Romances in this game are linear, you just work to unlock them.
VNs condition us that if something bad happens, we did something wrong. However, relationships in real life aren't perfect. Confessions can be made and not accepted - but still come together later on. Part of the reason there is little to no story choices is to not give the impression that difficulties in these relationships are in any way your fault.
Robin has difficulty seeing Emmitt as an adult in the beginning of their path. That is no reflection of you, the player. It's simply a story I wanted to tell. Keep playing! :)