Fun-Sized Advice

On fun-sized advice

Is it normal for a person to keep a detailed record of every single person they ever hooked up with? With pictures and attractiveness ratings.
No. No, no, no. Nooo.

How do you deal with a relationship that has ended but the person just throws shit at you because their perception is that you abandoned them?

If you still have to deal with the relationship, then it hasn’t really ended, now has it?

What are your thoughts on the phrase: “Why buy the cow when you can get the milk for free?”

It’s a tired cliché referencing antiquated and irrelevant notions of virginity and marriage. You can safely ignore anyone who mumbles that kind of stupidity.

What do you do when you realize you have become what you fear most?

Either embrace what you’ve become or change.

Changing my relationship status on Facebook after a breakup feels stupid and insignificant, but it also somehow feels necessary for closure… I can’t figure out why.

Your Facebook profile is an expression of your public identity, and while publishing your relationship status is inherently stupid and insignificant, it doesn’t change the fact that making the breakup public also makes it official. Thus, you feel a sense of closure.

What does it take to have a woman like you, if only for a little while?

I’m not a possession, dude. No one gets to have me.

Why do women hate other women?

It’s one of the ugly side effects of the patriarchy.

My girl thinks her intense, sometimes needy love for me is getting in the way of her sexual desire for me. Do people have trouble fucking the ones that they love? Is that a thing?

It’s not a healthy thing, but yeah, it’s a thing. The two of you need to spend some time openly communicating about this. You’ve got to get to the root cause of this issue, or it’s bound to end in disaster.

How do I tell the girl I like that I’m interested in her without being awkward?

What’s your reason for telling her that you’re interested? Are you trying to date her? Fuck her? What are your intentions? Has she done anything to lead you to believe that she might have feelings for you too? Hell, is she even available? If you don’t have clear and immediate answers to all of these questions, there’s no hope of you not making it awkward.

How do I know if my girlfriend loves me?

Dude, she’ll tell you with her actions and her words exactly how she feels about you. If you’re not paying attention to what she’s telling you, that’s a minor communication issue you can fix by being present in the relationship. If you don’t believe what she’s telling you, that’s a major trust issue you need to address or it will ruin everything.

I’m caucasian and attracted to a brilliant, attractive Asian woman. There’s long-term potential, but when I think about having kids, everything stops; I want kids that look about half like me. Is this some strain of racism? Pride? If not, what the hell is it? And how do I overcome it? Thanks.

Your kids will still look like you, dipshit. That’s how it works. And yeah, for the record, your reaction is good old fashioned racism with a little dash of narcissism thrown in for good measure. Overcome it by pulling your head out of your ass.

(Check out my latest fun-sized advice over at Playboy, and fellas, feel free to send me your questions at


On goal-oriented dating

I’m in my last year at a good university, enjoying life and getting excited about heading out into the professional world. My biggest insecurity is that I’ve never had a relationship that’s lasted longer than a month. In high school, I was a late bloomer in the dating scene and never even hooked up with someone until the summer before Senior year. Most of my “relationships” (if you want to call them that) have been with girls whose company I enjoy but the chemistry just never seems right. I just can’t seem to find the right girl that I’m both attracted to and has a personality that matches mine. I’m an attractive, social guy, and I don’t put out the desperate vibe – I feel like it’s just circumstance that I haven’t found anyone. But it’s gotten to the point that it really bothers me. I feel like college is a time when I am surrounded by people my own age and of similar intelligence – if I graduate without having had a single meaningful relationship, I’m going to be pretty unhappy. Am I being overly analytical? Should I be less picky?

You don’t need to be less picky. You need to be in less of a hurry. Your problem isn’t that you’re being overly analytical. It’s that you’ve got a ridiculous master plan for your life that includes charts and graphs and a timetable.

I know your type. There’s a voice in the back of your head constantly reminding you that you’re supposed to be married with 2.5 kids and a golden retriever by the time you’re in your mid-thirties. This voice says you’re supposed to date around for a few years before you find the perfect girl and settle down. It says you’re supposed to be in a stable, long-term relationship for a couple years before you get married, and it says you’re supposed to be married for a little while before you start having kids.

