Negotiations in Persona 5 are a fun concept in theory, but for me, they mostly ended up being an obnoxious hindrance that I could never get into.
Negotiations are entirely dependent on the type of personality that the shadow you’re trying to capture has. There are four different types of personality for shadows in the game. They are as follows:

• Gloomy
  
• Timid
  
• Upbeat
  
• Irritable

You can find out what type of personality a shadow has by looking at the top left during a "Holdup".

It is important to be familiar with what type of personality the shadow you’re trying to capture is. The personality type will be displayed at the top of the screen when you first knockdown a shadow. This will be the only real clue the game provides when you are trying to capture a shadow.
After selecting ‘Lend me your power’ three boxes of dialogue will appear for you to read through. The shadow you’re negotiating with will offer some arbitrary insight that is random and bizarre. Usually it’ll end by asking you a question, and these questions are weird.

They’ll rant to you about young people, ask you what type of foods you like, if you prefer men to women, etc. These questions have no rhyme or reason, and the answers can really reflect that.

The shadows will ask you 2 questions, After you answer the first question, the shadow will then speak another three boxes worth of dialogue and ask a second question.

The second question is the important one. The first question is mostly inconsequential, but the second answer will determine whether or not you capture the shadow. This all depends on the type of answer that you give the shadow.

There are three types of answers in Persona 5:

Good answers: Marked by golden musical notes. This is always the best answer. If you get this for the second question, you will obtain the shadow as a new persona.

OK answers: These are marked by light blue sweat marks that appear above a shadow’s head when negotiating. When you answer the second question with the OK option, you will most likely end the negotiation with an item as a reward. The persona will then flee after giving the item.
However, there is a very small chance, I’ve only had it happen to me once or twice, that the shadow will join you with an OK answer.

Bad answers: Bad answers are marked by red angry dashes. It is okay to get a bad answer for the first question. However, if you get a bad answer for the second question, you will fail the negotiation and the monster will either run away or you’ll have to fight it again. Once you have a party member hit around level 3 - 4 as a confidant, your characters will be able to potentially step in and save a negotiation should things go south.
This ability is tremendously helpful, and it will usually give you a second chance at negotiating with the shadow. Just be sure to get a ‘good’ answer on the second try!

Keep in mind that there doesn’t seem to be any rhyme or reason behind the order that these questions are asked in Persona 5. Each shadow can ask any of these questions depending on the dialect that it uses, and the answer can vary because of that. At the end of the game, I was still running into shadows that were asking the same questions from the start of the game. (The one exception seems to be the more angelic shadows; they speak in a much more ‘matter of fact’ tone that is unique to them. A lot of information is definitely missing on them.) Due to the random nature of the game, the questions here will all be listed in a completely random order. Remember to use the search function! an answer could have 2 diff mood options.

If you see an answer with an out of place question mark or its blank, that means I was unsure with that answer and have not been able to verify it. Best of luck, and have fun! (the questions are in bold and underlined!)
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...You know what I'm getting' at, right? You think you could let me go see my girl?

Nope.

• Good - Irritable

She probably left.

• OK - Irritable
  
• Bad - Gloomy

What kind of girl is she?

• OK - Irritable
  
• Good - Timid

Hey, sonny if somethin's been botherin' you. I'm willin’ ta give you a listen.

My relationships...

• Good - Irritable

My future… (I smell sweaty.)

• Bad - Irritable
  
• Good - Timid
  
• Good - Upbeat

I have no worries.

• OK - Upbeat

Have you made an appointment, ho?

I have.

• OK - Gloomy

That's not it. ?


Just tell me what you know. ?

I wish I could see what kind of parents raised you to run loose and wreak havoc like this.

I can’t show you now.

• Bad - Gloomy

I won’t show you. ?

Leave my parents out of this. ?

Hey, if you got any medicine, lend me some. They’re supposed ta work miracles, right...?

Are you OK?


What kind of medicine?

Good - Gloomy

That won’t change anything?

Good - Irritable


Doesn’t what you’re doing bother your conscience?

Now that you mention it…


Nope.


What’s a conscience?

