "pretty much sucked" except for the Beatles.
• Damon's impersonation of vampires and Elena when giving a summary of what happened at the 50's dance.
  Damon: "And the vampires were all 'GRRR!' and you were all 'AAAH'!"
• Alaric needs to prove his identity, and brings up Jeremy walking in on him and Jenna while they were having sex causing Jenna to quickly say, "Okay, it's him!"
• Katherine dancing.
• Damon's half hearted attempts at apologies to Mason Lockwood and Alaric in "Ghost World"
• As Damon hides his original-killing stake under the house's firewood:
  Alaric: Did you learn nothing from the moonstone in the soap dish?
  Damon: Why, where'd you hide yours?
• Klaus and Rebekah bicker like the siblings they are, over the best way to torture Damon.