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We often omit "that" in direct object noun clauses. For example:

I hope you have a good weekend.

or

I hope the meeting goes well.

It may sound a bit stilted to include "that" in those sentences, particularly the first.

However, today I was writing an email and wanted to combine those ideas into one sentence. My clarity instinct led me to write:

I hope you have a good weekend and that the meeting goes well.

In this case, omitting "that" before "the meeting goes well" makes that second object sound clumsy. But including two "that"s sounds equally clumsy.

Is it acceptable to omit the first and not the second? Does it sound clumsy to omit both?

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    It's entirely up to the speaker, and that decision probly has more to do with the way the sentence sounds -- how many syllables it consists of, and how their stress and intonation fall out -- than anything else. Sometimes you just want that extra syllable because ...
    – John Lawler
    Commented Nov 21, 2014 at 20:33
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    I hope you have a fun weekend and (that) the ski trails are well-groomed. I concur with your ear. I believe that the second clause is so "distant" from "I hope" that a "that" is needed as a kind of signal-booster.
    – TimR
    Commented Nov 21, 2014 at 23:45
  • Alternate theory: I hope you have a fun weekend and the ski trails are well-groomed, and that the hotel accepts your travel-miles in lieu of money. There, the clause that contains the "real hope" versus the "pleasantries" is introduced by "that". Or maybe the that-clause here should be called the "afterthought clause"?
    – TimR
    Commented Nov 21, 2014 at 23:50

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I don't think (that) including both sounds stilted. As always, context matters. If the conversation were about the attributes of an enjoyable Thanksgiving, and you said, "I don't care if the Turkey tastes like sawdust, as long as Uncle Bob doesn't make a fool of himself", I might respond, "I hope that Bob behaves himself and that the Turkey is delicious".

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