I was recently waiting for the bus.
A young woman came up to me. “Excuse me,” she said.
I turned to her. “Yes?”
“You look really nice,” she said. “Have a nice day!”
And she walked off, as I mutter “thanks-!” towards her back.
If only more people had her courage.
Look, everyone’s scared. Scared and tired.
We’re frightened by the economy. By Ebola. By ISIS. By the Kardashians.
What is this world coming to? Are we really safe in it? What about next year, our next paycheck?
Are we going to be able to find a good-paying job when we graduate from school?
Is our new startup going to take off, or fall flat?
Are we ever going to find another woman we love as much as Susan?
Will we ever find true love on the Internet?

All the foregoing reasons are why it’s so crucial that you approach that stranger you find attractive and shyly say, “Hi” with a sideways glance and a smile. If you can, brush their arm “accidentally” as well.
If they reciprocate with any kind of fluttery smile, awkward stammering, or throat-stopping f*ck-me eyes, it’s your responsibility to have a candid and sincere conversation with them.
You could say:
“Look, isn’t it strange how our society is so disconnected? Everyone’s head down, looking at their mobile. Is this how it was meant to be?”
Or you might say:
“You don’t have Ebola, do you? I’m just kidding. Isn’t that a ridiculous health scare?”
Or even better:
“I never talk to strangers, but I wanted to talk to you. How’s your day going?”
A candid and sincere conversation between strangers is a rarity.
Unless we live very near the equator or in a particularly friendly small town, most of us settle for scripted and insincere conversations with people we’re very familiar with – our coworkers, fellow students, friends, and even family.
This is the line in the sand. This has to stop. No more insincerity. No more social scripts.
Let’s go off the script entirely. Tear the page. Say something outlandish and totally true. “Sorry, I was caught off guard because of your cleavage.” Be bold! Boldness has a magic and a genius to it, to rip off Geothe.
Let’s face facts: this person might not live to see another sunrise. An asteroid might crash into you both in the next minute. You might be the last two people to talk to each other. So make it real. “That’s some amazing-looking kale.” It could be the beginning of a beautiful friendship…or it could just be a passing comment exchanged between two ships passing in the night. It doesn’t matter. You have to try.
Think of yourself as the sun. The sun has a big job: it produces the energy equivalent of a trillion 1-megaton atomic bombs every single second.
But because it does that job so naturally, all the plants, animals and people on this planet survive and thrive.
You have a sun-like job also: shine kindness and warmth on everyone you meet. You don’t need to shine megaton-levels of kindness on everyone, but just a little will do.
Be the giver of good vibes. Be the radiant light energy that warms everyone up. Be so present and immediate and warm that people blossom when you come around.
This is a very isolated world, a very cold world. Technology increasingly interposes screens between us and our experiences (time for a selfie!) and us and our friends (like my new instagram!).
In this electronicized world, it’s important to keep your mobile phone in your pants’ pocket and greet people with a smile and a few warm words, instead.
Online dating isn’t helping! Stop swiping, start smiling.
Okay, you’re shy. I understand that. I’m shy also.
But don’t let that stop you from being the sun in someone else’s sky. Be the shy sun if you must, but be the sun.
If you’re shy, awkward, or an introvert, no problem. Awkward people are awesome. Introverts are some of the coolest people I know. Develop your radar for finding other shy, awkward introverts, and start talking to them. They’ll appreciate it, trust me.
Unless they run away awkwardly, in which case, at least you tried.
Since one of the biggest questions I get on this topic is “But what do I SAY to an attractive stranger??!” I’ve decided to indulge you by writing down 100 of my best ideas.
Note I didn’t see these were 100 of THE best ideas, just MY best ideas. You may have better ideas.
But if I can come up with 100 things, that means you can to. Part of being candid and sincere is using your own words, not someone else’s words. Using someone else’s conversation starter is akin to having Cyrano de Bergerac write your love letters: it might be effective for a moment, but ultimately you’re just farming leads for Cyrano.
