Picking up a girl is easier than talking to Chris Brogan

(Chris as promised, I have some tips for you at the end of this post. Hope that they’re valuable to you!)
THE Chris Brogan had just finished speaking at a panel with Ben Huh and Micah Baldwin that was moderated by Sean Percival. I tried to catch him after the panel, but was unfortunately beat to the punch by at least 5 other people who got to Chris first. It was like when you see a hot girl at a lounge or bar, she’s never standing by herself because she’s always surrounded by guys trying to get her digits. That’s how this felt right now, except these people wanted the business card in Chris’ pocket.
In the Game, you never want to stand with the group of guys waiting for your chance to talk to the girl. This demonstrates lower value and makes the person unconsciously think less of you from the very beginning. I decided to step back and talk to some other people while keeping my peripheral on Chris.
Being the “hot girl” at the conference, Chris was constantly engaged in a conversation for the next hour or so. I decided to suck it up and try to engage Chris and all of the people that he was speaking with:
Lets see, what should my opening be… “Hey guys, I had a question about blogging that I hope you can help me with…”
No, that sounds lame. How about, “Hey did you guys hear about the guy who traded a red paper clip for a house…” Jeez, how old is that news. Be more relevant…
I decided to forget the opening line and just politely ask to be able to listen in on the conversation because I’m eager to learn from them - you know, Tim Ferriss style. To my dismay, not only was Chris talking to another gentlemen, but he was also actively engaged with AV Flox. So now I’m all flustered because Chris Brogan is HOT in the social media world and AV Flox is HOT as a human being. I had been building all of this up in my head so much that I just gave up and sunk my head down back at my seat…
I’m a very confident, outgoing person, but I admit that it is very intimidating trying to talk to people that I admire or look up to. In a way, picking up a girl is easier because if she doesn’t like you, then you really have nothing to lose. Actually, you feel good about yourself because you had the balls to talk to a hot girl and you probably made her day because being “hit” on is flattering - of course if you’re a creeper, then you probably just ruined her day.
With Chris Brogan it was intimidating because if I made a fool out of myself, then I did have very big things to lose: my personal brand, my company brand that I represent, and a valuable connection in the social media business world. Even though Chris is probably the nicest, most openly friendly person that I can think of in the blogosphere, I was still intimidated because of the following reasons:
- I was afraid I might sound dumb
- He was constantly surrounded by multiple people so it was hard to talk to him by himself
- It’s human nature to be afraid to talk to someone new
I actually did have the chance to have an amazing conversation with Chris (which is evidenced by the picture above). For those of you who get as nervous as I do when speaking to people you admire, this is how I did it:
1. I caught him right after he was done speaking with someone else
Ok, this might be partly luck on my part. This is what happened:
Jason Calacanis began to tape a LIVE showing of “This Week in Startups” right in front of my table, so Chris decided to stand near my table for a clear view. A few of his fans came up to him to take some pictures with him, so I decided that this was my chance to pounce. I walked up next to them pretending to get a clear view of Jason Calacanis (again, using The Game tactics and not waiting in line to speak with him), and immediately said “Hi” to Chris once his fans took a picture with him.
Key Takeaway: If you’re scared of approaching someone when they’re in a group of people, then you’re just going to have to patiently wait until they have some breathing room. Remember to not look like a stalker by just blankly staring at the person while waiting for him. If you have to, pretend to be doing something else (like talking on your phone) while you wait for your chance to pounce.
2. “Just suck it up and do it”
In order to grow the balls to talk to Chris, I thought about what were the worst things that could happen. What is the worst possible scenario if everything goes wrong? And you know what, I really came up with nothing. Sure, I could sound dumb and Chris might think that my business idea has no chance of succeeding, but as long as I’m respectful, honest, and humble, I saw no negative repercussions from speaking to him.
I then thought about the positives (making a new friend, establishing an awesome business connection, having a cool story to write about on my blog) and they greatly outweighed anything negative. The biggest thing holding me back was my fear of the unknown.
