Advice

On giving lessons.

I have been with my boyfriend for 2 years now. He is extremely articulate, worldly, shares my strange sense of humor, love of illicit substances, outstandingly compatable tastes in literature/art/music, is an amazing artist on his way to grad school, kind and gentle, treats me like a princess, etc, and a well endowed, adorable Jewish boy. But he doesn’t know how to use it! Or his tongue. Or hands. I CAN NOT let this one go, out of the question, but how should I handle this?

This really isn’t a big deal. Man’s ability to adapt and learn is remarkable. All you have to do is train him. Use positive reinforcement, but give him explicit lessons in exactly how you want your lovin’.

Soften the initial blow by avoiding phrases like, “you don’t know what you’re doing.” Instead, give him a lot of not-his-fault style mantra such as, “no one ever taught you this.”

To protect his male ego, take on some of the blame yourself. After all, you’ve been with him for two years and you’ve never done anything about it until now.

Don’t be bashful. Don’t be apologetic. Demand he get it right. You can make it playful, but get him on a sex regimen where he doesn’t get gold stars unless you get orgasms.

Trust me, it’s worth the effort. In a few short months of increasingly pleasant exercises, you’ll have your very own customized lover boy.

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Advice

On plastic surgery.

I have been thinking about getting a boob job for a few years… what’s your opinion on plastic surgery?

As long as you’re making an emotionally healthy decision and not putting it on a credit card, I’m all for plastic surgery.

Be sure to do your research on all the various procedures and the doctors in your area. Shop around. Pick your three favorite board certified surgeons and schedule consultations with each one. Never settle when it comes to choosing the right doctor.

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Advice

On classic hook-up errors.

I hooked up with my best guy friend last night because I was wasted and the guy I was seeing this summer and who I share a pretty special bond with found out… is that bad? It’s been a month since I’ve seen both of them cause of university and I feel like I fucked up hard.

Yeah, that’s bad. Ruining your favorite romantic and a platonic relationships with one drunken hook-up definitely qualifies as fucking up hard.

If you want to keep them both, take full responsibility for your actions and apologize. The silver lining here is that you’ve got all the makings of an awkward college threesome.

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Advice

On creative deflowering

I’m sixteen and I kind of want to lose my virginity just to get it over with. I don’t feel pressured to lose it, but I just want to… bad idea?

Nope, not a bad idea. You only get one first time, though. Instead of just getting it over with, I suggest you get creative.

Have you ever considered auctioning off your virginity for charity?

Seriously, why not? I’m sure there are tons of wealthy perverts with a virgin fetish who’d pay big bucks to pop your teenage cherry for charity. No joke.

Start a website called cherryforcharity.com. Put that shit on eBay. Open the bidding at $100,000.

Don’t worry, it’s not prostitution if the guy writes a check directly to a nonprofit of your choosing. Just double-check that the age of consent in your neighborhood is sixteen, and it’s all perfectly legal.

In a world that’s running out of original ways to generate fifteen minutes of fame, I guarantee this would start a shit storm of publicity. Not only is this clever and controversial, but you’d piss off all the right people and raise some major awareness for a worthy cause.

You’d be making the world a better place with your pussy. How many of us ever get to do that?

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Advice

On being unfulfilled.

only 17 years old and i can already anticipate that my life is only going to get worse. i know that there are moments in life that are worth living for, but to me it all seems so pointless. love doesn’t last forever, kids grow up into brats, and you always end up feeling unfulfilled. is there a way to escape from it at all?

Love doesn’t last forever? Neither do orgasms, princess. I guess you should just go ahead and kill yourself. Seriously, it’d be one less whiny teenage cunt who thinks she’s entitled to fulfillment.

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Advice

On apathy.

What do you think the reason behind today’s youth using apathy as their greatest way to become cool/greatest defense mechanism is?

I don’t accept the premise of your question. If the cool kids in your world are apathetic, you’ve chosen poorly. I suggest you try idolizing a fresh batch of hipsters.

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Advice

On listening to your gut.

Every guy I have talked to within the last 5 months has brought up fucking before our first kiss. I find myself in a similar situation right now, and I actually kind of like this guy, and he has been a real gentleman up until this point. Well, he is still being sort of a gentleman, as much of a gentleman as someone could be when talking about plowing you.

Should I ditch him and wait for someone else to come along or should I stick around to see if he is at all different? I have two gut feelings and I am not sure which one to rely on.

I am looking for a relationship or someone I can date, not a fuck buddy.

Let him plow you, but tell him to watch out for that stick in your ass. Hell, if you’re lucky he’ll know how to work that stick while using your ponytail as a handle. You could use a little loosening up.

I can’t stand it when people keep lists of esoteric, unrealistic rules wherein “a gentleman doesn’t do this,” and “a lady doesn’t do that.”

So what if he brought up fucking before your first kiss? Was he funny? Was he clever? Was he sexy? If so, who cares if he didn’t live up to some silly bit of etiquette. Ignore your rules and focus on the situation.

You only have one gut feeling by the way — it’s the one telling you that you actually like this guy. The other feeling belongs to some external source — most likely your mother — that has you convinced how the world “should” be instead of how the world actually is.

Learn to tell the difference between that external source and your own instincts, and you’ll be a much happier person.

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Advice

On getting head in a van.

A friend and I have known each other for quite some time now, and we always smoke together, go to shows together, ecetera.

Last night we were down in LA at a show. Halfway through, he took me to his friend’s van and went down on me right then and there.

I don’t know what to say to him at this point, because he does have a girlfriend (who is only fourteen), and according to him, he loves her and wants to “marry” her.

Do I keep hanging out with him and ignore our little incounter, or just stay away from him altogether?

Probably a good idea to stay away from any dude with a fourteen year old girlfriend who goes down on you in a van without any warning.

Fourteen? No warning? A van? That’s a trifecta of creepy.

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Advice

On cocaine chic.

are you like skinny as fuck cause of all that coke?

I wish. Besides, that whole cocaine chic thing is a myth. You have to be a straight-up crackhead for that shit to markedly effect your weight. A fuck ton of skinny chicks do blow, but correlation doesn’t equal causation.

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Advice

On not cheating

How do you feel about cheating? Have you ever cheated on the person you were with?

I don’t cheat. Then again, being true and faithful in your relationship has no inherent connection to how many sexual partners you have.

If you’re interested in what I’ve written on monogamy and fidelity, click here.

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