100 THINGS TO SAY TO START A CANDID AND SINCERE CONVERSATION
1. Hola.
2. I’m [NAME], who are you?
3. I’m worried about [X thing you are worried about.] Any advice?
4. What color would you say this sweater is?
5. What’s your dog’s name?
6. Do you believe in the Loch Ness Monster?
7. Do you know any astronauts?
8. Are you good at math? I need to multiply two numbers.
9. Can you recommend a good dessert place around here?
10. Hello.
11. How’s your day going?
12. Is there a park near here?
13. Where’s the nearest Starbucks? (in front of a Starbucks)
14. Nice bangles.
15. Hi, I have to run, but I just had to ask you…
16. You have lovely eyes.
17. I know this is socially awkward and not really permitted, but I just wanted to say hello.
18. Aloha!
19. Buenos Dias.
20. I wish it would rain. (clear up)
21. I never do this, but I wanted to say hello.
22. Let’s meet each other.
23. Have you seen my dog?
24. Buenos Noches.
25. [Extend your hand without saying a word]
26. Would you care for a dance?
27. Any good restaurants around here?
28. Buenos tardes.
29. Can I pet your dog?
30. That’s a very pretty gold pendant.
31. Did you see the sky this morning?
32. Excuse me.
33. Do you live in the neighborhood?
34. Could you recommend a brand of dog food?
35. I’m [NAME], I don’t think I’ve met you yet.
36. Do you ever wonder if we’re all characters in a novel?
37. Have we met?
38. Looks like rain.
39. Is it loud in here, or is it just me? [in a loud nightclub]
40. Can you believe she’s wearing that?
41. I like your sandals.
42. Your dress is impeccable.
43. I’m not afraid to talk to strangers. Hi.
44. I’m way out of my comfort zone. Hello.
45. Did you hear about that comet we landed on?
46. I’m a very shallow person, and wanted you to know that I think you’re amazingly beautiful. Thanks for indulging me. Sorry for interrupting your day.
47. Excuse me. You look nice.
48. May I borrow your umbrella for a moment?
49. Would you like to share my umbrella?
50. Did the bus just pass?
51. Yes, you may pet my dog.
52. Is the train on time?
53. Are you from [area]?
54. Cindy! Oh, you’re not Cindy. I’m so sorry.
55. [Sigh] Monday again.
56. Still waking up?
57. Is this your weight? [at the gym]
58. Excuse me, you dropped something.
59. Is this your furry hat?
60. Have you seen my feather boa?
61. Do you find it odd that people don’t talk much anymore?
62. I appreciate that you’re not on your mobile phone right now.
63. Swipe right! [to someone on their mobile]
64. Did you enjoy the film?
65. Let’s be brave.
66. Ladies [or gentlemen] first.
67. Age before beauty. [or the reverse]
68. Good evening.
69. Where did you get your hair cut?
70. Where did you get that lovely purse?
71. I have to be honest, I can’t stop looking at your dress.
72. Do you enjoy the films of Christopher Nolan?
73. Do you have change for a fiver?
74. Did you vote? [on voting day]
75. Happy [holiday] [on national holiday]
76. Another day, huh? [on the transit]
77. Do you have the time?
78. How do you do.
79. There’s too much sand at this beach.
80. Do you have any sunscreen?
81. Here, take this [offer handkerchief]
82. My friends bet me I wouldn’t talk to you. So, I’m here to win the bet. How are you?
83. Are you a courageous person? You look courageous. Me, I’m very shy.
84. When was the last time you had meatballs?
85. I’m looking for a haberdashery. Do you know where the nearest one is?
86. [outside a nightclub or restaurant] May I call you a cab?
87. Did you see the review for this? [movie or restaurant]
88. Shame about the [recent tragedy], wasn’t it?
89. Lot of weather we’ve been having lately, isn’t it? [h/t to Laurel & Hardy]
90. Any weekend plans?
91. That book looks good.
92. Any recommendations? [in an ice cream store]
93. What’s the verdict?
94. It may be time for a vacation.
95. Let’s be friends.
96. Hey, don’t you follow me on instagram?
97. Do you know Paul?
98. You a Sinatra fan?
99. Are you working here?
100. Somewhere in America, Miley Cyrus is still twerkin’.
In summary: we’re always one conversation away from our next ideal job, our next amazing business deal, and our next great love affair. Or we’re one conversation away from helping someone else reach theirs.
Have that conversation today.
You’re invited to attend our FREE webinar on Dating Confidence for Men. Click here to get access to the webinar.
Featured image is a photo manipulation by Jean Yves Lemoigne.
Also published on Medium.
