The personality is the type of answer they want. Irritable wants serious answers

Upbeat
Likes: Funny
Dislikes: Serious, Vague

Timid
Likes: Kind
Dislikes: Vague, Funny

Irritable
Likes: Serious
Dislikes: Vague, Kind

Gloomy
Likes: Vague
Dislikes: Serious, Funny

If you know they're names, you can usually tell their personalities based on what they are in mythology and their moral alignment. It might be different for p5 but that always helped me in smt games

In my experience, when in doubt, pick the top one.

With Upbeat Personality
These Hold-Up dialogues are used by Persona with an Upbeat Personality. “Me may not seen your true intentions because a mask covers your face. What are you thinking now?”
Reply: I want girls to like me.

“The more me look at your mask, the more strange it look. Why you wear mask to fight, anyway?”
Reply:

“Me thought you not from around here. You human? Why you come all the way here?”
Reply:

Me admit it. Me afraid of dying now, all of sudden. You can laugh at me if you want. You had something you lost, and you not know how important it was until after it gone, right?”
Reply:

“Me not understand...How did human outsmart me? Me not understand in what way you superior to me...”
Reply: I'm younger than you.

Me know humans take joy in raising descendants, your future generation. So me have to ask...You given much thought, what if you go to place where you could die at any moment?”
Reply:

“After me looking closer, me can see you really young human. You not even alive that many years. Why you fight and put yourself in harm's way?”
Reply:

Your victory pretty much assured, so me want to ask deep question. You have wishes you not can let go of, even after you die?”
Reply: I want world peace.

With Timid Personality
These Hold-Up dialogues are used by Persona with an Timid Personality. “Ain't you kinda old to be playin' dress-up? So, who're you tryin' to impress with that mask?”
Reply:

“...Y'know if you think about it, I'm basically your senpai. Just thinkin' about hierarchy...You should be showin' me a little more respect, shouldn't you?”
Reply:

“...Um, why're you goin' for me? Ain't there worse people out there? What kinda guys piss you off?”
Reply: Loud talkers...

“Hey, you doin' this just 'cause our eyes met or something? That's wack, man. Maybe you should get your head checked out.”
Reply: I probably should

“Yo, you can't just waltz around here like that. You're violatin' the weapons code or whatever, man.”
Reply:

What's gonna happen to me?”
Reply:

Agathion
“Oh, yeeeah! I wanted to ask you, mister, 'cause maybe you would know why...It looks boring to me so how come grown-ups like kissy facing? What do they like “making out”?”
Reply: How should I know?

“...Oh, in the mail, I got a letter with my name on it, but it was from someone I don't know. What was that, anyway?”
Reply: A love letter

With Irritable Personality
These personality dialogues are used by Persona with an Irritable Personality.

Bicorn
“...Y'know, up till now, I did whatever I wanted. I knew it was gonna catch up ta me someday. If yer gonna kill me, do me a solid and make it quick.”
Reply:

“Y'know, before I died, I wanted ta take a trip somewhere...How 'bout you, sonny? What kinda trip do you wanna take?”
Reply:

“...I gotta say, you've been a pretty inconsiderate host. You oughta show more hospitality. Couldn't you at least make me a cup of tea or somethin'? Hell, that's be real polite.”
Reply: I don't have any.

“Hey. Yer kinda skinny, ain't you? These days, I hear even men go on diets too...What do ya usually eat?”
Reply: Vegetables

With Gloomy Personality
These personality dialogues are used by Persona with an Gloomy Personality.

Jack o' Lantern
“...Hee-ho, are you here to interrogate me? Have you made an appointment, ho?”
Reply:

“I'm tired of the endless fighting, ho...I need to recover, ho. Don't you feel that way too...?”
Reply: Yeah, sometimes.

Silky: Not recruited yet.

I don't know yet if some Persona of different Personalities reuse certain quotes. Based off that. I may compile a list of what answer's resemble serious, funny, vague, or kind.

You can see the name of some Persona's and that is because some personas have their own quirks...Like all Jack's have hee-ho in their dialogue.

If you see a dialogue option that you know the best answer too, please fill in the blank and I will compile it to my info. I'd like to make this a walk-through on GameFaqs. Getting Persona's to like me in the original Shin Megami Tensai games was a B**** and I never find guides like this. So I wanna make the world a better place.

Demon negotiations are meant to be frustrating you fool

Yes, I am a WorldsFool.