Stop talking about where you went to college.
Always carry cash. Keep some in your front pocket.
Rebel from business casual. Burn your khakis and wear a suit or jeans.
It’s okay to trade the possibility of your 80s and 90s for more guaranteed fun in your 20s and 30s.
The best public restrooms are in hotels: The St. Regis in New York, Claridge’s in London, The Fullerton in Singapore, to name a few.
Never stay out after midnight three nights in a row … unless something really good comes up on the third night.
You will regret your tattoos.
Never date an ex of your friend.
Join Twitter; become your own curator of information.
If riding the bus doesn't incentivize you to improve your station in life, nothing will.
Time is too short to do your own laundry.
When the bartender asks, you should already know what you want to drink.
If you perspire, wear a damn undershirt.
You don’t have to like baseball, but you should understand the concept of what a pitcher’s ERA means. Approach life similarly.
When people don’t invite you to a party, you really shouldn’t go. And sometimes even when you are invited, you shouldn’t go.
People are tired of you being the funny, drunk guy.
When in doubt, always kiss the girl.
Tip more than you should.
You probably use your cell phone too often and at the wrong moments.
Buy expensive sunglasses. Superficial? Yes, but so are the women judging you. And it tells these women you appreciate nice things and are responsible enough not to lose them.
If you want a nice umbrella, bring a shitty one to church.
Do 50 push-ups, sit-ups, and dips before you shower each morning.
Eat brunch with friends at least every other weekend. Leave Rusty and Junior at home.
Be a regular at more than one bar.
Act like you’ve been there before. It doesn’t matter if it’s in the end zone at the Super Bowl or on a private plane.
A glass of wine or two with lunch will not ruin your day.
It’s better if old men cut your hair. Ask for Sammy at the Mandarin Oriental Barbershop in Hong Kong. He can share his experiences of the Japanese occupation, or just give you a copy of Playboy.
Learn how to fly-fish.
No selfies. Aspire to experience photo-worthy moments in the company of a beautiful woman.
Own a handcrafted shotgun. It’s a beautiful thing.
There’s always another level. Just be content knowing that you are still better off than most who have ever lived.
You can get away with a lot more if you're the one buying the drinks.
Ask for a salad instead of fries.
Don’t split a check.
Pretty women who are unaccompanied want you to talk to them.
Cobblers will save your shoes. So will shoe trees.
When a bartender buys you a round, tip double.
The cliché is that having money is about not wasting time. But in reality, money is about facilitating spontaneity.
Find a Times New Roman in the streets and a Wingdings in the sheets. She exists.
Piercings are liabilities in fights.
Do not use an electric razor.
Desserts are for women. Order one and pretend you don’t mind that she’s eating yours.
Buy a tuxedo before you are thirty. Stay that size.
One girlfriend at a time is probably enough.
Your ties should be rolled and placed in a sectioned tie drawer.
Throw parties. But have someone else clean up the next day.
You may only request one song from the DJ.
Measure yourself only against your previous self.
Take more pictures. With a camera.
Place-dropping is worse than name-dropping.
When you admire the work of artists or writers, tell them. And spend money to acquire their work.
Your clothes do not match. They go together.
Yes, of course you have to buy her dinner.
Staying angry is a waste of energy.
Revenge can be a good way of getting over anger.
If she expects the person you are 20% of the time, 100% of the time, then she doesn't want you.
Always bring a bottle of something to the party.
Avoid that “last” whiskey. You’ve probably had enough.
Don’t use the word “closure” or ever expect it in real life. There may still be a mortally wounded Russian mobster roaming the woods of south Jersey, but we’ll never know.
If you are wittier than you are handsome, avoid loud clubs.
Drink outdoors. And during the day. And sometimes by yourself.
Date women outside your social set. You’ll be surprised.
If it’s got velvet ropes and lines, walk away unless you know someone.
You cannot have a love affair with whiskey because whiskey will never love you back.
Feigning unpretentiousness is worse than being pretentious. Cut it out with the vintage Polo and that ’83 Wagoneer in Nantucket.
The New Yorker is not high-brow. Neither is The Economist.
If you believe in evolution, you should know something about how it works.
No-one cares if you are offended, so stop it.
Never take an ex back. She tried to do better and is settling with you.
Eating out alone can be magnificent. Find a place where you can sit at the bar.
Read more. It allows you to borrow someone else’s brain, and will make you more interesting at a dinner party – provided that you don’t initiate conversation with, “So, who are you reading …”
Ignore the boos. They usually come from the cheap seats.
Hookers aren’t cool, and remember, the free ones are a lot more expensive.
Don’t ever say, “it is what it is.”
Start a wine collection for your kids when they are born. Add a few cases every year without telling them. It’ll make a phenomenal gift in twenty years.
Don’t gamble if losing $100 is going to piss you off.
Remember, “rules are for the obedience of fools and the guidance of wise men.”