Honesty: I've never been on a date that wasn't with a spouse. I find the idea pretty terrifying and I'm not sure I'd manage. But in a world where I was supremely okay with going on dates with people...

Tifa
Quistis
Y'shtola (er, just uh, make her human...?)
V'kebbe (ditto?)
Vanille

Rinoa doesn't make the list because as much as she's absolutely gorgeous, I just don't think she'd suit me in terms of relationship material. Ashe, too, because I don't wanna get involved with celebrities/royalty. If I can't 'switch' someone to human then I guess those two can fill in for the Miqote.

For a platonic date (essentially hanging out, I guess)?

Selphie (Seems super fun and accepting)
Vanille (Seems super fun and accepting)
Cid (FFXIV - Just seems like a cool guy to kick back with to talk about whatever)
Guy (HE CAN TALK TO ANIMALS)
Red XIII (I'd love to hear about his race... find out what they call themselves etc)