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Suuuuuuuuuper late with this question m̶a̶i̶n̶l̶y̶ ̶b̶e̶c̶a̶u̶s̶e̶ ̶i̶t̶ ̶t̶o̶o̶k̶ ̶m̶e̶ ̶a̶ ̶w̶h̶i̶l̶e̶ ̶t̶o̶ ̶f̶o̶r̶m̶u̶l̶a̶t̶e̶ ̶t̶h̶e̶ ̶a̶n̶s̶w̶e̶r̶ ̶f̶o̶r̶ ̶t̶h̶i̶s̶ but Elio doesn't truly recall a "best" nor "worst" date since those things are subjective and they were more like hangouts to keep his close friends/partners company than romantic outings.
Best:
They weren't officially dating yet but Marcie bringing Kingston along to the pokemon she volunteers at (aka a good excuse to see him play with baby pokemon and see if he's father material) it was Marcie sharing something more personal/meaningful with Kingston and because she can be quite guarded with people the sign of trust in letting him into this side of her also meant a lot to him. It was that and seeing Marcie, sweaty and messy-haired in an old shirt sweeping up bits of poke-kibble from the floor that first made K seriously consider "oh I am in love" because it was deeper than the physical intimacy or attraction he'd experienced up to that point with her (and in past relationships with other people.)
That or after they'd been dating for a while and considering moving in together, they went to a department store and window shopped for potential pieces of furniture they needed to pick up, but it turned into them trying to describe an ideal home with each other. When Marcie leaned over a baby crib and teasingly asked if they'd have space for it she was surprised when Kingston answered 100% seriously that they could use the larger spare room for a nursery instead of a home office. Having that affirmation in knowing they have the same priorities in wanting to make a family together made Marcie treasure that memory since she's always wanted a normal family of her own and she really felt like she could see a future with Kingston.
I haven't even gotten to the worst dates RIP me
Uhhhh worst date for Kingston: having to sit through a very awkward arranged marriage meeting, made more awkward because the other party caught him trying to ghost the meeting even before it started.
Best date for Yorra was hanging out at the rooftop of some half-finished building with Emille and a box of alfajores between them. Also happened to be their very first date even though neither called it that at the time.
Worst was when she brought a random guy home and he cried after sex cuz he missed his gf LMAO
Already explained the worst, so here's the best: Clair surprised Tyler by inviting him to a date in Ecruteak City and they had a good time sightseeing and eventually watching the Kimono girls in the Theater. However, Cloud was enamored by the Eevee evolutions perform on stage, so he ran on stage to perform with them. So of course Tyler and Clair end up running over to try to grab him, but the Kimono Girls, quick thinking as they were, dragged them on stage to help perform a play about a heroic leader saving Ecruteak town from the blazing fires. It was definitely embarrassing, but both Tyler and Clair had an amazing time, and afterwards, they helped Clair give Tyler some fantastic chocolate
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