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The sentence is:

I wonder sometimes if he even knows what 'fun' means, but I guess he wouldn't be in Harvard if he didn't.

Or is it "... if he doesn't"?

And at the front portion, is it "if he even knew" or "if he even knows"?

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I wonder sometimes if he even knows what 'fun' means, but I guess he wouldn't be in Harvard if he didn't.

This use of didn't is not the past tense. It is the subjunctive mood.

The subjunctive mood expresses hypothetical or imaginary situations. Often in the subjunctive mood we use the past tense form of a verb even when discussing events that might occur in the present or near future.

For example,

I would go to the play if my favorite actor was performing

or

What would you do if you had a million dollars?

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The way you have it now is grammatically correct. The text below is just digging a bit further into how you would use the other words you mentioned.

One example that may clear it up is this "He doesn't know how to read" means he currently does not know how to read. "He didn't know how to read" means he previously did not know how to read.

If you say "I wonder if he even knew" you're saying you wonder if he had certain knowledge at some previous time. If you say "I wonder if he even knows" you're saying you wonder if he currently has certain knowledge.

You could say "I guess he won't be in Harvard long if he doesn't".

Or lets say you were talking about whether or not he'd turned in a vital assignment, "I guess he won't be in Harvard long if he didn't". Meaning if he didn't turn in the assignment, surely sooner or later he will be expelled.

Lets say you wanted to use "if he knew". You would have to do something like this:

I wonder sometimes he even knew what 'fun' meant, but I guess he wouldn't be in Harvard if he didn't.

Forgive me if you know all this, but meant is the past tense of mean. I think you could actually still use "means" and it would be grammatically correct, but if you asked me, if you don't want to use "meant", it would still be better to say something like "I wonder sometimes if even knew what 'fun' was" or "I wonder sometimes if even knew the meaning of 'fun'"

and to use "if he doesn't" it would go something like this like this

I wonder sometimes if he even knows what fun means, but I guess he won't be in Harvard long if he doesn't"

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  • Having made copious edits to your punctuation and minor spelling mistakes ( have you heard of the apostrophe?), replacing instances of a small i with a capital I, I think I am now in a position to comment on the content. I am not entirely comfortable with the tense matching in your second from last quoted sentence. I wonder (present) sometimes, if he even knew (past) what 'fun' meant (past), but I guess he wouldn't be (present) in Harvard if he didn't (present). – WS2 Nov 8 '16 at 10:55
  • Thank you for fixing it up. Maybe it is wrong, I'm not sure. The way I see it, this is the way you would express that you currently wonder if he previously knew what fun meant (in part bc "he", back during whatever time, wouldn't necessarily know todays meaning of a word), but I guess he wouldn't be in Harvard if he didn't (i guess this should be hadnt? i was thinking of sentences like "if he didn't do it, then who did?" and in that examples it seems (to me) as though didn't refers to something in the past.) (isn't do, don't, does, and doesn't the present?) – pau Nov 8 '16 at 14:15
  • The problem is with the word didn't at the very end. You rightly say that it is in the past tense. But it nonetheless implies the present, due to it being part of a conditional clause. With conditionals there is a tense shift. As I am a native speaker I only understand this intuitively, and have never studied the rules. But rules do exist and you should consult them. I wouldn't give him the job if I didn't like him. That is all happening in the present. But I wouldn't have given him the job, if I hadn't liked him is how we express a past circumstance. – WS2 Nov 12 '16 at 13:43

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