Keyword: romance oldest first

Games found: 12.

Romance is not a common theme in video games. Sex is, as in movies and other media, but romance? It's prominently part of a few visual novels and is one of the main themes of the Leisure Suit Larry series. Not much else.

Leisure Suit Larry 1: In the Land of the Lounge Lizards

DOS1987 Sierra On-Line 4.2
Leisure Suit Larry 2: Goes Looking for Love (in Several Wrong Places)

DOS1988 Sierra On-Line 4
Romantic encounters at the dome

DOS1988 MicroIllusions 3.8
Leisure Suit Larry 3: Passionate Patti in Pursuit of the Pulsating Pectorals

DOS1989 Sierra On-Line 4
Leisure Suit Larry 5: Passionate Patti does a Llittle Undercover Work

DOS1991 Sierra On-Line 4
Leisure Suit Larry 6: Shape Up or Slip Out!

DOS, Windows 3.x1993protected Sierra On-Line 3.7
True love

Windows XP/98/951995 Spectrum Holobyte 4
Leisure Suit Larry 7: Love for Sail

DOS, Windows 3.x, Windows XP/98/951996protected Sierra On-Line 3.8
Season of the Sakura

DOS1997 JAST USA 4
Fatal Relations

Windows XP/98/951998 3.9
Three Sisters' Story

DOS1999protected JAST USA 4.1
Broken Sword: The Shadow of the Templars

Windows XP/98/95, DOS2009protected Revolution Software 4.1