| 0 | Love Stinks Issue | cover | 1 | pencils: Mark Fredrickson; inks: Mark Fredrickson; colors: Mark Fredrickson | Taylor Swift; Alfred E. Neuman [as Travis Kelse] |
| 1 | - | table of contents | 2 | pencils: Norman Mingo; inks: Norman Mingo; colors: Norman Mingo | Alfred E. Neuman |
| 2 | A Mad Look at Dating | comic story | 3 | script: Sergio Aragonés; pencils: Sergio Aragonés; inks: Sergio Aragonés | Alfred E. Neuman |
| 3 | - | comic story | 1 | script: Antonio Prohías; pencils: Antonio Prohías; inks: Antonio Prohías; colors: Carrie Strachan | The Black Spy; The White Spy; The Gray Spy |
| 4 | Senseless in Seattle | comic story | 4 | script: Stan Hart; pencils: Mort Drucker; inks: Mort Drucker | |
| 5 | Romance: Before & After the Economic Slump | comic story | 2 | script: Barry Liebmann; pencils: Peter Bagge; inks: Peter Bagge | |
| 6 | One Beautiful Evening Last May | comic story | 1 | script: Don Martin; pencils: Don Martin; inks: Don Martin | |
| 7 | The Mad Reader's Sex Survey | comic story | 2 | script: Larry Siegel; pencils: Bob Clarke; inks: Bob Clarke | |
| 8 | The Young Man's Guide to Successful Mall Romance | comic story | 2 | script: Jacob Lambert; pencils: Rich Powell; inks: Rich Powell; letters: Rich Powell | |
| 9 | Mad Presents Some Graphic Demonstrations of... When Not to Use Famous "Pick-Up" Lines | comic story | 2 | script: Chris Hart; pencils: Al Jaffee; inks: Al Jaffee | Alfred E. Neuman (cameo); Snow White (at a masquerade party) |
| 10 | A Second-Rate Etiquette Guide to Trailer Trash Dating | comic story | 3 | script: John Caldwell; pencils: John Caldwell; inks: John Caldwell | |
| 11 | Dating a True Crime Fanatic | comic story | 1 | script: Rebekah Brandes; pencils: Gideon Kendall; inks: Gideon Kendall; colors: Gideon Kendall | |
| 12 | The Lighter Side of Summer Romances | comic story | 4 | script: Dave Berg; pencils: Dave Berg; inks: Dave Berg | |
| 13 | The Mad Etiquette Guide for Modern Workplace Romances | comic story | 2 | script: Mike Snider; pencils: Kevin Pope; inks: Kevin Pope | |
| 14 | Sluts in the City | comic story | 5 | script: Josh Gordon; pencils: Mort Drucker; inks: Mort Drucker | Sarah Jessica Parker [as Catty Broadshow]; Kim Cattrall [as Slamantha Johns]; Cynthia Nixon [as Marimba Hopps]; Kristin Davis [as Shallow Yorkie]; Chris Noth [as Mr. Biggie]; David Eigenberg [as Strive]; Kyle MacLachlan [as Tripe]; Brent; Scooter; Hagar the Horrible (cameo); Emilio; James Gandolfini |
| 15 | The Inseparable, Insufferable Couple | comic story | 1 | script: Johnny Sampson; pencils: Johnny Sampson; inks: Johnny Sampson; colors: Johnny Sampson | |
| 16 | The Mad Love Book | comic story | 3 | script: George Hart; pencils: Paul Coker; inks: Paul Coker | |
| 17 | Love Corruption | comic story | 4 | script: Dick DeBartolo; pencils: Angelo Torres; inks: Angelo Torres | |
| 18 | Closer Encounters | comic story | 2 | script: Jon Adams; pencils: Jon Adams; inks: Jon Adams | |
| 19 | A Mad History of Sex | comic story | 6 | script: Larry Siegel; pencils: George Woodbridge; inks: George Woodbridge | |
| 20 | Mad's Maddest Artist Takes a Look at a Fairy Tale | comic story | 1 | script: Don Martin; pencils: Don Martin; inks: Don Martin; colors: Don Martin | |
| 21 | Mad's "Romance-Love-Relationship" Book | comic story | 3 | script: Frank Jacobs; pencils: Paul Coker Jr.; inks: Paul Coker Jr. | |
| 22 | - | comic story | 1 | script: Antonio Prohías; pencils: Antonio Prohías; inks: Antonio Prohías | The Black Spy; The White Spy; The Gray Spy |
| 23 | Things You Don't Want to Hear While Playing Spin the Bottle | text story | 0.5 | script: Kit Lively; pencils: Josh Mecouch; inks: Josh Mecouch; colors: Josh Mecouch | |
| 24 | - | cartoon | 0.25 | script: Scott Nickel; pencils: Scott Nickel; inks: Scott Nickel; colors: Scott Nickel | |
| 25 | - | cartoon | 0.25 | script: Ian Boothby; pencils: Pia Guerra; inks: Pia Guerra | |
| 26 | Who Will Feel It the Most if Taylor and Travis Break Up? | activity | 1 | script: Johnny Sampson; pencils: Johnny Sampson; inks: Johnny Sampson; colors: Johnny Sampson | |