Judgment - Dating Guide

There are 4 girls you can date in Judgment. All of them are unlocked after finishing related side missions. You need to go on 5 dates with each girl (Amane has 6, she is the only one) and raise their level to 5. After that trophy will pop. 
Also, you can buy a gift for each girl before each date and give it to her, but if you answer all correctly there is no need to spend money.

You will unlock:

Going Steady Trophy - A girl revealed her true feelings. 
Ladies, Please Trophy  - Two girls revealed their true feelings.
Now You're Just Bragging Trophy - Four girls revealed their true feeling

Girls and when:

Sana Mihama - Finish Amidst a Dream Side Mission (Chapter 3)
Nanami Matsuoka - Finish Smart Watching Side Mission (Chapter 7)
Tsukino Saotome - Finish  The Pervert King (Chapter 8)
Amane - Finish The Fire Calamity (Chapter 9)

All girls will contact you via SMS in your menu app some while after completing related side mission. Your goal is to answer the best so you can raise girls level bar. To get an sms, simply run around town and you will get it. I will list all answers bellow so you can follow and use.

Sana Mihama

SMS: "I’ll cheer you up anytime".
Visit her in Theater Square and say respond with "Of course".
SMS: "I expected nothing less of you."
SMS: "I wanted to see you too."

First Date:

Mini-game: "Arcade" (get her a plushy she tells you she wants)
Topic: "Talk about Sana’s Ideal Man"
Answers: "Younger", "15 Years"
Topic: "Talk about Life in Kamurocho"
Answers: "Gently express concern"
Topic: "Talk about Hobbies"
Answers: "I’m actually pretty big on curry.", "Playing pinball."
Take a picture.

SMS: "I did too.", "I’ll be there next time for sure."
Visit her in Theater Square
SMS: "Amazing!", "Then let’s meet up to celebrate."

Second Date:

Pick a location and answer with "Wanna chat in my office?", then with "Sing her praises"
Topic: "Have you written anything new lately?"
Topic: "What made you want to get in to music?"
Answers: "You must have some real talent."
Topic: "Are you dating anyone right now?"
Answers: "That’s a relief.", "Still single."
Take a Picture.
Tell her it's getting late.

SMS: "Make me some more next time.", "We must have looked like a good couple."
Agree to her next text to meet up for another date.

Third Date:

Get your suit on (if you have one, from visiting Le Marche and filling the friend bar there). Choose any location you like.
Topic: "Her Disguise"
Answers: "I like them both."
Topic: "How She’s Been"
Answers: "That is a problem indeed"
Topic: "Who She Likes"
Answers: "Pretend you know who it is"
Take a Picture.

SMS: "Wish it would last forever.", "Thinking about you.", "I guess great minds think alike."
Agree to her next text to meet up for another date.

Fourth Date:

Choose any location you like.
Topic: "Let’s just talk."
Answers: "I still want to see you"
Topic: "Let’s talk music."
Topic: "Let’s talk relationships."
Answers: "I see you as someone special."
Asnwer with "Follow your heart." and "What about that song you wrote?"
Beat the guy outside.

SMS: "I’m totally fine.", "I’d like to hear that sometime.", "Here’s hoping everything goes smoothly."
Agree to her next text to meet up for another date.

Fifth Date:

Meet her in your office.
Select "How’s your latest single?", "How’s that manager of yours?". Accept or reject relationship (no issues choosing any)

Nanami Matsuoka

SMS: "I’m just glad you’re safe."
SMS: "Okay. Well, don’t push yourself."
SMS (send her the text): "Hope you’re doing well.", "Work", "I’m pretty quick like that."
SMS: "Then let’s go out on a date.", "Yeah", "Can’t wait to see you."

First Date:

Meet her and go to Drone Race. After the race select to drink (why not hehe).
Topic: "Tell me a little about yourself."
Topic: "What do you do for work?"
Answers: "I bet that keeps you pretty busy.", "So you’re a workaholic, then?"
Topic: "What are your hobbies?"
Answers: "Actually, same here.", "Yeah, I do."
Topic: "How old are you?"
Answers: "You look young for your age."
Topic: "I’m glad that stalker of yours is gone.", "What’s your philosophy on love?"
Answers: "I still think romance has its place.", "Well said."
Take a Picture.

SMS: "I don’t mind.", "Let’s hang out again."
SMS (text her): "How’ve you been?", "Ask her out", "Do it anyway.", "Of course.", "Ask her out.", "Uh, sure.", "I’m free right now."

Second Date:

Take the girls to Darts (they will take you without you can choose).
Topic: "Ask about preferences in men."
Answers: "Respect can’t be handed out to just anyone.", "Do you not like the concept of dating?"
Topic: "Ask about Yukko"
Answers: "It was when I first saw Nanami-san."
Topic: "Ask about Nanami"
Answers: "I’m very interested."
Topic: "End the conversation"

SMS (Nanami): "Let’s hang out, you and me."
SMS (Yukko): Just text her till the end.
SMS (Text Nanami): "Do it.", "I figured as much", "Wanna hang out somewhere?"
SMS (Nanami): "Busy as usual?"
Try sending text to Nanami, then text Yukko
SMS (text Yukko): "Ask Yukko-san", "I am."
Find Yukko in Wette Kitchen
Answer with "Yeah, I promise.", "I think I can confidently say I like her.", "Let’s do this!"
SMS (Text Nanami): "Ask her to help"
After call with Yukko, text Nanami (if not appearing, run around town a bit). Meet Nanami north of Dragon’s Palace.