To dispel that fear, I took a deep breath, and told myself, “Just suck it up and do it.” Sometimes you just need to give yourself a good kick in the butt.
Key Takeaway: Rationally step back and take a look at the positive and negative outcomes that can result from the decision you’re about to make. Once you have logically thought through it, just say to yourself, “Suck it up and do it!” It works wonders for me.
3. Humble confidence, honesty, and respect
I used no opening lines or gambits. I walked straight up to Chris, extended my hand and introduced myself:
“Hi Chris, my name is Jun Loayza and I’m an avid reader of your blog and greatly admire everything that you have accomplished. I know that you’re busy watching Jason speak, but I was hoping that I could have a few minutes of your time to get to know each other better.”
That’s all I had to say and Chris was more than happy to sit down with me and chat about business, social media, and life.
Key Takeaway: If you stick to portraying humble confidence, honesty, and respect, then you can’t go wrong. Not everyone will make the time to speak with you like Chris did for me, but at least you will get the positive attention of the person and perhaps a chance to speak to him the next time you run into each other.
—
During our conversation, I admitted to Chris that I was nervous before speaking to him. Being the great guy that he is, he asked me what he could do to change that and have everyone be comfortable enough to just go up to him and chat with him.
I couldn’t think of anything at the time, but thought of something just now.
Chris, this is something that you could try:
I read this story about how a couple of dudes met Shaq at a diner by using Twitter. Now, they were too shy to walk over and say hi to Shaq, so Shaq actually encourage them to talk to him with a Tweet. He then ended the meet up with this Tweet:
“To all twitterers , if u c me n public come say hi, we r not the same we r from twitteronia, we connect”
I know you’re constantly bombarded with people at conferences, which means that the shy ones are to scared to actually come and chat with you - especially if you’re in a group of people. You could try and take a page out of Shaq’s book by doing the following:
- At conferences, you could Tweet something like, “Hey, I’m really looking forward to meeting some young bloggers here. If that’s you, don’t be shy and come and say hi!”
- If you’re talking to a group of people, you could Tweet something like, “Having a great conversation with @Yukai_chou and @Joseph_Yi about startups. Come sit down with us and join the convo!”
- If you find yourself relaxing alone and could use some company, you could Tweet something like, “Sitting by the cafe and reading over some email. Come by and say hi if you’re nearby.”
Hope these are some helpful tips!
Thanks Chris, it was truly amazing meeting you.




Very funny post. There is such a hunger for getting to connect with people, but in the end, one of the cons of a strong social media presence (and Chris is one of the best) is the ability to mange the requests and still stay productive. Some nice tips here. Hope you are well.
Yup, doing very well. Had a lot of fun at Twiistup and really happy to have met such great people.
Yea, I’m sure when you’re Chris Brogan status, people are constantly trying to meet you
I love this! That is awesome that you got to meet someone so influential in social media and also an overall person
I love his line: what he could do to change that and have everyone be comfortable enough to just go up to him and chat with him
I hope one day I can talk with him
Glad you liked it.
Can’t wait to meet up tomorrow for some good work!!!
Great take-aways Jun! I think this is useful for meeting anyone you admire from any background. It’s very cool of Chris to be so open to meeting new folks and so friendly; I’m sure he’s just swamped. I’m a big fan of his as well, so congrats on getting a chance to chat with him.
Thanks Cody.
I wonder what it feels like to be that status? Hopefully one day I’ll know the feeling, and be able to give back to young entrepreneurs who approach me
I was with a friend between panels at sxsw, and he started freaking out about seeing someone “famous.” He spotted someone he idolized (Chris Brogan), but was too nervous to introduce himself. I’d never heard of him back then, but even if I had, I’d have still given my friend the same advice I gave him then.
If you want to talk to someone, do it.
There are three possible outcomes-
1. They’ll be a dick.
2. They’ll be polite then excuse themselves.
3. They’ll be cool.
Chances are, #2 or #3 will be the case and you’ll have a great story.
