Wilson first meets Ashley when he goes to see Tucker in the emergency room. At first he mistakes her for Tucker's daughter Emily. However, when he sees Ashley has a cold sore, he thinks it may have given Tucker transverse myelitis and he starts treating for it.
As Tucker gets sicker, Wilson decides to call Emily and she arrives with Tucker's ex-wife Melissa. Melissa is concerned and when they realize Tucker has cancer, Tucker seems to be reconciling with her, even appointing Melissa as his medical proxy.
However, when Tucker recovers, he goes back to Ashley, telling Wilson the people you want with you when you're going to live are different than the ones you want when you're going to die. When Ashley calls Wilson "Jim" just like Tucker does, he quickly corrects her and says he prefers "James".