In the early 2260s, Crandall was attending Starfleet Academy on Earth at the same time as Pavel Chekov, though the two never met until their final year at the Academy. Shortly after meeting they began a romantic relationship which led Chekov to propose to her following their graduation. Unfortunately, Crandall turned down the proposal because they could find themselves serving on different starships and ran the risk of never seeing one another again. Crandall's prediction played out when Chekov was assigned to the USS Enterprise and she received a different assignment.
However, six months later she was reassigned to the Enterprise to participate in the ship's survey mission to the Mariotian sector. The two had an emotional reunion, but while Chekov wanted to continue their relationship from where they left it, Crandall wanted to take things more slowly because she felt that she had changed as a person over the preceeding months. (TOS comic: "No Compromise Part One")
Unfortunately, Crandall was killed in unspecified circumstances in 2290. While she hadn't seen Chekov in over twenty years, she left instructions that he was to be notified of her death. (TOS comic: "No Compromise Part One")