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Melancholy 

To be 'melancholy' is a brand of sadness that is over thought, prolonged and can be caused by any reason regardless of its the magnitude. It's a very personal, heavy weighing sadness. It has similar characteristics with depression however, melancholy is an insidious sadness. It's more than simple desolation or dejection, melancholy feeds on pensive self reflection in such a low state, reflecting lower and lower on itself until you can't see anything other than sadness.
Example 1)
Person 1: I just went for a 5 hour walk, didn't bring any food or water and just listened to music.
...
Person 1: It's 3 AM... maybe I'll just eat tomorrow.
...
Person 1: ... fuck I need to stop thinking about this so much, it's making me Melancholy.
...
Melancholy by Slerbo October 19, 2013

anal melancholy 

The sadness expressed by the anus the morning after a euphoric spicy meal containing chillies.
I am experiencing such anal melancholy after last nights curry.
anal melancholy by jadw August 23, 2009

Melancholy Masochist 

Noun: A man who constantly subconsciously pursues women who are unattainable or more so not girlfriend material at all. And through this process suffers heartbreak repeatedly due to the combination of lack of self confidence, paranoia, the need to please and on the females part and outstanding combination of mind games, misread-able flirting and leading on. Broken at that point the man continues to pursue romance with another similar candidate as the previous as if he enjoyed the pain.
Ex: "Aww man David likes Jane?! He's such a Melancholy Masochist, she's gonna fuck him over just like Tina, Molly, and sandra did. and then he's gonna break down and do it again.

Melancholy 

Melancholy is a feeling of bitter sadness. It’s usually seen as a more in-depth emotion, with strings attached. People who suffer from depression may feel melancholy often. It can be used as an adjective as well.
Adjective: Her melancholy smile seemed to hold more than just resentment.

Noun: A feeling of melancholy bathed the island in its gloom.
Melancholy by typicalcabbage_ June 15, 2020

discombobulated melancholy 

A discombobulated melancholy is a long-lasting depression.

Melancholy is usually used as an adjective, but it becomes a noun when combined with the word discombobulated. It's often associated with emos.
Adult: "I don't get it, why can't you just hang out with other kids, have fun?"

Emo kid: "I'm suffering from a discombobulated melancholy. Just leave me alone."

Melancholy 

When I go to the bar alone which me and my old friend used to go to together, these bitter sweet memories are making me feel melancholy.