Even if he wasn't an asshole, Chris will never get a girlfriend. This is something Chris needs to accept if he's ever going to be happy.
After that, all Chris has to do is endure Barb a little while longer and he can spend the rest of his life playing video games and relaxing with no responsibilities... but only if he can stop doing stupid shit like wasting his money, getting arrested, and burning his house down.
I wouldn't take that deal, because today, $1,000,000 is not really a game changer as far as someone's life goes. Being a millionare today means much less than it did 60 to 70 years ago.
Only if you have expensive tastes, or if you want to start a large business. For most people in the US, a million dollars is worth around 20 years of work, assuming it's not taxed. For Chris, it's worth almost 1000 tugboats.