The death of Sam's old friend and former Red Sox teammate inspires Sam and Matt's journey to the roof of Fenway Park. Sarah hosts a dinner party but is upset when Jared brings a date.
| Name | Type | Role | |
|---|---|---|---|
| Jimmy Aleck | Writer | ||
| Jim Keily | Writer | ||
| Jennifer Kelly Tisdale | Guest Star | ||
| Vic Polizos | Guest Star | ||
| Courtney Peldon | Guest Star | ||
| Lee Shallat Chemel | Director |