I looked around on Steam and there didn't seem to be a Steam hosted guide for Judgement's eligible bachelorettes - in other words, a dating guide - so I decided to write one up. Before I get into the four girls that you can date in this game, there are a couple of preface things to take care of.

The first thing to note is that performing this side-activity will grant you three achievements:
A girl revealed their true feelings.

Two girls revealed their true feelings.

Four girls revealed their true feelings.

Yes, there are only three achievements, not four (one for each girl). They specifically unlock after the girl has confessed her love to you regardless of you accepting it or not.

It should be noted that for some of the date activities, there may be cats which are required for the achievement "Look, A Cat." I will call these out.
Lastly, some of these girls are only available after completing a specific task or achieving progress in the main story. They will be presented in the order that I came in contact with them.
While frowned upon in real life, you can date all four girls simultaneously and go steady (accept their confession) and the game will not punish you in any way outside of some text that tries to make you feel a bit guilty. I will leave whether or not you date one or all four to your discretion. May as well have a waifu war in the comments, who's your pick?

The expected gameplay loop is as such. You are introduced to a girl at a point in the story or during a side-investigation (substory). That girl gives you her number. You can proceed to text her and then invite her to meet up. You meet up and can present a gift or, if you have it, an alternate outfit which you can request them wear on a future date. From there you choose an activity. This does depend a bit on how far in the story you have unlocked. You can go play darts, go to the batting cages, or go gambling at the Casino. Once done, you will sit down and talk, this is where a majority of your affection meter for the girl will be raised. Once the date is done, she'll text you. After some time, she'll text you again (usually a few minutes, so get into a few fights or something) and you can finish up the date officially and some time later (more fights to pass the time), you can text her again to set up another date. Rinse and repeat 4 times and she'll confess to you where you can accept or reject her love. Regardless of what happens, you still get SP.

While not required, some things you'll want to expedite the dates to the next level are the following:

• Gifts (each girl is different), but you will want 3 per girl; 12 total
  
• Texting her "right" (picking the most appropriate but pro-story choice)
  
• Picking perks that increase affection gain from texts and gifts
  
  
• Winning the activities

This is easily accomplished without as long as you pick the right choices but it is highly advised to stack the odds in your favor.

It is highly advised to save before the date just in case you either choose the wrong choice OR miss a cat if you're going for the "Look, a Cat" achievement in this playthrough of your save file.

Sana is the first girl that you will encounter in the game for the girlfriend side-story series. The only requirement she has is to complete part of the main story until you encounter her in Theater Square and complete the single side case "Amidst a Dream." Once done with the case, she will contact you. Reply with "I’ll cheer you up anytime."

Make your way over to Theater Square where she performs on the east side of the beer garden. Interact with her and when she asks if you came to see her perform, reply "Of course." The interaction will end and she will message you again, reply with "I expected nothing less of you." Now that is done, she will ask to meet up with you. The true dating game begins.

The thing to keep in mind with Sana when choosing gifts is choosing those that are geared towards "young women." Avoid those that are geared towards "mature" or have "extravagant" in their flavor text. If you have the unlockable alternate outfit, you can gift that to her as well at any time during the dating interactions, but it will not give any intimacy boosts.

The activity that you'll want to do for Sana is going to the arcade and playing the UFO Catcher minigame to win the dog plush she wants. Doing so and winning grants a massive intimacy boost. Once the activity is done, you will go to a cafe to talk.

Gently express concern

I’m actually pretty big on curry.
Playing pinball.

Younger
15 Years

Choose the option to take a selfie with her and end the conversation. The date is officially over. Now, before you can unlock the next date, you must do the following:

• First, respond positively to her texts to you.
  
• Second, when she becomes available to be viewed in Theater Square to listen for her performances.
  
• Third, when she messages you that one of her songs is getting released soon you can then invite her out for a second date.

Once the date begins, you will receive an LP from her as soon as the date starts named with the namesake of the case you had with her: "Amidst a Dream." You may play this at any time from this point forward in your office. You may choose to give her a gift now and choose a date spot. Before you can leave, you will be confronted by a "passionate" 'fan of hers. After this, you may invite her to your office to continue the date.

