友人と話すのが楽しかった。

friend

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

to talk; to speak; to converse; to chat; to tell; to explain; to narrate; to mention; to describe; to discuss; to speak (a language)

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

indicates sentence subject (occasionally object); indicates possessive (esp. in literary expressions); but; however; still; and

enjoyable; fun