I could have sworn High School Years added some sort of dating app but I obviously didn't play the pack enough so I'm not sure where I got that from... (no I don't have any mods like this). Just checked in-game and I'm not really finding anything like it so yeah don't mind me. heh
You could start a singles club with Get Together. Make the club member requirement Marital Status : Not Married. If it were my game I would choose any fitting lot like a bar and add the Romantic Aura lot trait. Set this lot as the Club Hangout. All kinds of Club Activity options to make it really spicy. >:) Now I might have to do this. I could see things getting out of hand fast and that's ok. A little chaos is always entertaining.