[Editor’s note: The inimitable Rude Jude Angelini now has a new weekly advice column for TheHundreds.com. The shock jock-turned-memoirist wrote one of Bobby Hundreds’ favorite books of 2014. Now, he’s taking his sharp wit to The Hundreds in a recurring advice column where figures from our community reach out and ask Rude Jude for a helping hand.]

Yo Jude! Should I keep pursuing?

I’m a very shy guy, and am having trouble with women. A couple months ago my friend (knowing about my shyness) decided to hook me up with one of her friends. She showed the friend what I looked like, told her about me, she ended up being on-board (she liked me didn’t care that I was shy) we started talking, getting to know each other but we never met up (my work schedule and her school schedule wasn’t matching up). We were talking here and there for the past couple months until recently. Then one day I sent her a text, she replied back I thought everything was fine, but then a week later I texted her no reply and then the same a week later. I haven’t texted since, what should I do?

Quick sidenote:
She’s used to dating assholes and is not used to nice guys and when her and I were talking, she and my friend admitted she’s a horrible texter gets distracted and won’t always text back but it feels like she wasn’t distracted, it feels like I was just too nice for her.

Signed,
Shy Guy

Aww!!! You’re a shy guy! Well, that’s just cute as hell… if you’re a toddler, hiding behind your grandma’s leg when she takes you to meet the Easter Bunny. But you’re a fucking man now and that’s about as cute on you as walking around with a balloon sucking your thumb.

This shy shit ain’t gonna do you no good in the dating world. It’s too passive. It automatically puts you in this category where you’re not the master of your own destiny. If you’re not being assertive then all you end up with is who chooses you. Fuck that, that ain’t no way to live.

Now don’t get me wrong, I’ve seen this shy shit work. I got a buddy who’s all adorable with a messy haircut, looking like he works at American Apparel. He just posts up at the bar with a sheepish grin and chicks throw pussy at him. I know another cat who plays shy and tells all his platonic girlfriends he can’t meet a nice girl. And then they cosign him with their girlfriends. And he hits these chicks with the, “Oh, I wonder what a vagina feels like, I’m such a nice guy. Can’t we just cuddle?” And they give him the pussy because he’s non-threatening and then he blows them off. But that’s not really shy, that’s game. They running shy game.

“YOU’RE WORRIED ABOUT MISSING THE FREE-THROWS INSTEAD OF CONCENTRATING ON MAKING THEM.”

You? You’re just shy. You’re just choking… You’re nervous about interactions with chicks, busy worrying about what to say in a conversation instead of just listening and letting it come naturally. You’re worried about missing the free-throws instead of concentrating on making them. I know this – because I was you. Nice sensitive guy, probably wants to avoid rejection so he doesn’t put himself out there.

Here’s a secret: Getting shot down by a chick hurts, but it don’t hurt as bad as watching other motherfuckers have fun while you’re sitting on the sidelines. And you know what? The more you get shot down, the less it hurts. So you gotta get out there, holler at chicks, develop some game, see what works, discard what doesn’t. Study other cats, see what they do, copy that shit. Fake it till you make it. Don’t take this shit so seriously, have fun.

Shit – holler at some ugly broads, get you some pussy.

Chicks can tell when you’re not getting pussy, they smell the desperation. And on the flip side, they can tell when you are, but they can’t tell the caliber.

Now onto your current situation:

DEAD IT.

It’s done. You’re not ready for this one yet. You’re already way to emotionally invested and you’ve never seen her.

Real talk: You were prolly a fucking sympathy case. She was prolly complaining to your girl about getting dogged by some asshole. And your friend suggests you, this really nice guy who just needs a chance. And they’re halfway into their second bottle of chardonnay. And she’s like, “Fuck it, what the hell. I need a nice guy.”

But that’s not what she wants, ’cause if that was the case, she wouldn’t keep dating assholes. The same way if she really wanted to see you, she would’ve seen you by now. But she didn’t. In fact she’s probably giving the dude that was dogging her morning-head as I type this.

It feels to me like you’re thinking about her more than she’s thinking about you and where you’re at in knowing how to deal with women... It’s just a little too much for you now. Work on talking to chicks around you, face to face. Hit on some women, pull a few, get dissed and maybe a couple years from now you can crack this chick you’ve been texting.

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Got questions for Rude Jude? Email YoJude@TheHundreds.com.