[Nagoyankee]

Originally Posted by 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?

The difference between 行っておけばよかった and 行けばよかった has more to do with the personality than how much one regrets not going. It's really difficult to say which one regrets more from these short phrases alone.

行っておけばよかった would be said by someone very indecisive not only about this particular event but also about things in general. Saying 行っておけばよかった a day after the concert is of no use. It's like he's still vacillating, which is way too late to do.

行けばよかった is much simpler. Someone tells you the concer was great and you say, "Oh man, I should have gone with you, then." This person probably wouldn't go on thinking about it.

Regarding your next question, it's also hard to say which one shows more regret from the phrases 食べておけばよかった and 食べればよかった alone. The way you say those can change the degrees of regret, too, which is an important factor in spoken language. But generally speaking, I would say that by using おく, you can show more regret. This is because, by using it, you sound like you're criticizing yourself for the bad decision-making.