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Which is correct?

I would like to go to a youth center to help and work with teenagers.

I would like to go to a youth center to help and to work with teenagers.

The question is whether to needs to be repeated in the second infinitive.

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I like this one better than either of those (although some may say the meaning has shifted): I would like to go to a youth center to help work with teenagers. – J.R. May 2 '13 at 21:42

I would use the second infinitive, to clearly convey what I think you want to convey.

The issue I have with the first example,

I would like to go to a youth center to help and work with teenagers.

is that, because of the undivided phrase "to help and work", structurally speaking, you're saying two things:

  • That you want to work with teenagers
  • That you want to help with teenagers

And I don't think you want to say that you are "helping with" teenagers. That makes it sound like you're helping a parent handle their unruly teenage children, as opposed to actually helping teenagers themselves.

If you use the latter construction, dividing the phrase into separate infinitives, it makes it clear that you want to help teenagers, and that you want to work with teenagers.

A simple test to see whether you should use a second "to" in a sentence is to switch the order of the words connected by "and":

I would like to go to a youth center to work and help with teenagers.

... that sounds horrible, so keep the second infinitive.

An alternative solution would be to say

I would like to go to a youth center to work with and help teenagers.

though personally I think that sounds awkward.

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Your first point is ambiguous, though. You're right about this: If I said "to help and work with teenagers" I'd be saying two things. We both agree that one of those is that I want to work with teenagers, but the "help" part is ambiguous. There are plenty of ways I could help at a youth center, without working with teens. I might be an accountant who is willing to help with their finances. I might want to organize a fundraiser. I might want to offer janitorial services in the bathrooms. I could want to do any of these and say, "I want to go to (help) and (work with teenagers)." – J.R. May 4 '13 at 8:16
Helping at a work center is different from helping teenagers. If you want to help at the work center, I would probably say exactly that, rather than leaving the word "help" with no direct object and assuming that it will be read as such. You're right, though, that is ambiguous - however, personally, when I read it the first time, I read it as "I want to go to (help) and (work with) teenagers." – Cmillz May 4 '13 at 15:45

Since "to work with teenagers" is a form of "helping", I would say you are safe to omit the to.

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On a different note, I think "you are safe in omitting the to" or "it is safe to omit the to." – Kris May 4 '13 at 11:34

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