I recently sent a teen on a date with another teen to Sunset Valley's recursive strand (yeah, not much objects there). It landed as a great date!
I had the male, Frank, take a baseball, foot-and-hand ball and a flying disc with him to the location, filling up his needs before arranging it on a saturday morning (about 9am). On the way there, I sent the household's witch, Rena, to the same location behind him, to start with Frank's RI, Rena (no not the same person, Alvi as opposed to Lanford). Note that Frank has the Hopeless Romantic trait while Rena Alvi has the Inappropriate trait (which is how they became RI's right at the relationship midline level, which doesn't seem that bad to me).
Here's where the fun starts: I initiated a few hours of catch with the baseball then another few with the disc. Midway through, I initiated a series of flirts and makeouts, stopping at the end of that for Rena Lanford to fill Frank's Hunger up. After that finished, I had the two watch the stars together (though it was short-lived) and then a few more makeouts before ending it. As mentioned at the top, all of this resulted in a great date and since I didn't do a date for a whole generation before Frank, I was surprised to achieve that.
In short, be prepared and take care of those needs BEFORE the date is started.
