1. Many people look forward to the New Year for a new start on old habits.

Question

[What is the meaning of 'on'? Is 'on' 'about' here?]

2. Happy New Year. Here’s to another year pretending that I like you people.
[Do we have to use 'to' in the second sentence? Does 'pretending ....' modify 'another year'?]

Answer 1

I think it means a new start on efforts to break old habits that one doesn't want to continue. If one has tried to quit smoking (or eating too many sweet desserts, whatever the bad habit is) and not succeeded, the New Year is a time to try again, work on it.

Answer 2

Thank you. Is 'on' similar to 'about'?

2-2. Happy New Year. Here’s another year pretending that I like you people.
[What about this sentence? 'to' is deleted here. Is 2-2 okay?]

Answer 3

2-2 is grammatically correct, but it's a rather negative wish for someone else's new year! Did you intend it to be negative?