Retargeting Isn’t Annoying - If You Do It Right

You looked at a pair of boots once - now they’re following you across the internet like a lost puppy.
You didn’t click “buy.” You didn’t even add them to your cart. But now, whether you’re checking the news, watching a cooking video, or reading an article on why retargeting feels creepy, there they are again: boots, showing up two weeks after you already bought different ones.

That’s what bad retargeting looks like.

When retargeting goes wrong

Retargeting has a purpose: to re-engage someone who showed interest but didn’t convert. The problem is, many brands treat it like a second chance to copy-paste the same message - louder and more often.

Here’s where it usually goes off the rails:

• No progression.
  One ad rarely seals the deal - and that’s okay. But if every follow-up just repeats the same headline, same image, and same pitch, people stop noticing. That’s banner blindness: their brain registers it as “already seen” and tunes it out.
  And when nothing changes - no new angle, no shift in tone, no sign that you’re paying attention - people don’t feel guided. They feel ignored. It’s not just a missed opportunity. It’s a conversation that never moved past hello.
• Poor placement.
  Context matters more than many marketers admit. If someone’s reading an article on productivity hacks or watching a video on how to fix a leaky faucet, they’re probably not in the mood to shop for luxury watches or all-inclusive vacations. Even if your targeting is technically correct, bad placement makes the message feel irrelevant - or, even worse, remembered for the wrong reasons.
• No behavioral awareness.
  If someone buys your product through Amazon, a third-party retailer, or even in-store, you often won’t know. That’s one of the biggest blind spots in retargeting - and it’s how people end up seeing ads for things they already own. Without a clear signal, many campaigns default to showing the same generic message to everyone, regardless of where they are in the journey.

What good retargeting does instead

Retargeting isn’t just about reminders - it’s about making progress.
You’ve already captured a bit of attention. Now it’s about guiding that person down the funnel - from interest to consideration, and eventually, to action. That means each ad should do more than repeat the message. It should move the conversation forward, offering something new, relevant, and timely based on where they are in the journey.

So what does that kind of progress look like in practice? It usually comes down to a few key behaviors:

• It evolves the message.
  Effective retargeting doesn’t repeat the same pitch - it moves the story forward. Each follow-up gives the customer something new: a benefit, a proof point, a timely nudge.
  Think of a skincare brand: the first ad says “See our new line.” The second follows with “See the difference: before-and-after results from real customers.” The third closes with “9 out of 10 customers saw results in just two weeks.”
  Each message builds on the last. You’re not just staying visible - you’re building a case.
• It respects context.
  Smart retargeting doesn’t just care who you’re targeting - it cares where and when. An ad that feels relevant on a shopping site can come across as tone-deaf on a blog about burnout recovery or during a midday scroll through recipe videos.
  Context shapes how your message is received. If the ad feels aligned with the moment, it has a chance to connect. If it feels like an interruption, it’s forgotten - or worse, remembered for the wrong reasons.
• It reflects behavior.
  One of the biggest challenges in retargeting is what you don’t see. If someone buys on Amazon, through a retailer, or offline, you often won’t know - but that doesn’t mean you should assume they didn’t.
  Instead of repeating the same offer, try to use that retargeting slot for something relevant to both buyers and browsers: tips, accessories, how-to content, or social proof. If they’ve purchased, it feels like a helpful follow-up. If they haven’t, it still builds trust - without overselling.

A second chance isn’t for copying - it’s for closing

Retargeting has a reputation for being repetitive - and often, it earns it. When the message doesn’t change, it starts to feel more like background noise than a helpful nudge.

But that’s not the medium’s fault - it’s the marketer’s.

Effective retargeting doesn’t repeat - it responds. It builds on what the customer has already seen or done, offering sharper benefits, clearer answers, or the next logical step. The goal isn’t visibility for its own sake - it’s forward motion.

Here are a few things worth keeping in mind:

• Retargeting is your follow-up - don’t waste it
• Respect the customer’s attention
• Make every ad feel like a value-add, not a broken record
• And maybe leave the boots alone - they got the message