i-adjective
provoking; rather annoying
Describes someone or something that is mildly irritating in a way that is hard to ignore, often with a hint of grudging admiration or cuteness. The prefix 小 softens the annoyance.
彼の小憎らしい笑顔が忘れられない。
I can't forget his provoking smile.
あの子は小憎らしいほど賢い。
That kid is smart to an annoying degree.
i-adjective
Used ironically to call someone darling or cute when they are actually being a bit annoying. Often affectionate teasing.
小憎らしいやつだな、お前は。
You're a darling little thing, aren't you? (ironic)