The Brief: "Depresso espresso" is an internet term used to express feelings of sadness combined with amusement.

Bluesquiggle
DEEP DIVE

A depresso espresso is not an actual coffee drink, but a situation that is both depressing and funny. Since the phrase both rhymes and mentions depression, it combines silliness and sadness. “Depresso espresso” is a popular caption for bittersweet memes and social media posts.

According to Urban Dictionary, it means “a feeling of being sadness but you also have a good sense of humor.” Another variation is “More espresso, less depresso,” which alludes to drinking caffeine to relieve feelings of sadness or depression.

https://spideyandstark.tumblr.com/post/175443537234/peter-%E1%B5%98%E1%B5%90-%E1%B6%A6%CB%A2%E2%81%BF%E1%B5%97-%E1%B5%97%CA%B0%E1%B5%83%E1%B5%97-%E1%B5%97%E1%B5%92%E1%B5%92-%E1%B5%90%E1%B5%98%E1%B6%9C%CA%B0-%E1%B6%9C%E1%B5%92%E1%B6%A0%E1%B6%A0%E1%B5%89%E1%B5%89-%E1%B5%90%CA%B3-%CB%A2%E1%B5%97%E1%B5%83%CA%B3%E1%B5%8F

Depresso Espresso from meme