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I'll try to give some specific examples, as this one is rather difficult to explain.

Example 1: Imagine you have been attending a kindergarten in Canada. Now you are 30 years old, so you won't go to kindergarten again, but I want to ask you whether you would be happier today, if you were attending a US kindergarten in the past. Would it be like this?

Would you like to have been attending a US kindergarten?

Example 2: You have been brought up by a stepfather. Now you are an adult, so nobody is, nor will be bringing you up anymore. But yet, I want to ask, whether you would be happier, if it were your real father who brought you up. Would it be like this?

Would you like to have been brought up by your real father?

Alternatives, or how are they different?

Would you have wanted to attend a US kindergarten?

Would you have wanted to be attending a US kindergarten?

Would you have wanted to be brought up by your real father?

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Examples 1 and 2 both correctly accomplish what you want them to. In example 1, you could be slightly more concise by rephrasing it as

Would you like to have attended a US kindergarten?

The alternatives all ask the same slightly different question. Whereas examples 1 and 2 ask the person whether he, in the present moment, thinks he would have been better off had his childhood been different, the alternatives ask the person whether he, when he was a child, would have preferred those different situations. The key difference between examples 1 and 2 on the one hand, and the alternatives on the other, is the use of the present tense like and the past tense wanted.

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  • I agree totally with your distinction, but find it interesting that Would you rather have... seems to me to cover both equally. Which I feel practically invites the other party to say whether their feeling about the matter has changed over time.
    – FumbleFingers
    Commented Mar 28, 2011 at 15:36
  • @FumbleFingers: I hear/see would you rather have used that way occasionally, but it sounds imprecise to me.
    – Kelly Hess
    Commented Mar 28, 2011 at 16:16
  • I can hardly disagree! The point of my post was to say it covers both equally, which I think by definition makes it 'imprecise'. There are potentially two different questions which could be asked, each with a variety of valid, unambiguous phrasings. Would you rather have... is common enough, and allows the hearer to choose which to answer if he wants.
    – FumbleFingers
    Commented Apr 3, 2011 at 0:04
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I would phrase these using the word rather with the present perfect tense:

Would you rather have attended a US kindergarten?

Would you rather have been brought up by your real father?

You can also phrase these with like to, though the sentence becomes somewhat more convoluted:

I would like to have learned a foreign language when I was young.

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You could phrase the first condition something like:

Do you think that you would be happier now if you had attended kindergarten in the US?

...and the second like:

Would you be happier now if you had been raised by your real father?

or

Would you be happier now if you were raised by your real father?

All five of the examples in the question are grammatically correct, although some are a bit confusing, but there are shades of differences in their meanings. For instance,

Would you like to have been attending a US kindergarten?

is different than Would you like to have attended a US kindergarten? The former goes back to the past and asks the question as if the past were now the present. The latter asks, from the present, with a view to the past.

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