I remember talking about this at some point when I was an undergrad. What is the best way to understand "If I were you..." sentences? Taken literally, they seem to be counterfactuals with impossible antecedents (given some plausible views about identity). I don't think that's a good analysis of what we mean. One way of understanding

(1) If I were you, I would x.

seems to be

(2) If I were in your situation, I would x.

Will this work? I think it misses something. Imagine that you are trying to decide whether to x. As it turns out, though, you have good reasons not to x. I, however, do not have reasons not to x. It seems that in this situation, I could say (2), but may not want to say (1). This isn't a strong intuition, and I suspect that's because there's a closely related way of understanding (1):

(3) If I were in your situation, with your reasons, beliefs, desires, etc., I would x.

(This may be just a more detailed version of (2) if we want to include things like beliefs, desires, reasons, etc. in what we call one's situation.) Does (3) work? Imagine you're trying to decide whether to x. It seems that I can still say (1), even if I know that you have beliefs that, if true, would give you reason not to x. If I know that some of your beliefs that give you such reasons are false, it seems that I can still say (1). But, I may not want to say (3). I suppose the main reason I don't want to say (3) is that it seems to downplay the advice-element of (1).

So, is this a better way to understand (1)?

(4) You ought to x.

This definitely captures the advice element, and seems to take reasons into account. But, imagine I'm a weak-willed sort of person. Doing x requires some personal sacrifice, but is clearly what you ought to do. In this case, I would say (4), but not (1). Here's a situation. You have the opportunity to give half of your money to charity. You don't really need the money, but it's always nice to have extra. It seems that you really ought to give your money to charity. But, it seems I can truly say something like "Man, it's definitely what you ought to do, but if I were you, I wouldn't."

Thoughts?