Mexancholy 

A feeling of excruciating agony resulting from utmost self awareness and pensive, meticulous analysis of the future, your purpose, and your absurd existence; a process that is occasionally followed by a traumatizing despair that requires further rumination, thereby engulfing oneself in a loop of existential anguish, dread, and sempiternal desolation.

He's constantly disturbed by overthinking his life purpose too often; I think that such a mexancholy is inevitable.

Mexancholy by linguistic vlogbrother January 28, 2018

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 Masochist by the pain of atlas January 21, 2010

Melancholic 

Extremely fucking sad

“Im feeling melancholic today”
“Wow it’s ok”

Melancholic by Fullofglee February 28, 2020

Happily Melancholic 

Happily Melancholic is the feeling of being happily content with life but you are secretly sad and lonesome as well. Not really, depressed because you are ok or have come to terms with your feeling of sadness but you're not always sad and depressed.

*Ways to know you're Happily Melancholic*
-Lost A Close Loved One
-Really Good Worker
-Distant (from others)
- Loveable towards people.
- Can't Trust others well.
-Have problems with making close friends.
-If you're really creative or you read a lot.
and so on..

Guy #1: Are you Happily Melancholic (or HM)?
Girl #1: No, why?
Girl #2: Because you listen to Maria Taylor, Dido, Gemma Hayes, and the only japanese music you like is Akino Arai. I told you that the music you like would make people think you're "HM".
Girl #1: Hmm, I guess you're right.

Happily Melancholic by HappilyMelancholic July 12, 2010

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