I don't normally do the game-generated, goal-oriented dates, so I just have people get together and interact at venues. I like downloading different venues from the gallery to give my sims more options.
An amazing lounge...the pictures don't even do it justice:
https://static.wixstatic.com/media/01c58f_f45a9593caeb422891b383be9233a6c8~mv2.png/v1/fill/w_740,h_457,al_c,q_90,usm_0.66_1.00_0.01/01c58f_f45a9593caeb422891b383be9233a6c8~mv2.webp
https://static.wixstatic.com/media/01c58f_1f30cac41d2a41f09cfa6fb65c4003e9~mv2.png/v1/fill/w_740,h_457,al_c,q_90,usm_0.66_1.00_0.01/01c58f_1f30cac41d2a41f09cfa6fb65c4003e9~mv2.webp
I also found this fun Cheers-like bar:
https://static.wixstatic.com/media/01c58f_90798c4e070f4319aa00e9b737c4698f~mv2.png/v1/fill/w_1553,h_1024,al_c,q_90/01c58f_90798c4e070f4319aa00e9b737c4698f~mv2.webp
I've had my sims go to ice rinks, but only go if the sims already have some skating skill, otherwise it's just an embarrassing amount of tumbles, haha. If it's snowing, they can build a snowpal together. Movie theaters are nice, too, but it's best to just have one theater and no other seating in the lobby so that they're forced to at least sit in the same room. Sometimes I'll temporarily move the sim I'm dating into the household so that I can control them both while they're on the date, and sometimes I'll just do a normal date where I only control my sim.
I try to pick a venue that fits their personality. Like, my sims was dating a down-to-earth guy and a sophisticated guy, so the down-to-earth guy took her to a cafe, and the sophisticated guy took her to a really posh lounge.
If they're ready to make a commitment, I'll send them to Granite Falls for a weekend trip.
As for what I have them do, I just have them do whatever there is to do at the venue, and on top of that, talk, flirt, hold hands, and kiss.