Have you ever met someone who tries WAY too hard to be funny? So hard, in fact, that they aren't funny at all? This is the person who obviously sits at home and thinks about funny things to say. There's no way at all that what they say just rolls off their tongue. It's too perfect, too rehearsed.
This person drives me crazy. Thankfully she's not a friend. I couldn't be friends with her. I'm too nice to tell anyone that they're not funny, so I'd have to fake-laugh all the time, and that would get old quick. Way too much work. She also tries too hard to reference people/places/etc. so that she seems to be a whole lot smarter and 'cool' than she really is. And she's one of those people that no matter what happens in your life, it or something worse has happened to her. She barely lets you get your story out before she's swung full force into hers. That is so awful.
I can put up with little character flaws, no problem. Most of them are cute and endearing. In fact, I've got quite a few myself, I'm sure (I try not to think about that). But when your flaw takes over any other personality you might have, that's just too much for me. I can't handle it. I can't even pretend to handle it.
On a side note, this guy is a real winner. Anyone who willingly asks for more jail time is beyond the realm of help. He'll get torn apart in prison. I'd be surprised if he survives the full 33 years.