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Super_Boom said:

I got with Yukiko on my sole playthrough, though mostly because I got caught up in the game and my relationship seemed to develop faster with her. Honestly I can't even remember much of her story now, so I kind of regretting not getting with Ai or Rise, who had much better (and memorable) stories. I'd probably date Ai on my 2nd playthrough, if that ever happens.

You can actually date multiple people at once. I maxed out all of the playable characters' social links, so I could have dated all of them, but I just went with Yukiko.