After the last episode, I have no idea what's going to happen with Bobby. I got to thinking about Bobby and how Sam and Dean consider him family. He's one of a very few people left in the world that knows them in any meaningful way. I grabbed some caps from episodes where there are some pretty emotional scenes with Bobby and the Winchesters. My favorites are between Bobby and Dean in AHBL pt 2 and at the end of Swan Song. It turns out a lot of them are Bobby and Dean trying to keep each other from giving up. I was surprised at how many of these scenes really resonate after last week.2.01 In My Time of Dying
SAM Oh man, Dean is gonna be pissed.
BOBBY Look, Sam. This... this just ain't worth a tow. I say we empty the trunk, sell the rest for scrap.
SAM No. Dean would kill me if we did that. When he gets better he's gonna want to fix this.
BOBBY There's nothing to fix. The frame's a pretzel, and the engine's ruined. There's barely any parts worth salvaging.
SAM Listen to me, Bobby. If there's only one working part, that's enough. We're not just going to give up on...
BOBBY Okay. You got it.
2.22 All Hell Breaks Loose - Part 2
DEAN That's my point. Dad brought me back, Bobby. I'm not even supposed to be here. At least this way, something good could come out of it, you know? It's like my life could mean something.
BOBBY What? And it didn't before?! Have you got that low of an opinion of yourself? Are you that screwed in the head?!
4.01 Lazarus Rising
5.07 The Curious Case of Dean Winchester
DEAN You don't stop being a soldier 'cause you got wounded in battle. Okay? No matter what shape you're in, bottom line is, you're family. I don't know if you've noticed, but me and Sam, we don't have much left. I can't do this without you. I can't. So don't you dare think about checking out. I don't want to hear that again.
5.10 Abandon All Hope
5.15 Dead Men Don't Wear Plaid
BOBBY Death came for me. He brought Karen back to send me a message.
DEAN You? Why you?
BOBBY Because I've been helping you, you sons of bitches. I'm one of the reasons you're still saying no to Lucifer, Sam.
5.18 Point of No Return
DEAN What is that?
BOBBY That’s the round that I mean to put through my skull.
BOBBY Every morning, I look at it. I think, “Maybe today’s the day I flip the lights out.” But I don’t do it. I never do it. You know why? Because I promised you I wouldn’t give up!
5.21 Two Minutes to Midnight
BOBBY Look, Sam's got a...darkness in him. I'm not saying he don't. But he's got a hell of a lot of good in him, too.
DEAN I know.
BOBBY Then you know Sam will beat the devil...Or die trying. That's the best we could ask for. So I got to ask, Dean. What exactly are you afraid of? Losing? Or losing your brother?
5.22 Swan Song
6.04 Weekend at Bobby's
Researching the lamia ganking on cheeseheads for Sam and Dean.
6.16 ...And Then There Were None
BOBBY So...you're Samuel.
SAMUEL You must be the guy pretending to be their father.
BOBBY Well, somebody ought to.
DEAN I mean at the end of the day, you two are family. Life's short, and ours are shorter than most. We're gonna spend it wringing our hands? Something's gonna get us eventually, and when my guts get ripped out, just so you two know, we're good. Blanket apology for all the crap that anybody's done all the way around.
6.17 My Heart Will Go On
6.22 The Man Who Knew Too Much
DEAN: Well how the hell are we gonna take out that many angels?
BOBBY: We don't. We'll ninja our way in.
DEAN: Awesome. Yeah, 'til they hear your knee squeak.
BOBBY: Shut up.
7.02 Hello Cruel World
DEAN Yeah, well. I’m not Sam, okay? I keep my marbles in a lead friggin' box. I’m fine. Really.
BOBBY Of course. Yeah. You just lost one of the best friends you ever had, your brother’s in the bell jar, and Purgatory’s most wanted are surfing the sewer lines, but yeah, yeah, I get it. You’re, you're fine.
BOBBY Course, if at any time you want to decide that’s utter horse crap, well I’ll be where I always am. Right here.
DEAN What, you want to do couples’ yoga, or you want to get back to hunting the big bads?
BOBBY Shut up. Idjit.
7.03 The Girl Next Door
DEAN Hey, look, a monster broke my leg. Oh. Wait...the house. We thought you were dead.
BOBBY Well, I ain't. Not yet. But we got to run. This place ain't safe. Where's Sam?
7.09 How to Win Friends and Influence Monsters
BOBBY What if what, Sam? You know, you worry about him. All he does is worry about you. Who's left to live their own life here? The two of you -- aren't you full up just playing Snuffleupagus with the Devil all the live long?
BOBBY Come on, now. You tried to hang it up and be a person with Lisa and Ben. And now here you are with a mean old coot and a van full of guns. That ain't person behavior, son. You're a hunter, meaning you're whatever the job you're doing today. Now, you get a case of the Anne Sextons, something's gonna come up behind you and rip your fool head off. Now, you find your reasons to get back in the game. I don't care if it's love or spite or a ten-dollar bet. I've been to enough funerals. I mean it. You die before me, and I'll kill you.
All caps from The Home of the Nutty and oxoniensis
Quotes from transcripts at the Super Wiki.