Good - Gloomy


… Very well. In the place of our Father, I shall listen to your complaints.

Why can’t we end war?

Good - Irritable

No complaints here.


I can’t get a girlfriend.



Out of respect for our Father, let us take a moment’s respite…

If that’s what you want.


What are you telling me?


I’m a minor.

Good - Irritable


...Who the blazes do you think you are?

I feel bad about that.

OK - Gloomy

I’m ME!

Good - Irritable

Bad - Irritable

I don’t have to answer you.



Maybe I should try something new! I don't want to fall into mediocrity, ho...
You're fine as is.

Bad - Gloomy

Good - Timid

Your act is a bit stale...


Time for a makeover.



Hey, if ya got any medicine, lend me some. One of them painkillers…

Are you okay?

Good - Timid

I have some antacids.

OK - Irritable

Good - Upbeat

That won’t change anything.

Good - Gloomy



Hell, I got all sortsa girls lined up if you're into that.

Really?

Good - Gloomy

Good - Timid

OK - Gloomy

You're trying way too hard.

OK - Timid

Good - Irritable

Good - Upbeat

I'm not interested.



How 'bout we have an interview? You're the winner, after all. I'll listen to whatever you gotta say.

I feel great.


I want to aim higher.

OK - Upbeat

OK - Timid

OK - Gloomy

Fighting is pointless.



Hey. So whaddya think when you think about the future?

An average level of happiness.


Live fast, die young.

OK - Upbeat

I just want to enjoy the now.



You carry a gun because you think it'll make you more popular with the girls?

That's right.

Bad - Gloomy

Good - Upbeat

It won't?

Good - Gloomy

It's for self-improvement.

Good - Timid

OK - Gloomy


It's no fun going home when only my annoying mom and dad are there.

Parents are annoying.

OK - Timid

Good - Irritable

You should love your parents.


Make sure you go home.

OK - Gloomy


Me not understand in what way you superior to me...

I'm younger than you./Youthfulness.

OK - Irritable

I'm cuter than you./Cuteness.

Bad - Gloomy

I'm better at small talk./Luckiness.

Good - Upbeat

Good - Timid

Good - Irritable

Good - Gloomy

OK - Upbeat


You go back to your mother's arms. You need take nap now.

I'm not that young.


I'm not sleepy yet.

Good - Upbeat

OK - Upbeat

Mom will wait till I'm done./After I’m done with this.

Good - Timid

Good- Irritable


Now, people don’t even know who lives next door to them. Shouldn’t we know our neighbors better?

It’s saddening.


I don’t really think about it.

Good - Irritable

Privacy is important.



I insist you surrender yourself to the authorities.

This is a misunderstanding.

Good - Timid

I don't have the time./I apologize.

OK - Gloomy

Good - Gloomy

You've got the wrong idea.

Bad - Gloomy

OK - Irritable



But is it fair to the others if I find this happiness, leaving them all in the dust?

I think it’s fine.


What’s wrong with that?


You’re too self-conscious.

Bad - Gloomy



I occasionally wish to pamper myself as a reward for working hard. How would you do that?
Relax at home.

Bad - Gloomy

OK - Upbeat

OK - Irritable

Go impulse shopping.

Good - Gloomy

Don't be so selfish.



Why're you so desperate?

I don't want to die.

Good - Gloomy

There's something I must do.

Good - Timid

OK - Gloomy

I'm not desperate./I want girls to like me.

Good - Upbeat

Good - Irritable

Bad - Irritable


That's whack, man. Maybe you should get your head checked out.

I probably should.

Good - Gloomy

I'm fine as is.

OK - Timid
Good - Irritable

You're a sore loser.

OK - Upbeat


Care to explain yourself? I certainly hope you have a good reason for this boorish treatment.
It'd take a while to explain./That would take a while.

Good - Gloomy

Good - Timid

There's no need to explain.


Just shut up./Just shut up...

Good - Irritable


Why have you decided to be more communicative with me?

Your looks.

OK - Gloomy

Good - Timid

You seemed useful.

Good - Gloomy

Bad - Timid

No particular reason.

OK - Timid


...So? What's going to happen to me now?

You'll be killed.