Seriously though, they’re no cooler than you or I, they just have had the luck or drive to harness their skills or talents to become well known and successful. I’ve had the good fortune of working with all kinds of amazingly well known, talented folks and they are just as normal as us.
Way to keep it simple!
The hardest part is just getting over the initial fear of meeting someone new. It’s all psychological, and if you can harness your inner-confidence, then you have a huge edge amongst your peers.
Ha, this is a great post! I frequently feel like all of us swimming around in the world of blogging and social media could take a cue from the “rules of dating.” It’s great to see some of those rules put into action and to know that Chris really IS as approachable and nice as he seems online.
I also get where he is coming from on his end of feeling a little weird and bad. This is a rather silly story, but in one of the organization I was a leader of in college apparently people were very much intrigued by me. One of them “finally” approached and met me “in person” at a pub local to campus. She described it to someone else in the group (who was a good friend of mine) and said “I met Elisa…it’s like I’ve met the Buddha!” Talk about a reputation to live up to…as far as I know I do not have an entire religion of followers!
We build people up to be a characture of themselves in our mind, when in reality they are sometimes just as awkward and nervous and shy about meeting us!
It’s amazing how much the “rules” of dating really do apply to business situations.
Hahaha, I’ve never thought of it that way. Being called the “Buddha” of something would be very shocking to me. It would be extremely hard to live up to it and I guess I would feel a bit pressured.
Then again, I feel that if you’ve earned “Buddha” status, you should be able to humbly accept the fact that people look at you for inspiration and knowledge.
I agree. It’s all psychological
First, people should be in line waiting to talk to YOU. Me? I’m just a typist. You’re DOING good things, man. So, thank you for your time.
Second, to everyone not named Jun, I am *so* a normal guy. The fact I have a following is because I’m an overnight success with over 10 years of hard work and ramen noodles under my belt. I’ve got every failure story that you have, and now, I’ve got some success stories, too.
Third, if ever I’m mobbed, Jun’s ideas above were AWESOME at fixing the problem and he slipped in as casual and slick as if he had been professionally connecting for decades (which is almost true).
Awesome post, Jun, and I can’t wait until I get the opportunity to work in one of your huge companies in the future.
Glad you liked the ideas Chris.
Hahaha… that would be the day. I’ll keep working hard and I hope to one day catch up to you.
This is an awesome post, man! I’m glad you got a chance to meet and talk with Chris. He’s an awesome guy and has a wealth of knowledge to share. AND he’s funny and REAL! But you’re totally right. Be courageous, be direct and be ready to listen, learn and share.
Hahaha… I like your name “wingman”
So, what are best practices as a wingman? I’m “winging” for a friend this weekend because I have a girlfriend and he doesn’t
This is awesome, Jun! I love your analogy to using The Game in order to approach anyone…. I am familiar with Chris, but not that well acquainted with him, beyond knowing that he’s one of the big hitters in the industry. Your description of how down to earth and open his is makes me an instant fan. I love that quote from Shaq too… “we are all from Twitteronia”… Brilliant! That’s why I love twitter. It makes almost everyone instantly approachable.

Karen
(@Dreaminthelife )
Shaq seems like a cool guy. I hope to meet him in a diner some day.
I’m glad that I’ve made you an instant fan of Chris. He is truly a one-of-a-kind guy.
Hope to meet you some time at a social media event
Jun, if you didn’t have a girl, I would be questioning you right now.
Great article. Awesome references to Neil Strauss’ “The Game.”
I find a good way to approach someone is have something relevant to ask about, some sort of common ground. Get the person talking about themselves (people love that). Then share something about yourself so self-disclosure is balanced on both sides.
Hahaha…
Finding common ground is always great. The hard part is usually finding that common ground.
I think it’s that initial ice breaker that gets more people. To me, it’s as easy as just walking up to people and saying “hi!”
