I would guess during the year with Lisa, if not when he came back from hell. I don't think he would have needed anything more than alcohol before that.

We know he's no stranger to the occasional bong hit, etc., but that's recreational. The way he said "effective" made me think of someone using to sleep and forget, and it makes the most sense it would have started during the year with Lisa, when he had the most to forget.

It's also incredibly easy to get prescription meds in the suburbs, and it could have been where he got the idea in the first place.

I had the impression that the pills are more of an extreme measure and aimed more at physical pain than psychic, whereas the alcohol is a more constant crutch. Thinking about it now, I don't know how I got that from the one scene.

I found the Lisa-opens-the-door-to-Dean montage hilarious. Like, that's their whole relationship - he shows up and she reacts.

It's also incredibly easy to get prescription meds in the suburbs

Maybe I should move, then.

that the pills are more of an extreme measure and aimed more at physical pain

Wasn't he offering them to Sam for mental relief? Physically Sam was okay.

The way he was pinching his nose and saying he felt like he got hit with a planet said physical aftereffects to me.

I found the Lisa-opens-the-door-to-Dean montage hilarious. Like, that's their whole relationship - he shows up and she reacts.

Hah! This also occurred to me when I was watching.

Wasn't he offering them to Sam for mental relief? Physically Sam was okay.

I thought it was for the physical pain. Sam was rubbing his head like he had a pretty vicious headache. Then again, I think I made up a little narrative in my head to explain that scene. I found the pills a bit unexpected.

Maybe I should move, then.

Well, I didn't say legally.

Dean may have meant physical pain in part, but bundling it in with the whole DENY! REPRESS! speech, I definitely thought it had more to do with getting a dreamless night's sleep than anything else.

I thought he was suggesting it like he suggested alcohol, but I can see that.

Regardless of the accuracy of what I've already said, it seems pretty clear that Dean hadn't offered prescription bottles to Sam before, so I'm thinking they are a post-Hell sort of thing, timing-wise.

Eta: the pills were bundled with the coffee and food for fixing what's wrong with you now. It was just alcohol and violence for the repression. FWTW

I thought the pills were for physical pain as well; the violence and alcohol were for the psychic.

Also, Lisa called Dean six times and he never called back? Wait? What? Wasn't Dean calling her over and over and she wasn't answering? I prefer that version of the story and I'm sticking to it.

Yeah, I seem to recall that from earlier in the season too. You don't get to repeatedly stonewall someone's attempts to contact you and then be all outraged at them for doing the same to you afterward.

Lisa's absolutely in the right to have kicked Dean to the curb for Ben's wellbeing and her own, but doing so is not compatible with blaming him for leaving.