She will proceed to make you something to eat, when given the option, choose "Sing Her Praises." From here, the conversation portion of the date will proceed.

(There are no response options, just choose it).

You must have some real talent.

That’s a relief.
Still single. (If ever you already have a different girlfriend at this point, there's no negative consequence for choosing a harem route as mentioned before).

Choose the option to take a selfie and end the conversation. The date will end and you will escort her back to Theater Square. There will be a cutscene with some foreshadowing and the date event is officially done. It will be a hot minute before she responds to you, so do some activities before she texts you again.

For this date, before meeting up, you may wish to complete the friend mission for the Le Marche owner. Doing so, you will get a suit as a reward AND you will automatically wear it for this date as you wilil both be in disguises. You can proceed to give her another gift and choose a dating activity of your choice. Once done, you will return to your office to do more conversations.

I like them both.

That is a problem indeed

Pretend you know who it is

Choose to take a selfie and end the conversation. The date wiill end and as you escort her out, the stalker shows up in the shadows, foreshadowing of things to come in the next section. As previous, continue to text her until the prompt to invite her for a date again shows up.

There's nothing really important to note other than she'll be wearing a disguise. Choose to give her a gift or not and then choose a date activity. Once done, you'll be at your office again.

I still want to see you.

(There are no responses that need to be chosen).

I see you as someone special.

Take a selfie and end the conversation. There will be two more dialog options to choose, they are "Follow your heart" and "What about that song you wrote?" The date at this point is over but the event is not. After she leaves, you will get a prompt from Tak thinking that he should check up on her since she hasn't returned yet. Head over to Poppo on Showa where her icon is at. You will see that she is being harassed by her stalker. Beat the snot out of him in whatever preferred style or EX finisher you want. He'll leave and you'll exchange a few more texts with her. Reply with gusto/enthusiasm.

And now we are at the capstone of the relationship. Once she's ready, she'll text you asking to meet up. Agree. You will meet in your office. Unlike with some mainline story events, you won't be forced into this and there will be a circle placed on the floor with a prompt to wait for her.

Once she arrives, exhaust all of the conversation topics, reserving "(She mentioned something important…)" for last. Once selected, a fully voiceacted cutscene will take place and she will confess her love to you. If this is the first girl you've dated, the achievement "Going Steady" will unlock. As mentioned before, the game doesn't care if you have multiple girls (though Tak will throw some flavor text about feeling guilty if he does have more than one girl) or not. Accept or decline, I'll leave up to you to decide on.

Nanami is likely the second girl that you will come into contact with as you complete the main story. The only thing you need to complete in order to unlock her as a potential love interest is completing the side case "Smart Watching." Once done, she will text you a few times with some spacing, so just keep doing activities until the prompt to ask her out appears.

The gifts that you can choose for her are those geared to mature women or stuff that's "stylish" but not overly expensive. You'll meet her at Theater Square and after you do your date activity, you'll go to the bar to talk.

There are some setup replies, chooses "I’m glad that stalker of yours is gone." and "Tell me a little about yourself."

I'd have to agree.
Well said.

Actually, same here.
Yeah, I do.

You look young for your age.

After the date, you will be introduced to her bestie, Yukko. You will become very acquainted with her during this dating side story. After this, keep responding to her texts and she will want to go out again.

Meet the girls at Theater Square. You will NOT be able to give a gift and you will be forced to play Darts as the date activity. Once the activity is done, you will sit down with the two of them and start the conversations.

Respect can’t be handed out to just anyone.
Do you not like the concept of dating?

It was when I first saw Nanami-san.

I’m very interested.

There will be no options to take a selfie this time and the date will end here. You will get Yukko's number and you will be needing to text her in order to complete this dating side story. Some time will pass and Nanami will contact you herself. Ask to hang out just the two of you. Yukko will contact you, just complete the text thread and she'll ask you to meet up at Wette Kitchen on West Taihei. Agree to the plain to trick Nanami. After speaking to Yukko, text Nanami and ask her to help you with your "investigation" and she'll jump at the opporitunity. Meet her near the Dragon's Palace with the icon on the map.

