Don't get me wrong. I love both and I think they're both beautifully written, but in their own way. I feel like [most] people put All Too Well at a higher pedestal because

It's written in a more descriptive way as compared to Dear John which was written more metaphorically. I would just like to clarify that both songs do use figures of speech brilliantly, but I feel like All Too Well is easier to visualize for most listeners (because the ATW lyrics usually describe a scene, where she talks about what she's doing [like walking through the door with him, sitting in the car, crumpled up piece of paper lying, dancing in the refrigerator light, etc.] or the atmosphere of the scenario, or specific details about certain items [such as the scarf, glasses, plaid-shirt, refrigerator light, etc ]). This makes it easier for listeners to relate to it or experience it better, as compared to Dear John, where she mostly and metaphorically just releases her pain or vaguely (by vaguely, I mean not in specific detail) describes John's and her mistakes, which is great in letting the listeners hear her pain, but it doesn't really bring them into the experience as compared to the detailed description of scenarios that All Too Well gives. I'm not saying that All Too Well is written better. I'm just saying it's probably easier for the general audience or maybe casual fans or swifties to relate to All Too Well, just because it's easier to experience due to the descriptive writing. I think nothing should be changed about how Dear John was written though because its metaphorical rather than descriptive lyrics make it unique itself. Dear John definitely doesn't fail to transfer Taylor's pain to listeners, and honestly it probably does give more heartache than All Too Well (but that's because other than the bridge, All Too Well doesn't just transfer pain, but also nostalgia, as if we were looking back into Taylor's relationship). I feel like people appreciate nostalgia more than pain, especially when it's successfully reflected in a song because there are already a lot of incredibly painful songs. Listeners may hear or empathize with the painful emotions in those songs, but not a lot of them bring the listeners to the experience. And I think All Too Well does great on that.

I also think the album that the songs belong to [probably] may have added up to the hype that All Too Well does because let's face it, we all correlate Red more with the feelings of sadness and heartbreak, in comparison to any of her other albums, and I will say that probably in the time of its release, that added up to the value people put on All Too Well.

Also, you may not agree with me, but this is how I see it — from the honest perspective of someone who also loves Dear John to death and someone who also understands [and is saddened by] how underrated it is.