Nice to see Kisaki is letting him reach his low point before she raises him back up again as someone who only looks at her.
Though I'm honestly not sure how intentional it is for her that things worked out exactly this way, and how much she understands his current thought patterns, I do think that she probably figured that he'd work up the courage to jump like this one day, and so it made sense to have her by his side when it happened so that she could both observe his reaction and be there to catch him on the potential rebound (which indeed happened to be the case).