Sentence 1: My friend Jay called this week. 
 Sentence 3: I asked how he was doing this summer 
 Sentence 4:  Jay said he had stomach issues all summer and lost 15 pounds 
 Sentence 5:  He said his new meds were making him feel better 
 Option 1: He was sending over some books. 
 Option 2: He was on a ski trip in Colorado.