Best Dating Movies & TV Series of the 1990s

Our pick of the 22 best dating movies and TV series of the 1990s to stream on 3eyedraven, sorted by weighted rating and refreshed as scores move. Cast, ratings, trailers and streaming options included.

Good Will Hunting 1997 ★ 8.2

Eat Drink Man Woman 1994 ★ 7.6

Sex and the City 1998 ★ 7.4

Will & Grace 1998 ★ 6.9

Jack & Jill 1999 ★ 7.6

Dream On 1990 ★ 7.0

In the Company of Men 1997 ★ 6.7

Caroline in the City 1995 ★ 6.6

The American President 1995 ★ 6.5

Double Happiness 1994 ★ 6.5

Fever Pitch 1997 ★ 6.5

Jawbreaker 1999 ★ 6.4

Big Girls Don't Cry... They Get Even 1992 ★ 6.1

Entropy 1999 ★ 5.9

Can't Hardly Wait 1998 ★ 6.2

Next Stop Wonderland 1998 ★ 5.9

A Thin Line Between Love and Hate 1996 ★ 5.7

Mannequin Two: On the Move 1991 ★ 5.8

Virtual Sexuality 1999 ★ 5.3

Buffy the Vampire Slayer 1992 ★ 5.6

'Til There Was You 1997 ★ 4.0

Bimboland 1998 ★ 4.4