This is considered a date and you can give her a gift before the "investigation" kicks off. There will be a conversation after it is complete. You will then be prompted to tail Yukko. Of all of the tailing missions, this is the easiest. You don't even need to hide at any point. There is only one prompt that you need to do, and that's when you reach the first red/orange box and you're prompted what to do, choose to "hold her close." You will do a second set of tailing which takes you to the M Side Cafe where you can now have a conversation with Nanami.

I wonder.

Take a step back and apologize.
But can you see me as a love interest?

I’m sorry you had that experience.
Is that why you haven’t had a boyfriend for a while?

You may now take a selfie with her and end the conversation. However, the date isn't quite done yet. Yukko will start to stare at you in order to get you to do something with Nanami, choose the option that gets you more physical. Have her feed you. Now, the "investigation" is complete but there is one last choice before the date is fully over. Choose "I'd rather investigate some things we can do together." Now the date is over.

You will get some more texts from Nanami. Select any option and Yukko will also contact you, answer her and contact Nanami again until she agrees to go out with you again.

Before you go on this date, you may wish to unlock the drinking perks to drink more than her as you'll go to Bantem after whatever activity you choose. You'll meet up with Nanami in Theater Square again. She'll come dressed differently this time. Choose "I think you look fabulous" and proceed to give her a gift and choose your preferred dating activity. After this, you'll go to Bantem and suggest to do a drinking contest. The more questions you ask, the drunker you get so having the perk definitely helps keep up with her.


Tell her companionship is important.


Try to compliment her.


I wouldn’t mind eating something you made.

You like older men.


After the drinking game is done, choose "Could you ever see me as a boyfriend?" After this the only thing left to do is to take a selfie with her and end the conversation. The date is officially done. You will leave Bantem and your ruse with Yukko is discovered. At this point, just come clean. Now you'll need to suffer through ghosting. The timing of this is the most annoying part of this entire side story.

Flip between Nanami and Yukko for text conversations. Eventually, you'll reach a point where Yukko sends you an urgent message. Go to the point indicated on your map. When you do, Nanami will show up. The only real option is "What I really want is you." Just continue as is until she confesses in the voiceacted cutscene. If this is the second girl that has confessed to you, the achievement "Ladies, Please" as well. As with Sana or the other girls if you've done them first, there is no punishment for dating multiple girls inflicted by the game other than some guilty flavor text from Tak. Whether you accept or decline her confession I'll leave to you.

In order to date Tsukino, you have to complete a series of side-cases.

• Perverted Trio: Professor Panty
  
• Perverted Trio: Ass Catchem
  
• Perverted Trio: Judge Creep n' Peep
  
• The Pervert King

The cases are all presented by her twin brother Yosuke who you can befriend as part of a Friend Mission. The earliest you can do her series of dates is during Chapter 8 if you've been completing side-cases as they've become unlocked. The only prerequisites of these cases are that the first is unlocked through progression through the main story and the other three require the previous ones to be completed first. "The Pervert King" is the capstone of this series of side-cases that involve the Saotome twins. As mentioned before in the Introduction, there are 2 stray cats during this chain and it is sort of appropriate due to her and her brother having profile pictures in the messaging app that are illustrated cats.

The chain of dates is started by Yosuke who texts you asking you to cheer up Tsukino as she has been feeling down lately. And so, proceed with texting her. For gifts she likes simple things. The 50k yen watch will suffice.

Upon getting her to agree to meet up with you, choose an activity and after, you'll sit down in the M-Side cafe to talk.

Pretend you forgot
What are your hobbies?
What kind of men do you like?
(Don't ask about the kind of underwear she likes)

Reassure her strongly

Pledge your loyalty to Tsukino

Why not see if you can get the job first?

Take a picture as well. The date will end and she will text you some more, asking for help for a mock interview. Accept and meet up.

