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Anyone who has questions about Strider - I am a similar font of knowledge.

can confirm, geoduck is jello's favorite of the options provided, but not his favorite food in the whole world

It does vary. I got my first Jello with "someone has to pay the bill" as final option. The way I imagine the game to work is each answer has a hidden point value assigned to it, and you need to reach a certain total to get the companion, whereas a slightly lower value will earn you one of their other items instead.

I will certainly take you up on that offer. Strider is the best date ever!

you would be partially correct. this is, in fact, one of the ways that prizes are determined, so you have some wiggle room if you don't do things perfectly! however, strider is the keystone example of a date where you have to pick the correct choices.

jello is points based.

Oh, I thought it was all just random.

Bro, if it was random I wouldn't be suffering this hard
/kisses my 3 Jellos

there's a level of randomness as well

so

there are 3 prize tiers. best is the companion, worst is the shared pool of rejection items

in the middle, each date has their unique equippables, like jello's collar and albert's book. which of their equippables you get from the list is random, but if you're getting equippables at all, that means you're not on the right track to get the companion and have to alter your path/look for more positive choices.

I see... so... does that mean I can still get Albert's suit?

albert's equippables are his book and his riding crop

Oh... I thought there was more.

I don't seem to be able to get Strider's cave, even following the guide mdom so kindly made. Maybe it's also semi-random?

I'll try to do a more detailed one... please, hold while I go smooch the spiderman.

Strider's Warm Legs is not on the list yet.

and what are the details sis

Serra, I added more steps!! Hope it works for you!

...lemme replay again.
-edit-
ok replayed to double check.
I think u have to be nice, ask about his mothers, then choose mediocre answers (which are ones that are not instant death, but not exactly stellar either). Being nice then mean again after the mother part also works.

Oh gosh...I got 2 of the warm legs, but I legit forgot to keep track of how I got them.