彼と付き合うのはやめなさい。

he; him; his; boyfriend

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

to associate with; to keep company with; to go out with; to go steady with; to get on with; to go along with; to follow someone's lead; to accompany someone; to compromise

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

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

to stop (an activity); to cease; to discontinue; to end; to quit; to cancel; to abandon; to give up; to abolish; to abstain; to refrain

to do