- The monologues between Miles and Maya on Stephanie's porch. He tells her why he loves pinot noir, and describing himself at the same time. She tells him how even in its decline, wine's still worth tasting, describing her feelings for him simultaneously.
- After all their misadventures and blow-ups on the trip, it is pretty heartwarming to see Jack and Miles embrace before going back to their lives still best buds.
- In the ending, Jack and Miles get back from the trip, and it seems that Miles got the bad end of the stick. He's right back where he started, his book didn't get published, he meets his now pregnant ex-wife and her husband who are getting along fine, and he just lost the one girl he wanted to date in years, and she might not have even finished his manuscript. It's all rather depressing and bleak... but then he gets a message from his answering machine. It's Maya, she's just now finished Miles' book and praises it while commenting on certain parts proving that she did in fact read it (unlike Jack). She then goes on saying how it sucks it didn't get published and how she really appreciates the letter Miles wrote. The message ends with her wanting to hang out with Miles again, as we see Miles knocking on her door.
- It was getting so bleak at the end for Miles that when he drives away from the reception and makes a rush for his closet door, Giamatti notes on the DVD commentary that he was told by several viewers that they assumed he was grabbing something so he could kill himself.
Heartwarming / Sideways