Made for Playboy's "Inside Out" TV show, the short follows an eccentric dweeb who, after noticing an attractive woman sucking on a popsicle, tries following her. However tragedy keeps befalling him at every turn, leading to many wacky situations as he pursues the lady.
| Actor | Role |
|---|---|
 Alex WinterDweeb | Dweeb |
| JJennifer MoffetWoman with Popsicle | Woman with Popsicle |
 Lee ArenbergLarry the Head | Larry the Head |
 Tom SternVarious Characters | Various Characters |