Blog Post #3: When AI Knows You Too Well: A Personal Encounter with Outlook Clothing’s Marketing

 Not too long ago, I found myself scrolling through my inbox when an email from Outlook Clothing caught my eye. It wasn’t just another generic sale announcement—it referenced a jacket I’d purchased months ago and offered a few new arrivals that perfectly complemented it. At first, I was impressed. It felt like the brand had actually seen me—not just in the transactional sense, but in a way that acknowledged my unique style.

But as I read further, I realized something: the email was efficient, but it wasn’t quite human. It was polished, yes, but there was something robotic about the way it presented the suggestions. Despite the relevance, I didn’t feel that spark of excitement to click through. Sure, I appreciated the thought behind it, but the email lacked personality. It felt like Outlook was trying to build a relationship with me, but the conversation was missing the warmth. A more playful, engaging tone might’ve grabbed my attention more. Maybe a cheeky "Hey, we thought you’d look great in this!" or an exclusive, limited-time discount would have nudged me toward action.

Later, as I scrolled through Instagram, I noticed a targeted ad from Outlook for their new fall line. This one, though, felt different. The ad was not only relevant but timely—it appeared right after I’d posted a photo of myself in my Outlook jacket. This time, it wasn’t just an ad; it felt like a recommendation from a friend who knew my taste.

AI marketing can be brilliant when it’s on-point, but it still needs that human touch to make it feel less like a push and more like a connection.