Good - Irritable

What do you want to happen?

Good - Upbeat

It's a secret.

Good - Upbeat

Good - Gloomy



Do you have a dish you’re good at?

Fried rice.

Good - Timid

Spaghetti carbonara./Mystery meat.

Good - Upbeat

What are you saying?



What’s gonna happen to me?

I’ll make mincemeat of you.

Good - Irritable

I’ll play nice.


I’ll be your dominatrix.

Good - Upbeat


I wanted to go on vacation, too, before all this happened...

That's too Bad.


What are you getting at?

Good - Upbeat

You have a boyfriend?

OK - Upbeat


...I'm not going to go easy on you for doing something like this, you know...
I'm sorry.

OK - Upbeat

Bad - Upbeat

Good - Irritable

Prepare for the worst.

Bad - Gloomy

How much do you want?

Bad - Irritable

Good - Upbeat


You do understand that I'm here because people like you exist, right? (You do understand that we are here because of people like you, right?)

I never thought of that.

Good - Irritable

Good - Timid

Eh, doesn't matter./I understand.

Bad - Upbeat

What do you mean?

Bad - Upbeat


But this way of life in this world is all I’ve ever known.
It’s not meaningless.

Good - Timid

There are other ways to live.


You had a good run

Good - Gloomy

Confess your sins.

I apologize.


I think… I was wrong.


No chance.

Good - Irritable

You, who reside in that world of the almighty, what is it that has beleaguered you so?

The world is almighty?


I’m not beleaguered.


My “dad” isn’t almighty.

OK - Irritable

C’mon, what’s with the mask? Kinda cringy, don’tcha think?

Sure is.


Shut up…

Good - Gloomy

I’m secretly a kid.

OK - Timid

C’mon, what’s with the mask? Kinda cringy, don’tcha think?

Sure is.


Shut up…

Good - Gloomy

I’m secretly a kid.

OK - Timid


It is to become aware of the gaze of our Father who watches over you with loving grace

What are you talking about?/I don’t understand.

Good - Irritable
OK - Irritable

I feel his gaze.


I don’t think so.


Can you sacrifice yourself in order to demonstrate your adoration of our Father?

I can. ?


I can’t. ?


I don’t adore him.

Good - Irritable

I wonder if us speaking together like this now means that we are somehow connected...
Eh, could be./It could be.


No, I don't think so./No way.

Good - Irritable (R)at

OK - Gloomy

It's what we call destiny./It’s fate.

Good - Upbeat

What you thinking now?

I have homework tonight.

Good - Timid

I need a new cell phone.

Bad - Gloomy

OK - Irritable

I want girls to like me.

Good - Gloomy

Me guessing you have power that me not have. But what is it...?

It's my intelligence./Academics.

Good - Timid

Good - Irritable

It's money./Empathy.

Good - Gloomy

Girl power.

Good - Upbeat

OK - Timid

Humans always want either an autograph or a self-hee, ho. Which is it, ho?

I want an autograph.

Bad - Gloomy

OK - Timid

I want a photo.

Good - Timid (?)

Give me your credit card.

Bad - Timid (?)

My only choice now... is to retire, ho.

That's too far.

OK - Upbeat

What are your plans?

OK - Gloomy

You had a Good run...

Tell me, what does “equal footing” mean to you?

Not talking down to people.

Good - Timid

Sharing household chores.


Splitting all the costs.

...I gotta ask. How do you train?

I don't really train.

Good - Irritable

Good - Gloomy

I just have a knack for it.

OK - Gloomy

Bad - Irritable

Luck's usually on my side.

OK - Timid

Good - Upbeat

In the end, killin' me's just a waste of yer time and energy. You get what I'm sayin', right?

When you put it that way...


It's not a waste.

Bad - Irritable

Enemies must be eliminated.

Life’s nothing but pain anyways. Just do whatever you want.

You should have stayed home.


You won’t die easily.

Good - Timid

Don’t get desperate.

There are obviously hundreds more interactions that would simply take WAYYYYY too long to put in the guide but hopefully you have would have a full understanding by the time you reach this part to do negotiations on your own. Thank you so much for reading and have a good one.