So what if you can see the darker side of me

I've had an ongoing struggle with that 18 yr old guy from work. He tells me I'm the only person he can stand to be around. He says, "I'm an asshole, but this is the NICE me at work. I'm worse when I'm not here."

I tell him that he's an angry loner. And he says, "What's wrong with Angry Loners?"

And I say, "Well... they're angry. And they're loners..."

One night he pulled out a light-up keychain and said, "Check this thing out. It's cool."

I said, "Where did you get that?"

He said, "Walmart. Lastnight. At 3am."

I said, "Why were you at Walmart at 3 am?"

He said, "Because my life sucks. There is nothing to do." Later he explained it this way, "I'm 18 and I can't do anything except go to strip clubs." He is actually trying to spend his time doing worthwhile things but he can't figure anything out in that falls in that category. He doesn't want to spend all his time drinking like his friends and he already quit playing World of Warcraft.

I told him, "You really need to ask that girl out from the restaurant we go to for lunch."

Did I mention he hates girls? And kids? And pretty much everyone? But he especially hates girls. And kids. He sees them as financial death and endless nagging. It's hard to pose an argument against that. But he seems to be incapable of seeing an upside to hanging out with girls.

He asked, "Why would I want to do that?"

I said, "I don't know. Because you hang out at Walmart at 3 am FOR FUN. If you asked her out, she might at least hang out at Walmart with you."

I told him, "You two kind of look alike and they say people are often attracted to other people who have similar traits." I said, "You're both tall and skinny, you have the same kind of nose, you both seem to like wearing baseball hats..." (the girl has to wear a work hat)

He said, "We both have the same size of boobs."

I said, "So what about boobs?"

He said, "If a girl doesn't have boobs its like having sex with a man."

I said, "Don't worry about boobs. At some point in time, EVERY girl asks her boyfriend if he likes her boob-size. When she asks you that, you just say HERE ARE SOME PAMPHLETS YOU CAN READ ABOUT BREAST AUGMENTATION."

I told him that having a cool personality is much more important than boobs. He was just using boobs as an excuse. And I knew I was breaking through his shell when he asked me how much boob surgery costs. I told him that he should just ask her if she has seen "Clerks II" (one of his favorite movies) and if the answer was YES then he should ask her out.

But then he sprang back at me... "Why would people be attracted themselves? Would YOU want to have sex with someone who looked just like you?"

And I reminded him about that "Silence of the Lambs/Clerks II" line:

"I'd F*** me. I'd F*** me hard."

But then I told him that my features are much too masculine for me to ever pitch woo to my own twin.

Anyway. I'm still trying to get him to ask a girl out. So he won't be so angry. And alone.