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I'd like to fully understand how to use 'too..to..' sentence pattern.

Here are 2 examples.

  1. You are too pretty to be my girlfriend, because I'm ugly.

  2. You are too pretty for me to ask out, because I'm ugly.

Here, 'you' is used as a doer(subject) of 'be my girlfriend' in sentence #1, and used as an object of 'ask out' #2. right?

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You understand this correctly.

This fullest form of this comparative construction is

too ADJECTIVE [for SUBJECT to VERB COMPLEMENTS]

The piece in square brackets [] is what we call an infinitival clause: it has its own SUBJECT, VERB and COMPLEMENTS, with VERB cast in the infinitive (to VERB). 

     SUBJ  VERBinf  COMPL  
[for  me   to take   out  ]

The entire comparative construction (too pretty for me to take out) "acts like" a single adjective modifying a noun or noun phrase. In your sentence it is a predicate adjective modifying the subject of the main clause, you, in exactly the same way as the bare adjective pretty would. In the next graphic the pieces which act like adjectives are enclosed in curly brackets {}.

You are { pretty }.
You are { too pretty [for me to take out] }.

There are two different ways of using the construction.

  1. If the subject of the infinitival clause is different from the word which the construction modifies, then you use the full infinitival, with for SUBJECT. In the graphic below I've marked the word modified with '1' and the subject of the infinitival with '2'

    You1 are {too pretty [for me2 to ask out]}.

    As you say, you is understood to be the missing term in the infinitival: the direct object of take.

  2. But if the subject of the infinitival is the same as the word which the construction modifies, for SUBJECT is deleted. In the graphic below I've marked both the word modified and the subject of the infinitival with 1

    You1 are {too pretty [for you1 to be my girlfriend]}.

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  • I appreciate your good explanations but this one is over my head , i.e. I don't try to follow your explanations, they are too levels too high. It is a relatively simple construction and it is not necessary to use the whole apparatus of linguistic terms to explain it. Reminds me of some explanations of John Lawler.
    – rogermue
    Jul 9, 2015 at 18:43
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    @rogermue I have simplified as far as I can; but OP asks to "fully understand", and I feel some depth is called for. I suggest that it is not at all a simple construction, although once you have learned how to use it you can ignore its complexity.
    – StoneyB on hiatus
    Jul 9, 2015 at 22:20
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I would not see it so complicated. You could transform sentence 2 thus: You are too pretty for me to ask (you) out. This way you see that the second "you", the object after "to ask", was omitted as it is self-evident.

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  • How about *These shoes are too old to wear"? Would you understand that as omission as well? ... too old (for me? for anyone?) to wear (them)... Or would it translate to "are unwearable because they're too old"?
    – TimR
    Jul 10, 2015 at 12:38
  • I don't think that there are problems with that structure. Of course, if some- one has difficulty you could explain it as you do or with " are too old for wearing".
    – rogermue
    Jul 10, 2015 at 12:54

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