So, first off, let me just say I am not a big runner. I run sometimes, mostly on treadmills, frequently if I have a ball someone else wants, or someone has a ball I want – you know, stuff like that. Running “sometimes” means I only have to replace my running shoes every so often, and “every so often” has arrived over the past month. It’s officially time for new kicks.

Of course, before I saunter up to the “Great Wall O’ Sneakers” that adorns every sneaker store and peruse my selection, I like to do some online shopping. If I get a little research under my belt, I can be smarter about the usual selection of new fangled running shoes featuring the latest in material (“It’s a new rubber-titanium-vinyl-hemp hybrid!”) and advanced cushioning (“This shoe supports your arches, heels, tonsils and eyelids!”) and be better prepared to try on a pair or two.

Well, for the first time, I decided to start at Zappos – Zappos is often pointed to as a model for what a digital and social retailer should be, so I felt like it was time to let the Zappos experience wash over me. I went to the site and was 3 pairs of Nike sneakers into my exploration, when I had to abandon the mission to attend to one of the many other aspects of my life more important than new running shoes. I put the sneaker purchase process on ice for a day or two.

Soon after, I was minding my own business – catching up on terrible ideas for rebuilding a Boston Celtics team that is aging in dog years – when I saw out of the corner of my eye, hiding just above the forum topics, the sneakers I had viewed on Zappos, but decided not to buy. Ah, I see – Zappos wanted to follow up with a quick “you look busy, but you had these sneakers of ours on your screen for at least 45 seconds – want to buy them now?”

“Well, no,” I responded to Zappos in my head, “I don’t, really. I was just doing research, and anyway, all you’re doing is showing me the sneakers I already looked at. I didn’t forget I just wasn’t interested enough to buy them… and it was just a day ago.”

Over the next day, the sneakers showed up again and again, no clever message, nothing more than the same sneakers, staring at me like a sad little puppy waiting to be adopted, “Can you take me home now? How about now? Or now?” They followed me to Boston.com:

And then later on, as I checked in on Boing Boing – hey!  It’s those sneakers again!  I made eye contact for a second, and now they won’t leave me alone…

For 3 straight days, they showed up everywhere – when I read reviews on Pitchfork, caught up on spring training news on Sons of Sam Horn, explored clever tidbits on Laughing Squid. I was genuinely surprised when they didn’t show up in my medicine cabinet in the morning before work.

My point? Having been in digital media for a long time (read: since I had a full head of hair – a full head, I tell you!) I am not one who is easily perturbed when I am behaviorally targeted by an ad. If someone is going to serve me an ad, I want it to be relevant. That only feels right. In fact, I often revel in well played retargeting – special offers, “people who looked at X also looked at Y” messages, anything. What I don’t like is being hit up with the same product, over and over again, like eventually I’ll change my mind about these sneakers after all this time, or I’ll become so worn down by this series of “how about now?” moments that I throw my hands in the air and decide to buy them just so they leave me alone.

More importantly, this feels like a missed opportunity. We are in a space where brands and companies are finding success by putting some level of humanity at the core of their digital presence, and this approach feels like the opposite. For example, if I had this experience with a real human, say, a bartender, I’d never drink at that establishment again – “How about an IPA? Mmm, the IPA is good. Why don’t you try the IPA? Have you seen our IPA?”

So c’mon – get creative with it. How about an offer? What about free running socks? Or even something clever and unexpected – show me your green running shoes while I am on CelticsBlog. Ask me a question so you can follow me with more relevant sneakers in a way that helps you narrow down the choices for me, while still helping me explore new options. Look, if you are going to go through the trouble of identifying me as an individual, and trying to target me with marketing as an individual, talk to me like a human. Don’t waste all your retargeting efforts on nothing but a repetitive series of “how about now?” moments.