Tsukino will appear in a new outfit and you will be put into Investigation Mode. You need to look at her attire and see what she needs to fix.

The first of the two missable cats is during the request to inspect Tsukino's interview attire for things to fix. Turn around to your right and the cat will be right next to the inflatable beer pint.

For the things you need to spot:

• Examine the button on her suit and tell her that it's wrong
  
• Examine her bag

After you have done this, go to your preferred date activity, and after you're done, you will sit down again to talk.

I’d love to check those out.

Why did you apply here?

• Were you quiet as a child?
  
• Did you apply anywhere else?

How would you describe yourself?
How can you contribute to our company?
Offer a helping suggestion

I’m sure he wouldn't mind marrying you.
Sounds like the opposite of me.
I’m honestly a little jealous.

After this the aforementioned fiance will arrive. It doesn't matter what you choose as an answer for him as it plays out the same way. After he leaves, the date ends. Though, you will need to answer two texts from her as: "You really had it together" and "That’s common". After these messages, you'll be able to ask her out again.

Before you go into this date, even if you set it up, make sure that you have 50,000 yen as you will need it for an unavoidable activity. It may also be advised to get your hands on the poker cheat item - Joker Card; obtainable from the Voluptuous Woman after you become friends - as well if you're not the greatest at poker. When you do ask her out and meet up, you be put into Investigation Mode again to find the difference.

The second of the two missable cats is during the request to inspect the difference on Tsukino. Turn around and the cat will be hiding next to a light pole behind one of the arches of the beer garden's right side.

The difference is her earring on her right ear (your left) and she has never worn this before. Point this out. After you exit Investigation Mode before you can even choose a date activity, you will be stopped by her fiance and forced into a game of poker. No, you can't refuse or weasel out. While the text says one round, technically you can play as many rounds as you have chips and win even after you lose multiple hands; just don't quit if you care about winning against him. No matter the results of the date, Tsukino will still choose to go out with you somewhere else. You will sit down at the Cafe to talk some more.

Say they’re incredible
You should make this your career
I can empathize

Maybe it just wasn't for you?

Empathize with her
That’s tough

Take a selfie and end the date. After this, she will message you again. Just answer enthusiastically and when you get the option to ask her out again, do so.

Before you do this date, it is highly advised, but not required, to get the Miracle Darts from Quickstarter as it makes the forced activity much easier. Meeting up with Tsukino, you will be forced once again into an activity. And as the previous sentence stated, it's going to be darts. Trounce him (or fail) and he'll get so bent out of shape that he challenges you to a "duel." You'll go out back, beat him up in your preferred style and with whatever EX actions you got. After the fight, there will be a few more scenes before he agrees to leave her alone and you'll be able to sit down and talk once more.

That picture changed his life

What kind of designer do you see yourself as?
What can you contribute to our company?
You communicated very well.
Of course

Take a selfie and finish the date. After this, she will message you some more. Pick the more positive of the choices, though, it doesn't matter at this stage as it's pretty much locked in, now. She will text you asking to meet up again, accept.

Her confession is simple. Just do all of the on-screen options until "You mentioned something important..." unlocks. Proceed to hear her confession and choose to accept or deny it.

In order to date Amane, you have to complete this series of side-cases found in the overworld (not from Tender, Yagami's office, or Genda Law).

• The Black Calamity
  
• The Black and White Calamity
  
• The Fire Calamity

These three missions will net you around 30k yen each and consist of a tailing mission and then usually having to intervene with the subject Amane's asking you to protect from a "calamity." They are usually pretty short, clocking in at maybe 10 minutes tops. The earliest you can date Amane is Chapter 10 when she texts you for the first time after completing "The Fire Calamity" which becomes available in Chapter 9 if you've completed the other two.

For gifts, over at Le Marche, choose gifts that have a "mature" description to them as she doesn't usually like gifts otherwise. As for activities, she likes Shogi. If you're like me and either don't like the game or the game's AI is just too brutal on top of the rules being confusing, you may elect to ignore this favorite activity of hers and do another and increase her affection via text, gifts, and the conversation topics on each date.

