1) Measure yourself only against your previous self.
2) Never cancel dinner plans with a woman by text message.
3) Ignore the boos. They usually come from the cheap seats.
4) You don’t have to keep every secret, just the important ones.
5) If you’re staying more than one night, unpack.
6) A suntan is not bought, it’s earned, and preferably near an ocean, pool, or on a golf course.
7) Place-dropping is worse than-name dropping.
8) Don’t fill up on bread.
9) You don’t have to like baseball, but you should understand the concept of what a pitcher’s ERA means. Approach life similarly.
10) A glass of wine or two with lunch will not ruin your day.
11) Appreciate your parents. When they die, you become an orphan.
12) “Remember when” is the lowest form of conversation.
13) It’s okay to forgive, as long as you don’t forget.
14) Never make a scene. After the age of 22, this also applies when you’re drinking.
15) Buy a tuxedo before you are thirty. Stay that size.
16) If you wear cologne, no one should smell it from 5 feet away or 5 minutes after you’ve left.
17) When giving a toast, short and sweet is always best.
18) If you are wittier than you are handsome, avoid loud clubs.
19) Know when to ignore the camera.
20) Never take an ex back. She tried to do better and is settling with you.
21) Invest in great luggage.
22) Always carry cash.
23) Suck it up every now and then, especially for your family.
24) Never be the last one in the pool.
25) Don’t stare.
27) Stand up to bullies. You’ll only have to do it once.
28) Admit it when you’re wrong, and forgive yourself for your mistakes.
29) Take more pictures. With a camera.
30) If you offer to help, don’t quit until the job is done.
31) Know at least one good joke.
32) There’s always another level. Just be content knowing that you are still better off than most who have ever lived.
33) When you marry someone, remember you marry their entire family.
34) It’s okay to go to the movies by yourself.
35) If you don’t understand, ask before it’s too late.
36) Yes, of course you have to buy her dinner.
37) Never ask the same question twice.
38) Be kind. Life is hard enough as it is.
39) Know your way around a kitchen.
40) Set Goals. Write them down.
41) Stop talking about where you went to college.
42) Rebel from business casual. Burn your khakis and wear a suit or jeans.
43) It’s okay to trade the possibility of your 80s and 90s for more guaranteed fun in your 20s and 30s.
44) Never park in front of a bar.
45) Play competitive sports for as long as you can.
46) Never date an ex of your friend.
47) If riding the bus doesn’t incentivize you to improve your station in life, nothing will.
48) When the bartender asks, you should already know what you want to drink.
49) If you perspire, wear an undershirt.
50) Never stay out after midnight three nights in a row unless something really good comes up on the third night.
51) 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.
52) People get tired of you being the funny, drunk guy.
53) When in doubt, always kiss the girl.
54) Tip more than you should.
55) Always buy good shoes, tires, and sheets.
56) Put your cell phone away. You probably use it too often and at the wrong moments.
57) Eating out alone can be magnificent. Find a place where you can sit at the bar.
58) Do 50 push-ups, sit-ups, and dips before you shower each morning.
59) Eat brunch with friends at least every other weekend.
60) Be a regular at more than one bar.
61) Value a handful of truly close friends over a hundred acquaintances.
62) It’s better if old men cut your hair.
63) Learn how to fly-fish.
64) No selfies. Aspire to experience photo-worthy moments in the company of a wonderful companion.
65) Own a handcrafted shotgun. It’s a beautiful thing.
66) Don’t split a check.
67) If you come from money, embrace it. We live in a world that rewards intelligence, creativity, and risk-taking. Be proud that your parents aren’t lazy dolts.
68) When a bartender buys you a round, tip double.
69) The cliche is that having money is about not wasting time. But in reality, money is about facilitating spontaneity.
70) Be spontaneous.
71) Do not use an electric razor.
72) Desserts are for women. Order one and pretend you don’t mind that she’s eating yours.
73) One girlfriend at a time is probably enough.
74) Your ties should be rolled and placed in a sectioned tie drawer.
75) Throw parties. But have someone else clean up the next day.
76) Buy expensive sunglasses.
77) You may only request one song from the DJ.
78) Remember: You die twice, once when you stop breathing, and again when somebody mentions your name for the last time.
79) When you admire the work of artists or writers, tell them. And spend money to acquire their work.
80) Your clothes do not match. They go together.
81) Staying angry is a waste of energy.
82) Revenge can be a good way of getting over anger.
83) If she expects the person you are 20% of the time, 100% of the time, then she doesn’t want you.
84) Always bring a bottle of something to the party.
85) Avoid that “last” whiskey. You’ve probably had enough.
86) Don’t use the word “closure” or ever expect it in real life.
87) Drink outdoors. And during the day. And sometimes by yourself.
88) Don’t linger in the doorway, in or out.
89) Date women outside your social set. You’ll be surprised.
90) If it’s got velvet ropes and lines, walk away unless you know someone.
91) You cannot have a love affair with whiskey because whiskey will never love you back.
92) The New Yorker is not high-brow. Neither is The Economist.
93) No-one cares if you are offended, so stop it.
94) Hookers aren’t cool, but remember, the free ones are a lot more expensive.
95) Don’t ever say, “it is what it is.”
96) Act like you’ve been there before.
97) Don’t gamble any amount of money that will piss you off if you lose.
98) Give up the dad bod. You’re not Leonardo DiCaprio.
99) Remember: Rules are for the obedience of fools and the guidance of wise men.
100) You can get away with a lot more if you’re the one buying the drinks.