I don't think that's it. I've never been one to shy away from any difficult emotional experiences I have (maybe I'm wrong though who knows)

I just end up feeling emotionally "flat" after doing it. Which sometimes feels like that's the goal, but I don't like the feeling

Ah, I see, that's also very common. Taken all the way it can develop into nihilism, which is one of the two extreme views in Buddhism [1]. I fell into that early on and abandoned my practice for many years. I found that once I found the Mahayana teachings on emptiness [2] and then the stories of the Vajrayana masters [3] the practice became joyful again and not bogged down by some narrow view of what meditation is.

[1] https://www.rigpawiki.org/index.php?title=Two_extremes

[2] https://en.wikipedia.org/wiki/%C5%9A%C5%ABnyat%C4%81 and particularly as formulated in https://en.wikipedia.org/wiki/Prajnaparamita

[3] for example Saraha: https://en.wikipedia.org/wiki/Saraha and Tilopa: https://en.wikipedia.org/wiki/Tilopa

Did you noticed the Sri Yantra pattern in the Prajnaparamita article?

https://en.wikipedia.org/w/index.php?title=Yantra