After getting her to agree to meet up, go do your activity and and after talk.

So you’re volunteering, then?

I’m very interested in you.

You have a very noble attitude.
I’m only kind to you.

After Amane tries to show you how she warns people of their calamities, select the choice, "Be Indirect."

After this, select the option to take a selfie with her. And you will be asked to look over a student from her prophecy of calamity, accept it. The date proceeds to end, though, you will have some wrap-up texts.

After getting texted again, you may invite her out again. Meet up with her and you will go to Beef Zone, you may choose to introduce Amane as your girlfriend, should you desire to. At this point, you'll sit down and talk.

Must’ve have been hard to deal with
I want to help people too

Try to get her full name

Ask her age

• You’re in your twenties, right?
  
• 27

Ask about her love life

• Do you have a boyfriend?
  
• Be a gentleman

Try to get her measurements

• Be modest

After this conversation, Sakakiba of the Keihin Gang (the larger guy), will come in demanding free food. You are given a choice to step in or not, up to you, but you should step in to help Mr. Kim. Bear in mind this fight is like his normal fights you encounter him in when the threat rate is 100%, HOWEVER, he will only have one health bar instead of multiple, BUT he can still enter EX mode and cause Fatal Wound damage if you fail to dodge it. After defeating him, the date will then be complete.

As with before, after date 2, you will get some texts. The answers you should be choosing for these are: "Me too" and "The “sign of the blades” guy?" After this, she will request to meet up again. This time, she will appear in a different outfit. Tell her that she looks nice/beautiful and choose an activity of your choice. After the activity, you will sit down for the talking portion of the date.

Very fun

Express your concern

Could he be a businessman?
Guess the type of his job
Guess the first letter of his job
Give the answer
Yakuza Patriarch

Take a selfie with her and end the conversation, before the date ends, there will be a new prompt to
assume that "the "something getting bigger" is your calamity. She will then be called and the date will end.

She will then text you to finish up officially and you should choose the choices: "I’m worried about your safety." and "I’m single (regardless if you're already dating other girls or not, again, this game doesn't care if you are or not)."

Once able to ask her out on a date again, a "special" interaction is that if you go to La Marche and pick up the Trinity Circle Earrings and give them to her, she will put them on immediately. Kind of a neat thing. Proceed with your preferred activity and after you will sit down again.

I want to keep seeing you

Tell her it’s because she’s charming

There aren't any choices for this.

After you've selected all options, take a selfie and the date will end. She will be called by her patron and will be picked up. She will send you some followup messages and asks you to meet you in your office.

Upon arriving at your office and interacting with the prompt, you will not find Amane there but her patrons (Yakuza). After getting beat a bit, she will arrive and you will have the option to reply "But you just didn’t want to admit it?" She will leave.

Like with Nanami, you will need to keep bugging her via text until she replies. It may take a couple of minutes between prompt attempts. But after she does finally reply, she will agree to meet up with you. NOTE: You will not be able to do any gifts or activities beforehand on this. You will just sit down and talk.

I’ll find a way around it

Thank the cow

No way

While walking back to the meetup spot, she will proceed to confess her love to you. If you have completed the girls' date side stories in the order that I have performed them as well, the achievement will pop for "Now you're just bragging" before you give your choice of answer to accept or reject her confession.

It would be unethical if I didn't credit the content which didn't wholly originate from me.

Cover image by @senukin69[x.com] from their series "Brainrot Girlfriend."
Cat location screenshots from the Neoseeker guide: https://www.neoseeker.com/judgment-sega/walkthrough/Stray_Cat_Locations#Date_with_Tsukino.
Girl section header pictures from the Neoseeker guide: https://www.neoseeker.com/judgment-sega/walkthrough/Girlfriends.
Achievement images from PSN Profiles: https://psnprofiles.com/guide/13909-judgment-trophy-guide.
Responses double checked against various outside written guides including PowerPyx[www.powerpyx.com], Neoseeker[www.neoseeker.com], and GameFAQs[gamefaqs.gamespot.com].