The goal of the puzzle is to learn the names of Jack's friends. First, identify the things in the pictures:
| halyard | pan |
| Everest | bale |
| Saratoga | gram |
| salad | robe |
| timbale | nut |
| calzone | yard |
| Erinyes | Shaw |
| western | qi |
| anagram (of "The Matrix") | el |
| hazelnut | rest |
| territory | zone |
| wardrobe | Yes (cover of "90125") |
| sampan | tern |
| nickel | ad |
| Iraqi | Tory |
| rickshaw | toga |
The friends can be put into three loops, each one starting with Jack's best, second-best, or third-best friend. The loops are arranged such that, if you write the name of Jack's friend and the thing they have to their left (i.e. to our right as we face them), you get the name of the thing to the right of Jack's next friend. So for instance, Jack's best friend is Sam, and to his left is a pan; the next person in the chain has a sampan to their right. The chains are:
| Item #1 | Name | Item #2 |
|---|---|---|
| halyard | Sam | pan |
| sampan | Wes | tern |
| western | Ira | qi |
| Iraqi | Terri | Tory |
| territory | Cal | zone |
| calzone | Hal | yard |
| Everest | Tim | bale |
| timbale | Hazel | nut |
| hazelnut | Eve | rest |
| Saratoga | Ana | gram |
| anagram | Nick | el |
| nickel | Sal | ad |
| salad | Ward | robe |
| wardrobe | Erin | Yes |
| Erinyes | Rick | Shaw |
| rickshaw | Sara | toga |
Reading the first letters of the names of Jack's friends (starting with his best, then second-best, then third-best) gives the answer: SWITCH THE ANSWERS.