Sam and Milo are best friends who work at a Chicago commercial production agency. Sam fixes up Milo on a blind date with an acquaintance named Robyn, and it turns into a disaster. The disaster continues when the two suddenly discover that Robyn has been hired as their new boss.
| Title | Air Date | Duration | ||
|---|---|---|---|---|
| Season 1 | Episode 1 | When Co-Workers Attack | 1998-04-06 | 30 min |
| Season 1 | Episode 2 | Milo Does the Darndest Things | 1998-04-13 | 30 min |
| Season 1 | Episode 3 | Guess Who Else Is Coming to Dinner? | 1998-04-20 | 30 min |
| Season 1 | Episode 4 | Sam I Am | 1998-04-27 | 30 min |
| Season 1 | Episode 5 | My Best Fling's Wedding | 1998-05-04 | 30 min |
| Season 1 | Episode 6 | Raiders of the Lost Watch | 1998-05-11 | 30 min |
| Season 1 | Episode 7 | Chasing Sammy | 1998-05-18 | 30 min |
| Season 1 | Episode 8 | The No Joy Bad Luck Club | 1998-07-31 | 30 min |
| Season 1 | Episode 9 | Bring in Da Milo, Bring in Da Robyn | 1998-08-07 | 30 min |
| Season 1 | Episode 10 | The Date After | 1998-08-14 | 30 min |
| Season 2 | Episode 1 | Fix Me Up, Tie Me Down | 1998-09-11 | 30 min |
| Season 2 | Episode 2 | The Doctor Is In | 1998-09-18 | 30 min |
| Season 2 | Episode 3 | There's Something About Rhonda | 1998-09-25 | 30 min |
| Season 2 | Episode 4 | The Wedding Zinger | 1998-10-02 | 30 min |
| Season 2 | Episode 5 | Midnight Milo | 1998-10-09 | 30 min |
| Season 2 | Episode 6 | Saving Milo's Privates | 1998-10-16 | 30 min |
| Season 2 | Episode 7 | Last Three Temptations of Robyn Buckley | 1998-10-16 | 30 min |
| Production | Benny Medina | Producer |
| Production | Greg Garcia | Producer |