1.) A state of mind where one mourns the loss of the freedoms and/or temporary relationships of summer.

2.) This song is sung by Lana Del Rey
Scenario 1:

Girl (with her head against the window)

Friend: "what's the matter? You've been like this since September."

Girl: "I don't know... I guess I just have that summertime sadness."

Friend: "I know what you mean: I wasted mine, too, and I wish I could get it back."

Scenario 2:

I got that summertime,
Summertime sadness.
S-s-summertime,
Summertime sadness.
I got that summertime,
Summertime sadness,
Oh, oh-oh-oh oh-h...
by The Quiz-Trivian-Naire October 21, 2013
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The feeling of getting bullied at summer camp and then getting punched in the face afterwards. Another bad thing that happens is getting bullied online by the same people from camp.
Me: I experienced summertime sadness because I got brutally punched in the face.
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A:Hi, I'm a Lil' Fucker
B:What's your favorite song?
A:Summertime Sadness Remix, perfection
B:Fuck you
by Lunudelflop August 31, 2020
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