However, when it’s someone who I admire, I think too much in my head about what I should say
Jun, the only thing that matters when you are a wingman is this:
“If he’s a true friend, then as far as you & everyone else is concerned, he is the best person on this planet. Never leave him behind & help him have a good time, no matter what it takes.”
Joseph has some good points there. Listening, relating and sharing.
Well well - Jun Loayza and Chris Brogan is one blog post - complementing one another with all humbleness is great see.
As usual Jun - great post indeed and awesome tips
Thanks Khalil.
Maybe one day Chris Brogan will write about me!
Great post, I’m glad you shared that experience it was very helpful. I can’t count how many times I’ve pretended I was doing something while waiting to approach someone who was a magnet to a crowd. I thought I was the only one who did that haha. I’m not very familiar with Chris Brogan, I’m going to have to check him out.
Hahahaha… guess we’ve both read the game then huh
Chris is an awesome guy. Definitely check him out and reach out to him through twitter and his blog. He’s usually very responsive.
If he doesn’t respond, it’s just because he’s bombarded with too many emails. Keep trying though and I’m sure you’ll get through
Some of us have been around so long that we remember networking before there was on-line communication. Just like public speaking, it is something that gets much easier the more you do it. You find that very few people mind being approached. Even in Japan, which is very formal, if you are at a public program it is understood that people will be talking to each and of course exchanging cards.
I worked in Japan for 20 years, hosted the Chamber of Commerce in Japan Marketing Program meetings, participated in the business networking arm of the Economist and founded Women on Top. This was pre-LinkedIn so I needed to keep a database in FileMakerPro (which I still love) and made sure to send out a snail mail greeting at least once a year (seasonal greetings are very Japanese).
Social Media and particularly Twitter makes it much easier to keep up with people and participate on a fairly level playing field with meaningful @’s. As has been said here, we are all just people. Just like “picking up girls,” some meetings might actually become relationships and most will remain acquaintances but don’t let life pass you by without reaching out.
Gosh, I want to go to Japan and experience the life over there! The social dynamics and interaction must be so different, huh?
People write a lot of posts about how Twitter has deteriorated our form of interaction and that we now blur the lines between friends and acquaintances. I disagree completely, but every has their opinions
Jun, I love this post! It’s so honest and I know how you feel.
Sometimes it’s all a mind game to psych ourselves out, but then once we do it (talk to someone we look up to, a hot girl or guy, etc.) it usually isn’t as bad as we think. Seriously, what is the worst that would happen?
PS. I work with Micah, did you enjoy his funny stories?
Amazing post!!
I really appreciate how open and honest you are about your nervousness in meeting Chris. I too am a confident, outgoing person yet I also found myself nervous for the same reasons you outlined. Reading this post, I felt like I was reading my own thoughts and feelings. So thanks for that! I also love how you compared meeting him to picking up a girl. Very clever.
I think your tips for approaching him are very helpful and the advice you offer Chris would definitely make the approach easier.
Thanks again!
Amber
Great Blogpost. I often go to big event and see someone big there. So I have the same frustration you had here. And I like the way you put it: Humble Confidence, Honesty and Respect. I consider that’s a great attitude.
Chris sounds a great guy. I hope one day I can talk to him too!
Thanks for the tip Jun. You can’t go wrong w/having humble confidence, honesty, and respect when approaching people. 9/10 They will be nice to you as well.
And if they blow you off, they’ll at least do it nicely.
I also like the “Suck it up and do it” part. Sometimes, when I am about grapple (brazilian jiu jitsu) w/someone heavier and stronger than I am, I feel intimidated.
But I just suck it up and do it. The experience just makes me stronger.
Great post!
The easiest way to meet Chris Brogan, show up to PodCamp, sit down, have Chris sit down next to you.
We only talked for a couple of minutes (someone came and tore him away from the table), but he’s down to earth and funny.
Big lesson here, don’t be intimidated, everyone is just a normal person and if you approach them as a person and not a celebrity they’ll appreciate it.