It would be nice to have been born good-looking, but even if you weren’t, you can relax. Women don’t care all that much if you’re good-looking. But they do care if you’re cool, so you can’t totally relax. Here’s the paradox: in order to be cool, you sort of have to relax. Cool is all about contradictions like this. Do this, but not always. Do that, but not for that reason. Reading this article, you’ll be forced to think about being cool, which isn’t that cool. So read it in the privacy of your home. But read it. Because if you understand coolness, then it becomes possible to cultivate it.

Cool is about being who you are…

You want to impart to everyone – especially to any woman who might be sizing you up as a potential hook-up – that hey, being you is pretty good, maybe even fun. It’s a simple concept that’s hard to fake.

Thank God, then, that there are no rules pertaining to what women find cool. There are cool loud guys and cool quiet guys. Cool guys listen to jazz and electronica and rock and pop, and so do uncool guys. (No one who listens to jam bands is cool.)

You can wear baggy tracksuits and funky hats and be sort of weird looking but still be cool. Oh, sorry, that’s only if you’re Jay-Z. The point is that just about anything goes, as long as you do it with confidence and without looking to see who approves.

…but it’s not about announcing who you are. When you advertise yourself as just about anything – a star athlete, a type-A personality, a stand-up guy – you’re suggesting that your demeanour won’t speak for itself. Instead of telling her you got a fat bonus cheque, take her out to dinner. Resist relaying the details of your gruelling hour-long workout routine, and just fit into your damn pants. Never, ever, use the phrase “I’m the kind of guy who…” If it’s really true, she’ll find out.

Cool guys refuse to engage in activities that make them feel silly…

You know that moment at a concert when the performers try to force everyone in the audience to clap or sing along? The impulse that tells you that you might die of shame if you do it is a good one. When it comes to earning a woman’s respect and admiration, you are nothing without dignity. It’s better to be a killjoy than a lemming.

…unless mothers or kids are involved. If it’s your nephew’s bar mitzvah and your mother wants you to dance the hora, you’re going to join the circle and spin. And you’re going to like it. Sometimes being cool means knowing it’s not just about you.

Cool guys run their own lives…

A cool guy has reasonable control over the way he makes his living, and if he doesn’t have that control, he should be taking concrete steps to change it. A cool guy values his family but doesn’t live in service to them (unless they’re ill). A cool guy isn’t always asking everyone what his next move should be, because he should always have his next move planned.

…but they accept advice when appropriate. Yes, a renegade spirit is an important part of coolness. But don’t make it your god. There are times when the beat of your own drummer should be drowned out by the counsel of good friends.

You will recognise your good friends by their excellent suggestions, such as, “That girl you’re dating who has five kids by four different fathers probably doesn’t have time to convert to Roman Catholicism.”

You will honour those friends with your gratitude, humility and compliance. “Whatever, dude, it’s my life and I’ve done a pretty good job this far without you” sounds great in the movies, but only because that guy’s going to either end up being right or look really hot being wrong. You, on the other hand, are just going to look like you, only bummed, poor, divorced or dead. “Cool” and “pig-headed” are not synonyms.

Cool guys are cheerful…

There’s a reason the brooding anti-hero became popular, and that’s because men look good smoking and sulking onscreen. They do not look good smoking and sulking in real life. So smile frequently. If you have to complain, make sure your complaint takes the form of an amusing and preferably self-deprecating anecdote.

**…but not aggressively cheerful. **The only thing less cool than the perpetually miserable guy is the guy who is always telling you how great everything is. He may even believe that if he acts happy, he will become happy. And he may achieve this, in a head-bobbing-Chihuahua-dashboard- ornament sort of way. But he will never be cool, because at the end of the day being cool is about having people walk away from you thinking you know something they don’t know, that you have secrets to which they may be privy should they spend a little time in your company.

Cool guys are generous…

Of all the cool gestures you can make, few equal that slight lift of the chin to the waiter, coupled with the hand sliding into the breast pocket. Everyone – not just women – loves the guy who picks up the tab, so do it when you can. But, more important, be the guy who lugs the sleeper couch up five flights of stairs, feeds Snowball and Trisket while their owners are in Zanzibar, or lets drunk people crash on his couch. The generous guy is an object of wonder: he must have his game all figured out if he’s got the time to do this.

…but they have the right motives. You have to mean it. Don’t take a girl to the airport hoping she’ll come back not only with a tan but suddenly in love with you. When you do nice things for people because you’re looking for a return on your investment, you will find yourself disappointed. And accumulated disappointment leads to bitterness, and there is nothing – nothing – less cool than that. Take care of your own needs. Do nice things only for people who deserve it. And the next time you’re at a party and the girl of your dreams walks in, let someone else go out for more ice.