"(o≚‿≚)ʕᵔᴥᵔʔ" is an emoticon depicting a face with rosy cheeks and a bear nose and ears. It can convey a sense of cuteness, playfulness, or affection. "He always sleeps with a bear" emote likely refers to a Twitch emote featuring a cartoon bear sleeping on a pillow. It may be used to express relaxation, comfort, or contentment.