This voice in the back of your head (which sounds suspiciously like your mother) has already done the math, and quite frankly, it’s a little disappointed that you didn’t find your future wife during college. Well, guess what, skipper? You need to tell that voice to shut the fuck up, or you’re gonna end up leading a miserable life.

You’re wrong about what will make you unhappy. It isn’t the fact that you might graduate without having had a single meaningful relationship. It’s that you’re blind to the fact that regardless how long they’ve lasted, all of your relationships have been meaningful.

Every random hookup, every super cool chick you weren’t really attracted to, every potential girlfriend that fizzled after the third date — all of them count as meaningful relationships, especially during your college years.

Your single biggest mistake is that you think you have to find the right girl and spend a predetermined amount of time in a relationship before it counts as meaningful. (I’m guessing with you, it’s probably three months.)

Do yourself a huge favor and throw the timetable and your “right girl” checklist out the window. Stop being so damned goal-oriented with your dating. Come on, man. You’re in your early twenties. Smell some fucking roses already.

(Check out my latest column over at Playboy, and fellas, feel free to send me your questions at

Best-Of Advice

On nice guy syndrome

I’m a 21 year old guy with one more semester of college left. If there was a textbook of “nice slightly geeky guy,” it’d have my picture there. I’m not fat, I’m not pimply, but I’m not cut or super-hot either… just a slightly above-average looking guy who knows how to treat a girl.

All of that introduces my question: why is it that I always get thrown into the friend zone? To clarify, I get put into the “gay best friend” zone. I’m straight as the day is long, but I’m the one who gets to hear about new shoes, shopping, cute boys, shitty boys, assholes who stood them up… you get the drift.

Is it because I listen too much? Am I too nice? Should I not offer a shoulder to cry on, tell her the shoes are cute (when they are), or that the dude she’s dating is a douche who’s probably fucking someone else too?

Can you help me? I’m asking because there’s a gorgeous, intelligent girl I’d usually say is out of my league that has expressed lots of interest, and I don’t want her to turn me into another “gay best friend” style friend, where I get to hear about her day, her shoes, and her boy problems.


Ugh. Nothing rolls my eyes into the back of my head faster than a “nice guy” who whines about being in the friend zone, and quite frankly, if it weren’t my job to try and smack some sense into you, I’d tell you to go fuck yourself for the ignorant “gay best friend” remarks. (Not cool, dude.)

Let’s be clear, you are not a nice guy. You are actually a magnificent douchebag with a raging case of Nice Guy Syndrome. (Yep, it’s a thing. Look it up.)

While we’re at it, let’s be clear about something else. You don’t know how to treat a girl. You say you do, but you don’t have the slightest fucking clue. If you really knew how to treat a girl, you wouldn’t bitch about listening too much, and you wouldn’t act like a shoulder to cry on is only something to offer if it’s in furtherance of getting you laid.

That kind of thinking is glaring evidence of the underlying issue with guys like you. You don’t actually respect women. You pretend like you do, and you may even believe that you do, but it’s not real.

It’s outrageous and downright insulting that you think a girl has the ability to turn you into a “gay best friend.” You’re doing that to yourself, because you aren’t really being a friend in the first place. You’re just acting like one with the ridiculous expectation that platonic behavior on your part might somehow transmogrify into romantic behavior on her part.

Sorry, but it doesn’t work that way. Platonic relationships are different than romantic ones. They begin differently, they progress differently, and they sure as hell end differently. You better cozy up to that fact pretty quick, because you simply cannot continue to behave like this with the new relationship. If you want a romantic relationship, you have to be emotionally honest from the get go.

You have to put yourself out there, and if she rejects you as a potential romantic partner, you have to move on without thinking platonic behavior will eventually entitle you to something romantic.

(Check out my latest column over at Playboy.)