[KyleGoetz]

So what's the difference between 行っておけばよかった and 行けばよかった? Both express regret at not going. Is the former less regretful and the latter more regretful? Nagoyankee, you mention that the first has some implied lack of certainty as to whether he actually should have gone or not. Does the latter have more certainty that it's regretful he didn't go?

Thanks.

Also, then, is this a function of 〜おけばよかった in that something like 食べておけばよかった expresses some regret at not eating, but the speaker still isn't completely sure of that; rather, he's a bit on the fence still? Contrast this with the same form minus おく, in which the speaker sounds more sure that he should have eaten. Right?