People really like serendipity. It’s why romantic comedies do so well and people love hearing stories about random encounters at airports/grocery stores/any everyday place. It’s also why Stumbleupon and the explore feature on Foursquare are so popular. Because of the social web, serendipity no longer means running into the love of your life at a coffee shop (although, I suppose it might). Nowadays, it also means discovering new interests, stumbling upon new places, meeting new people, and having new experiences.
Yet when there’s an online/real-world interface, emotions get tricky. While the missed connections section of Craigslist may be teeming with posts searching for second chances at serendipity, the initial excitement about the use of apps like Highlight has dissolved into annoyance at best and being creeped out at worst.
Searching for Relevance
There’s a right way to engineer serendipity (even if no one is sure of what it is yet), and while it might seem counter-intuitive, serendipity is often engineered. We are all creatures of habit. We tend to stay within certain neighborhoods, go to the same places, shop at the same stores, and buy the same things. We make conscious decisions to change our habits and explore new things. There’s a fine line between serendipity and randomness. As Jeff Jarvis pointed out, randomness is easy; it’s seemingly random, but ultimately relevant that is difficult, especially on the internet. Finding this unexpected relevance gets even more difficult because there’s a selection bias. It happens in the information that we share and receive from others because we tend to be friends with people who share similar interests. Many sites rely on algorithms based on your activity to recommend pages and friends that creates an often unseen internet echo chamber. So we often either get the same humdrum, or an injection of random. It can be annoying to have to filter through irrelevant to get to the gems, but it’s worthwhile.
Creeping Me Out
Serendipity is only creepy if you let it be. Recently, the potential for creepiness with social media and serendipity has raised a lot of eyebrows and plenty of alarm, especially with apps like Girls Around Me. The problem isn’t really the way that we think about privacy settings, but how we think about who we are online and what we’re sharing. There might be something to the days of AIM, when we were in elementary school and told never to release any personal information on the internet, even our own names. People act differently online now that they know they’re being branded and that their data is being used and watched for various purposes, nefarious or otherwise. Apps like Path were supposed to be our entree into social networking without worrying about who we were sharing with, but it turns out that they were a little creepy themselves. So the best advice is to be mindful and yourself.
Finding New People
Remember the days of MySpace? Before it was all about bands and was actually MySpace and not My____, you probably spent hours rearranging your Top 8 and making changes to the HTML so that your profile looked just so. You also probably met a lot of 
people whom you never would have met otherwise because you clicked accept when strangers (who didn’t seem creepy) added you as a friend. Would you do the same on Facebook? Probably not.
The structure of social networks have changed since MySpace, for better or worse. There really is no place to meet new people anymore. There’s too much personal information that users get access to if they connect on Facebook or Linkedin. Twitter, Tumblr, and Pinterest are a few of the only networks where it has been deemed socially acceptable to follow/friend strangers, but these networks have their limitations. They don’t really have profiles or ways to continuously message people, and while this may be part of the reason why people use them as a way to connect with strangers, it also hampers further development of relationships and makes users move the actual social networking to other sites. Sites and apps that want to create serendipity could take a hint from sites like these in fostering communities where it is deemed socially acceptable (and not scary or creepy) to meet people.
Maybe we’ve become cynical or finally started listening to the advice from our parents about not talking to strangers, but ultimately we’re the ones who are killing serendipity by deeming it creepy. We don’t have to add every stranger to meet new people, nor do we have to publish the minutiae of our lives to discover new relevance or friends. We just have to be patient, smart, and a little optimistic to keep serendipity alive.
What do you think about the possibility of serendipity? Have you had any serendipitous moments online? Let us know in the comments.
