Evolution of a Bad relationship in 23 Songs

Meant to be a conversation.
Beyond that, the less I explain, the better.

1) Today, The Smashing Pumpkins
2) Gravel, Ani DiFranco
3) Sinkin’ Soon, Norah Jones
4) Little Earthquakes, Tori Amos
5) Little Plastic Castle, Ani DiFranco
6) Careless Love, Madeleine Peyroux
7) When Doves Cry, The Be Good Tanyas
8) We Can Work It Out, Paul McCartney acoustic
9) Straighten Up and Fly Right, Nat King Cole
10) Oh! Darling, The Beatles
11) NY, I Love You but You’re Bringing Me Down, LCD Sound System
12) Sweet Ride, Tanya Donelly
13) I’m Sticking with You, Velvet Underground
14) If I Only Had a Brain, MC 900 ft. Jesus
15) Othello, The Dance Hall Crashers
16) Grounds for Divorce, Elbow
17) Poems, Tricky
18) Turn on Me, The Shins
19) Big in Japan, Ane Brun
20) Don’t Think Twice, It’s Alright, Dylan
21) Von Hier an Blind (Blind from Here on) , Wir Sind Helden
22) If Love was a Train, Michelle Shocked
23) Ecclesiastes: Free My Heart, Me’Shell Ndegeocello