How many times has email caused a headache for you?  Sometimes, it’s dealing with all the email that flows into your inbox.  Other times, it’s watching the unintended explosion caused by a poorly worded email (or poor decision to express difficult emotions).  Just yesterday, I found a new way it can cause headaches.

That’s when I found out that Ryan Hupfer hated me for the same reason I hated him.  I never returned his emails.  The funny thing is I never received them.  Nor did he receive mine.  

Before I go too far, let me give you the backstory first.  Ryan (or @Hup on Twitter) is a former MediaSauce evangelist.  A few months back, he and his girlfriend, Stephanie, moved to Palo Alto to live the dream and he is now evangelizing for Photocrank.  In a short period of time, he’s become a super-connector within the Bay area.  

A couple weeks ago, he came back to Indianapolis and had lunch with Bryan Gray and Mitch Maxson.  When Bryan heard I was traveling to the Bay area, he encouraged me to get together with Ryan.  

I got his contact information from Mitch and sent an email offering to meet for lunch or dinner.  No word back.  A couple days later, I emailed him again.  Still no answer.  By that time, I figure he’s not really interested.  

Almost out of nowhere, he posts a reply on one of my previous blog entries.  The kid has some nerve not to return my emails and then post a reply just to generate press for his new company.  So I email him back - still no answer.  Since he’s a MediaSauce alum and good friends with my friends, I visited his blog and posted a reply.

Still no answer.

When I touched down in San Jose, I got an email saying he’s following me on Twitter and saw he’s tweeted a message asking me to contact him when I hit the ground.  After a few tweets, we set up a time and place for dinner.  

At this point, I figure he’s so connected to the Silicon Valley inner circle that he’s moved beyond email.  He’s so cutting edge that he’s just using social media like blogs, social communities, and Twitter to communicate.  He’s the One (like Neo in the Matrix) and knows the secret to bending the spoon is to know there is no spoon.  

When Ryan and Stephanie arrived at the restaurant, he tells me the story of how he hated me at first because I was too good to return the emails he sent prior to my trip.  Then, he hated me more because the only time I would respond to him was by posting a reply on his blog in response to his post on my blog.

Fortunately, he gave me the benefit of the doubt, because I am a MediaSaucer and am friends with his friends.  Oh yeah, he also decided to try Twitter because Mitch Maxson assured him that I would be more likely to OVERCOMMUNICATE with him than not communicate at all.  (What are you saying, Mitch?) 

Wait a minute!  He’s telling me what I wanted to tell him. It turns out our email accounts were blocking each other’s messages as spam. 

It all worked out in the end.  We had an amazingly delicious dinner at Zao’s noodle bar on University Avenue in Palo Alto.  Ryan stole my joke about noodle bars.  Stephanie endured dinner with two overcommunicators.  Scott got to eat at Red Mango (original yogurt with fresh mango, raspberries, and Ghiradelli’s Dark Chocolate chips. 

When I got back to my hotel, I sent Ryan an email to both his email accounts.  Still no reply.  Because we have been trading tweets on Twitter off and on all day, I know he doesn’t hate me. 

Fortunately for us, we didn’t let the fact that our email accounts have issues keep us from making a connection.  By using blogs, twitter, and other social media, we figured out the other guy was worth meeting for dinner.

So what’s your funniest email story?  

This entry was posted on Friday, June 13th, 2008 at 2:27 am and is filed under blogging, social networks, web 2.0. You can follow any responses to this entry through the RSS 2.0 feed. You can leave a response, or trackback from your own site.