strawb. said
I'm starting to think I become obsessed with the object/subject of the obsession because I believe they hold a promise of happiness for me.
I think there is a possibility of this. I mean, it's human nature to seek out happiness right?
Im very plutonian myself. Having been both the obsessed and the obsessee (lol) I am very sensitive to this. I have been morbidly obsessed with people it starts out as like a high but then degenerates into emotional cesspool, its truly painful and AWFUL. I wish I could find it "fun" too but it has consumed my life in the past. Alternately I have been the object of others' obsession and it feels really, very yucky and disgusting. I can say when I as the other person sensed the obsession and its an extreme turn off. I find when obsession is mutual it can give my pluto the intensity I crave and is very satiating though draining. Mutuality is the key for me.
I have been delving into magi astrology and in my natal I have a tight orb rectangle of pluto(virgo 7th), venus(libra 8th),Jupiter and chiron (both in pisces) , sappho (aries). I think this planetary geometry adds to my intensity and obsessive behaviour (on the other hand the positive side is I am passionate and don't just feel - I FEEEEEEL!). I gather also in synastry - Pluto , Chiron and Venus in tight orbs add to the obsessive nature of the relationship. With my natal geometry anyone who manages to form a linkage to any one of those 4 points of my rectangle is going to get the whole package!
Ok, so to continue the conversation, I've been thinking- if however, Pluto is transformation, then is the obsession serving a purpose? Is it a push to transform you? From my experience yes, it's a catalyst. As mentioned above, it's something you believe will make you happier. That's not actually a bad thing.
Also side note, I don't really mean obsession in a stalker-y way, not at all. I don't mean you can't stop yourself from knocking on someone's door!
Maybe it's like a hunger and you WANT TO EAT THAT. Hunger just is.
Just a few more thoughts!
I have obsessed over people before.
Looking back, in my case, it seems like it was a self-esteem issue. So I would have to agree with strawb that the promise of happiness was an issue.
What lessened it was detaching a bit and really looking at what I liked about the person. And realizing that I can build those things in myself.
Then, the obsession either waned (because it was mostly fantasy) or became more of a secret mentor kind of feeling (where the focus is now on me and what I can learn).
But I think there are different kinds of obsessions - yours may be different.
Bumping because I was asked about this.. 
https://elsaelsa.com/astrology/man-with-venus-square-pluto-struggles-to-break-his-obsession/