People are fundamentally social beings and enjoy connecting with others, sometimes reaching out to otherswhether simply to say hello and to check in on how others are doing with a brief message, or to send a small gift to show that one is thinking of the other person. Yet despite the importance and enjoyment of social connection, do people accurately understand how much other people value being reached out to by someone in their social circle? Across a series of pre-registered experiments, we document a robust underestimation of how much other people appreciate being reached out to. We find evidence compatible with an account wherein one reason this underestimation of appreciation occurs is because responders (vs. initiators) are more focused on their feelings of surprise at being reached out to; such a focus on feelings of surprise in turn predicts greater appreciation. We further identify process-consistent moderators of the underestimation of reach-out appreciation, finding that it is magnified when the reach-out context is more surprising: when it occurs within a surprising (vs. unsurprising) context for the recipient and when it occurs between more socially distant (vs. socially close) others. Altogether, this research thus identifies when and why we underestimate how much other people appreciate us reaching out to them, implicating a heightened focus on feelings of surprise as one underlying explanation.