Prerequisites: Max out Dean's level 2 friendship
Reward: None
Unlocks: Dean level 3 friendship
Your relationship with Dean is a little better now that you've helped him with his eating problems, and you can move things even deeper into friendship territory if you wish. You can track Dean down on most days by visiting either his home, in the north of Moonbury, or the Police Department, just south of your home. Dean likes to mess around, though, so don't expect him to spend too much time at the Police Department. You may need to call in your dog to find him if he's not at home or work.
Max out the second level of your relationship with Dean and a notice will appear on the Bulletin Boards of Moonbury. It's from Osman, the chief of police, and he's looking for volunteers to help out part-time. You can speak to Osman between 8:00 and 22:00 at the Police Department, any day of the week.
Rather than a recruitment drive you'll come upon Osman chewing out Dean and his brother Derrek, specifically yelling at Dean for losing some files. Dean will mope off and quit, though a pep talk will get things back on track. Your relationship with Dean will improve to the third level as a result.