My friend and I watch SATC and High Fidelity (2020) whenever we want to feel better about our romantic (and just general life choices).
If you like the world of Gilmore Girls, Freaks and Geeks is so comfortable to sit in. The characters feel like how real high schoolers (I dated a guy in high school a lot like Nick from this show and we all have, I think). The costuming and soundtrack is great, the midwestern vibes are comforting, and the acting is surprisingly raw and realistic for being a comedy series. Martin Starr has genius comedic timing.
Dollface is kind of a hidden gem! Kat Dennings is a gemini queen and she creates a really lush and intricate imaginary world in this show.
Community is perfect for pop culture nerds- the first season is like a lot of sitcom shows in that it takes a bit for them to hit their stride and find their audience. It does not use the mockumentary style like Parks & Rec and The Office, which gives the show more permission to be weird and far-away from reality.