彼はどうしてもがっこうにはいかなかった。

he; him; his; boyfriend

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

by all means; at any cost; no matter what; after all; in the long run; cravingly; at any rate; surely

in this way (used for something or someone close to the speaker, including the speaker himself, or for the opinions of the speaker); thus; such; uh... (interjection used as a verbal pause)

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 go; to move (in a direction or towards a specific location); to head (towards); to be transported (towards); to reach; to proceed; to take place; to pass through; to come and go; to walk; to die; to pass away; to do (in a specific way); to stream; to flow; to continue; to have an orgasm; to come; to cum; to trip; to get high; to have a drug-induced hallucination