いくら親しいからといってそんな事を彼に頼めません。

how much?; how many?; even; even if

intimate; close (e.g. friend)

from (e.g. time, place, numerical quantity); since; from (originator); by; because; since; out of (constituent, part); through (e.g. window, vestibule); after; since

if; when; and; with; particle used for quoting (with speech, thoughts, etc.); quoting particle; promoted pawn; indicates question (sentence end)

to do up (hair); to braid; to fasten; to fix

such (about the actions of the listener, or about ideas expressed or understood by the listener); like that; that sort of

thing; matter; incident; occurrence; event; something serious; trouble; crisis; circumstances; situation; state of affairs; work; business; affair; after an inflectable word, creates a noun phrase indicating something the speaker does not feel close to; nominalizing suffix; pretending to ...; playing make-believe ...; alias; aka; nickname; alternative name; also known as

indicates direct object of action; indicates subject of causative expression; indicates an area traversed; indicates time (period) over which action takes place; indicates point of departure or separation of action; indicates object of desire, like, hate, etc.

he; him; his; boyfriend

at (place, time); in; on; during; to (direction, state); toward; into; for (purpose); because of (reason); for; with; by; from; as (i.e. in the role of); per; in; for; a (e.g. "once a month"); and; in addition to; if; although