In order to trigger Elliott's two heart events, you'll need to build a friendship with him. To do this, you must give him gifts he likes (such as seafood or flowers) and talk to him every day. When his heart meter reaches 2 hearts, the first event will trigger. After that, keep talking and giving gifts until his heart meter is full (4 hearts). Once it is full, the second event will be triggered. Remember that each character has different preferences when it comes to gifts so make sure you check out what presents they like before buying them anything!