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A: He is the worst person to talk to.
B: Houston is annoying fly to.

Comments  

Sentence A "He is the worst person to talk to" is a grammatically correct sentence that means the person referred to is not a good person to talk to.

Sentence B is not correct.

A corrected version of sentence B would be "Houston is annoying to fly to".

anonymousA: He is the worst person to talk to.

Yes, correct.

anonymousB: Houston is annoying fly to.

I'm sure you meant to type "Houston is annoying to fly to." It's a little convoluted, but I would not be surprised to hear it in everyday conversation.