The Jackbox Party Pack 4 (EP)

You can get this and Monster Seeking Monster: Mob Rule in the same game. A minimum of 4 Players and 1 one Audience is required if you are doing both. If you are doing just this trophy, no Audience member is needed.

You need to play through one round with no Player going on a successful date. A Player can get asked out, but they need to be rejected. It is easiest to just let the game idle for about 2 minutes. Have no one chat with anyone and no one choose anyone to date. Since no one chose to go on a date, the round will end and trophy will unlock.