Dear Katherine,

I need some help. I’m 20 years old, I’ve had multiple sexual partners but nothing consistent, and I’ve never been in a relationship. My best sexual encounters are when I don’t care about the girl or whatever is going to happen afterwards. With the last girl I was talking to, I did care. I’m trying with every fiber to not be a dickhead, like I may have treated other girls I’ve had one-night stands/casual sexual encounters with. I don’t think I want a relationship for a while, so what tips can I get to enjoy my 20s, sleep around and not worry about this kind of stuff?

Thank you,

Dear Blake,

It sounds like you’re really traversing two of the most precarious pillars of masculinity: the nice guy who gets trampled on or “friend-zoned”, and the agro “I don’t give a shit” dude who has sex with women he actively doesn’t care about. Fortunately for you there are many facets of masculinity and humanity in between and outside of these bounds.

To help you with your dilemma, I’ve turned to billionaire libertine Sir Richard Branson, whose book Screw It, Let’s Do It has some particularly apt bullet points.

Start by believing you’re not an asshole. Or a clingy pushover. Or anything you don’t want to be. Branson says he always starts by setting himself “huge, apparently unachievable challenges and trying to rise above them.” I suggest you do the same.

What do you want? Do you want to be a good guy and sleep with a lot of women? Make that your organizing principle. I would venture to say that it’s possible to achieve, but you need to define it. While I don’t often think that being a good person fits into a goal-oriented psychology, as you go about your romantic life ask yourself if your actions align with your stated goals.

Let’s address your feeling that the best sexual encounters you’ve had are when you don’t “care about the girl or what happens afterwards”. An undeniable aspect of sex is the potential recklessness at the center of its fullness. Sex, unlike so much else, can operate outside of a moral dimension — and in our puritanical culture, that’s something worth exploring. Some of us are more into this recklessness than others. Simultaneously, having anonymous sex with people you don’t care about can be an avoidance of intimacy. I would suggest that you try divorcing in your mind the “not caring about the girl” from the not caring about “what happens afterwards.” It’s entirely possible to care about what happens to somebody in a moment and not want to see them again after that moment. The first rule of being a playboy is that you appreciate the people you’re with socially and sexually as full humans. Without that you’re just a boy.

You will fail at this. I can almost guarantee it. Your twenties are about messing up and making mistakes. But when you fail—when you find yourself being an asshole or getting called out for being suffocating, don’t give up and give in. Take responsibility for your actions. Apologize if necessary or give the other person space and keep going.

Branson once said the best advice he ever got from his father was to wear a condom. I would suggest you do the same. At baseline, the most respectful thing you can do is not give another person an STD/I. It’s a good practice of self-respect to protect yourself from them as well.

Branson says: “Try to avoid falling out with people. The world is a very small place.” Pretty much everybody I’ve ever had a relationship with I’ve run into again. And again. And again. Most people don’t disappear, even if you want them to. Even if you don’t physically see people again they can and will contribute to your reputation—and that’s something that travels fast and falls apart even faster. Explore ways to help other people out—whether you’re sleeping with them or not.

DO THE RIGHT THING (not just a Spike Lee movie, also a Branson Tip)
I would venture to say that part of what you’re up against is the fact that women have been told that a stable monogamous relationship is something to aspire to because any other configuration will screw them. For a long time that had some social and economic truth to it. Men, meanwhile, have historically been encouraged and supported to pursue multiple partners, wives, marriages etc. Summary: That shit wasn’t fair, and everybody’s still working on it. I relay this to contextualize your question about “being an asshole.” The fact that you are even able to ask how not to be an asshole is the result of your historical privilege. The more you understand that, the less likely you are to be one.

Anyone has the potential to be a “dickhead,” or “a good man.” Search for other, less moral organizing principles of how to be a sexual being that expand your sense of self rather than diminish it. When you’re seeking pleasure don’t forget to seek meaning. You’re off to a great start.


Just the Tips is’s weekly advice column with professional matchmaker Katherine Cooper. Have a question for Katherine about sex, love or dating? Shoot her a note at or follow her @kathkathcoop.