彼は、彼女のことを気の毒に思わずにはいられなかった。

he; him; his; boyfriend

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

she; her; her; girlfriend; sweetheart

indicates possessive; nominalizes verbs and adjectives; substitutes for "ga" in subordinate phrases; (at sentence-end, falling tone) indicates a confident conclusion; (at sentence-end) indicates emotional emphasis; (at sentence-end, rising tone) indicates question

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.

pitiful; unfortunate; (a) pity

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 think; to consider; to believe; to think (of doing); to plan (to do); to judge; to assess; to regard; to imagine; to suppose; to dream; to expect; to look forward to; to feel; to desire; to want; to recall; to remember

to need; to want