The simpler explanation, with a grounding in marketing and cognitive science: we basically train ourselves to ignore ads. If successful our active brain doesn't register, while our passive brain might. Have we recently activated subject X in conversation, we notice ads around X a bit more. Hence the creepy feeling.
Another explanation might be: I just discussed a holiday and promptly got an ad for the exact island. The person visiting me probably uses Facebook, so FB knows we were together and knows where he went via location. Logical conclusion: people discuss intercontinental trips and hence: show ads.
I feel the same way about this "my phone is recording me" thing as I do about Bigfoot. I really want it to be true, but there's so many people walking around with phones all the time everywhere that it seems like it would have been caught by now, so I'm starting to think it's just not true.
That has been an issue for several years. Several companies have been secretly recording your screen and (deliberately or not) recording your PII. I always read privacy policies but it seems like it is not enough, either. I believe Google should be very cautious when it comes to such analytics vendors (e.g Appsee et al).
On vacation this week. My wife accidentally bought some Flaming Hot Sweet Chili Cheetos instead of the regular kind. They were talked about many times the first evening. Yesterday my wife is scrolling through Instagram and what does she see? Flaming Hot Cheetos. How?
Her credit card and per item purchase history is in a database somewhere linked with her social network identities. Combine that with targeted ads and you have a consistent personal reminder of your purchase history.
I'm not saying that's wrong, but why would Cheetos advertise to someone that just bought Cheetos? I don't know much about how advertisers by these types of ads, but why would someone throw ads for something that was just bought? Wouldn't they wait until next month or something?
Maybe because she just bought that variety of Cheetos for the first time. They're trying to promote repeat purchases.
Of course, when there are millions of opportunities for coincidences to occur, and when coincidences are much more memorable than non-coincidences, the chances that everyone has a couple of these stories is pretty high.
I've heard this, and it's a reasonable explanation.
It'd be interesting for someone to make a browser extension which logs all the ads you see, allowing trends over time to be spotted. It would also allow hard evidence in a situation like this.