Credit: Bob Mahoney/The CW ©2011 The CW Network, LLC Photo: Jenna's Eyes Wander in Season 2, Episode 16: "The House Guest"

If Vampire Diaries were a sitcom, Aunt Jenna’s crazy guardianship skills would provide excellent fodder for weekly storylines in which Jenna messes up, learns a valuable lesson, then cuddles up on the couch with ‘Lena, Jer’, and a pint of Chunky Monkey just in time for one last wholesome joke. But considering what we’re dealing with, we were pretty stunned in Season 2, Episode 16, “House Guest,” when Jenna said, “Because last year I was a grad student who smoked a lot of pot and couldn’t keep a goldfish alive and now I’m a parent. So I think I can handle anything, Ric.” Srsly? Jenna lives in Mystic Falls, where teen pregnancy, failing school, and partying seem to be the least of the town’s worries. At least, Jenna never seems too concerned about them. We love her and all, but when it comes to her adult supervision resume, she has some epic mishaps on the list.

Jenna would totally smoke up with Jeremy
What to do when your teenage ward is skipping school and getting high? Reminisce about your own druggie days to prove how cool you are, naturally. And then lament because your thesis and slow metabolism are the only things holding you back from indulging. Not the fact that you’re responsible for two minors. Nope, that doesn’t faze you at all, does it Jenna?
Season 1, Episode 2: “The Night of the Comet”


Credit: Bob Mahoney/The CW ©2011 The CW Network, LLC Photo: Alaric and Jenna Argue in Season 2, Episode 16: "The House Guest"

Jenna’s hot for teacher
Our favorite aunt has clearly never seen the Gilmore Girls episodes where Lorelei dated Max Medina. Parent/teacher conferences that move from classroom to bedroom never work! Oh sure, the kids act like they’re fine with it (or Jeremy straight up calls it “cruel”), but you know deep down there are some serious worlds-colliding moments happening. Such as when Elena got an eyeful of Mr. Saltzman nekkid. Or when Elena and Alaric had a heart-to-heart talk about where his relationship with her aunt was going while they were inside the high school. Sheesh. Boundaries.
Season 2, Episode 10: “The Sacrifice”; Season 2, Episode 16: “House Guest”

Jenna gets hammered
Seeing Jenna sip wine is a pretty regular TVD occurrence, but every once in a while, she likes to really hit the sauce. When Elena, Caroline, and Bonnie have a girls’ night, Jenna crashes with her Alaric drama, then promptly befriends Jose Cuervo, ditching her under-age charges for The Grill’s barstool. Of course, she also matched Matt’s manic mommy shot for shot back in Season 1, which resulted in her being too trashed to notice Jeremy was helping himself to an Anna cocktail, downing her blood like it was going out of style.
Season 2, Episode 16: “House Guest”; Season 1, Episode 16: “There Goes the Neighborhood”

Wait, where’s Elena?
Never has having a vampire boyfriend been so easy. Only Elena could get in a car accident, be driven across state lines by Damon, lie that she’s at Bonnie’s house, and totally get away with it. Then, when she wants to have a weekend alone with Stefan, Jenna happily hands over the keys to the secluded cabin with nary a warning about protection (and we’re not talking about vervaine). We get that Jenna’s ‘shipping on Stelena hardcore, but when Uncle John, who ranks among the world’s worst fathers, questions whether you’re fit to be a guardian, well, maybe it’s time to attend a parenting class or two.
Season 1, Episode 9: “History Repeating”; Season 2, Episode 14: “Crying Wolf”