4

When should I write the word "to" twice?

"ways to .. and to .. "

When should I omit the second "to"?

"ways to .. and .. "

I want to ask a person "What are the best ways to climb over a wall?" and also ask him "What are the best ways to start a conversation with a girl?"

Which of the following sentences should I use?

What are the best ways to climb over a wall and to start a conversation with a girl?

What are the best ways to climb over a wall and start a conversation with a girl?

3

If you use to only before climb, it implies that you want to climb over a wall in order to start a conversation with a girl.

If you use to before climb and start, it implies, but doesn't guarantee, that you're asking how to do two separate things: (1) climb over a wall and (2) start a conversation with a girl.

Many native Anglophones won't see a difference between your sentences. The problem, as I see it, is that there isn't enough information in the question to make clear to the person you're asking whether you're asking one question or two.

In speech, it might be possible to make your intentions clear with stress and intonation, e.g., by strongly stressing and with two to's.

In writing, it should be possible to make your intentions clear with formatting, e.g., by making a list:

What are the best ways to:
(1) climb over a wall
and
(2) start a conversation with a girl?

I'd suggest adding something that immediately disambiguates your question, e.g.:

I have two unrelated questions. What are the best ways to climb over a wall and
to start a conversation with a girl?

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