Go to pawn shop and talk with Mel. He drinks too much cola. Go to Matt's apartment and use laminated card with the door.
Take Matt's picture from the table. Leave the place. There is Kramer outside, so go to the kitchen and exit by the window.
Talk with Ned and Ted. Take a baseball from the thief's box. Use it with Ned. Take another ball and again use it with Ned. After then you can talk with Ned about the taser. You will get it. One more time take a ball and give it to Ned.
When Ned and Ted will be busy (high fives), use taser with Ned (pick a moment where their hands are connected). If you do wrong, you need to take a ball and do the trick again. When they fall down, leave the alley.
Go to pawn shop, show Mel Matt's photo. You will find out that Matt already bought a gun (Magnu-Matic 9000).
Go to Randal's apartment. Read the note, go on the roof and talk with friend. No matter what you choose, the ending could be only one.
For ending the fifth chapter you'll unlock the achievement 'Day 6' (on the beginning of next chapter).