1

ああもう、マジで彼女が複数人いるような男は普段から何してんだ。

speaker's thoughts on his futility on getting a date

...what do guys with lots of girls normally do?

not quite sure how to read 彼女が複数人いるような男, literally a guy that is similar to many girls?

3

It means:

the kind of guy who has many girlfriends

AようなB means "a B that is like A," which in English we could also translate as "an A kind of B."

Recall also that いる, like ある can mean "to have". 彼女がいる = I have a girlfriend.

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