彼はこれまでこんな苦境に立ち至ったことはなかった。

he; him; his; boyfriend

topic marker particle; indicates contrast with another option (stated or unstated); adds emphasis

this (indicating an item near the speaker, the action of the speaker, or the current topic); this person (usu. indicating someone in one's in-group); now; here; I (me); certainly

until (a time); till; to; up to; to (a place); as far as; to (an extent); up to; so far as; even; only; merely

such (about something or someone close to the speaker (including the speaker), or about ideas expressed by the speaker); like this

trouble; crisis; predicament; squeeze; pinch

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

to come to (a serious state); to reach

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

nonexistent; not being (there); unpossessed; unowned; not had; unique; indicates negation, inexperience, unnecessariness or impossibility; not ...; to not be...; to have not ...