The tenth track of Confessions of a Hopeless Romantic is called “Hangover” and “at that point we are fully broken up.” It uses the metaphor of a hangover caused by alcohol to talk about the negative feelings that TJ would have after he breaks up with his girlfriend. “The lingering affects of that relationship now are I feel bitter, I feel angry, I’m upset. I don’t trust women. I have issues with intimacy now.” Pompeo says that this is the “realest” he has ever gotten on a song.

The second to last song, “Think About It,” reflects upon on the lessons he has learned from his journey of the three serious relationships he has been in. In, “Think About It,” TJ talks about being taken advantage of by a former girlfriend who seemed to be with him for the attention that she could get of other people from it, rather than caring about him.

The final song, “In N Out(ro)” is over eight minutes long and summarizes Confessions of a Hopeless Romantic. He says it includes some of the realest lyrics he has ever written, where he says,

“It its all about the looks though, and she put on a good show. But what’s the point of looking at a woman with a body if she can’t match it with a good soul.”