Career Night: Elena knows Stefan's just there to look out for her. Things are tense between them, so Stefan tries to make small talk about his past. He wanted to be a doctor, but once he was turned, he couldn't handle working around blood. He tried lots of other things over the years and loved them all, but he moved on before anyone noticed he never aged.
Sidebar: Here's a word of advice to the writers -- don't hit that ageless point too many times. Paul Wesley is a beautiful, youthful, 27 year old specimen, but with any luck, this show will go five years or more. If/since it's really pushing it to sell a beautiful, youthful 27 year old as a 17 year old, imagine the challenge once he's 32 years old. I mean, in five years, Wesley's looks are going to change, noticeably, and probably more so than anyone else in the cast. Now, they won't change for the worse. He'll grow even manlier and more appealing. But still? No matter what anyone does, he will not look more childlike. Check out David Boreanaz in season 1 of Buffy the Vampire Slayer and then take a gander at him in season 3, and then throughout the life of his spin-off series, Angel and you'll see what I mean. If you ever retcon Stefan's age-at-siring with an "he lied about it so Elena wouldn't freak," or "Daywalkers don't age, but they appear to, if ever so slowly, because of their exposure to the sun," I've got your backs. Okay, back to the show.
Elena wonders how long it took each time before Stefan had to pick up stakes (oh, sorry). He always had to leave after a few years at most. He didn't have a choice. He tries to change the subject and asks Elena about her plans for the future but she resists. "I don't want to talk about my future, Stefan, because everything you're saying is making it perfectly clear you're not going to be in it." He stammers that it's not that he doesn't want to be in her life. She cuts him off. "You can't. I get it. I heard you the first time and the second time. I appreciate you looking out for me, but please, if you're going to leave -- then just go." Anya whines, "I'm tired and I don't really feel like taking a tour of beautiful things I can't have." Amen.
Jenna hustles over and interrupts the awkward conversation, asking Elena to hide her. "The Scum Fell has landed." When Stefan realizes they're talking about Logan Fell, he takes off into the hallway because, of course, he knows Logan should be dead. Stefan gives him the evil eye. Logan returns a cheeky wave. Their glares carry us into... Commercial.