A calculating person thinks carefully about how to get exactly what they want, and often does not care who else gets hurt. It is not a kind word — it shows disapproval. A calculating look or a calculating move means the person is cold and planned, not open or warm. Though actually, the same letters are also just the -ing form of calculate, “to do maths,” so students sometimes hear a compliment (“good with numbers”). That is not this sense. You would not call a careful trip-planner calculating unless you meant they were selfish. It is a little formal: stories, news, and grown-up talk more than the playground.