Third Date:

Tail Yukko. When prompted, answer with “Hold her close” in middle of tailing. You’ll end up in M Side Cafe.
Topic: "Talk about the investigation"
Answers: "I wonder."
Topic: "Talk about us."
Answers: "Take a step back and apologize.", "But can you see me as a love interest?"
Topic: "Ask her perspective on dating"
Answers: "I’m sorry you had that experience.", "Is that why you haven’t had a boyfriend for a while?"
Take a picture
When Yukko turns answer with "Will you feed me something?".
After the date answer with "I’d rather investigate some things we can do together."

SMS (Nanami): "Yeah, I did."
Yukko will message you.
SMS (text Nanami): You will be asked for dinner, accept.

Fourth Date:

Meet Nanami and repond with "I think you look fabulous". Take here wherever you like. After the mini-game respond with "Why don’t we sit down and talk?"
Topic: "Let’s see who can drink the most."
Answers: "Tell her companionship is important.", "You have someone you like right now.", "You’re actually not that good at cooking.", "I wouldn’t mind eating something you made.", "You haven’t had boyfriend in over five years.", "You like older men.", "I guess I have a chance too.", "You like to do it by yourself.", "You’ve done a job you’d rather not tell anyone.", "You make over five million a year.", "Try to compliment her."
Topic: "Could you ever see me as a boyfriend?"
Take a picture.
Select to go to another bar. Select to tell her the truth.

SMS Nanami, SMS Yukko, SMS Nanami, SMS Yukko, SMS Nanami for the last time and accept new date.

Fifth Date:

Get to marked location, read text and run to Nanami. Respond with "What I really want is you."
Then make her your girl (I had all 4 of them as my girls lol)

Tsukino Saotome

SMS: "I head you were feeling a little down."
SMS: "Maybe I could cheer you up somehow?"

First Date:

Batting Center.
Then make her your girl (I had all 4 of them as my girls lol)
Topic: "Ask about her personal life"
Answers: "Pretend you forgot", "What are your hobbies?", "What kind of men do you like?"
Topic: "Talk about the Twisted Trio"
Answer: "Reassure her strongly"
Topic: "Ask her why she’s so anxious"
Answer: "Pledge your loyalty to Tsukino"
Topic: "Press further about her situation"
Answer: "Why no see if you can get the job first?"
Take a picture.
Agree to help her with interviews.

SMS (Tsukino): "Let’s hang out after our practice interview."
SMS (Yosuke): "What do you mean?", "That’s not true.", "I understand."
Agree to meet with Tsukino when she sends SMS to you.

Second Date:

[MISSABLE] - Do not forget to examine Cat on the right next to yellow stand.
After that examine buttons and tell her to fasten them both, then examine the bag. Take her where you like.

Topic: "Begin the practice interview"
Topic: "Why did you apply here?"
Answers: "Were you quiet as a child?", "Did you apply anywhere else?"
Topic: "How would you describe yourself?"
Topic: "How can you contribute to our company?"
Answer: "Offer a helping suggestion"
Topic: "Ask about her drawings"
Answer: "I’d love to check those out."
Topic: "Ask about her fiance"
Answer: "I’m sure it’s hard on him, too.", "Sounds like the opposite of me.", "I’m honestly a little jealous."
Take a picture.
When her fiance shows up tell that you are her boyfriend (to cook the things up)

SMS (Tsukino): "You really had it together.", "That’s common.", "Ask her out."

Third Date:

[MISSABLE] - Do not forget to examine Cat before the girl.
After that examine her earrings. Keep playing poker until you win one hand, then quit.

Topic: "Talk about her interview"
Answers: "I’m sure you’ll do better next time."
Topic: "Talk about her artwork"
Answer: "Say they’re incredible", "You should make this your career", "I can empathize"
Topic: "Talk about Ryuzenji"
Answer: "Empathize with her", "That’s tough"
Take a picture.

SMS (Tsukino): "That’s very bold of you.", "Being bored."
Recieve SMS from Yosuke and read it.
SMS (Tsukino): "That’s amazing!", "Ask if she’d like to practice"

Forth Date:

Accept Dart challenge and beat the guy.

Topic: "Wrap things up with Ryuzenji"
Answers: "Guess it woke him up to the world of love"
Topic: "Get her psyched
Answer: "What kind of designer do you see yourself as?", "What can you contribute to our company?", "You communicated very well."
Answer: "Of course"
Take a picture.

SMS (Tsukino): "And how’d it go?", "Don’t dwell too much on it. You’ll be fine.", "Sure."

Fifth Date:

Meet her in your office.
Select "Congratulations on the job.", "Press further about her situation", "You mentioned something important…"
Aaaand select to date her or not.

Amane

SMS: "I believed you from the start", "You’re right."
SMS (a bit later saying something about cow), just agree with her and agree to meet.

First Date:

Take her to Shogi and beat her. If you invested in Quickstarted, and payed full summ for Shogi app, you can cheat in shogi using triangle button and selecting that as option.

Topic: "Ask About the Calamities"
Answers: "So you’re volunteering, then?"
Topic: "Find Out More About Her"
Answer: "I’m very interested in you."
Topic: "Ask what’s been bothering her"
Answer: "Be Indirect"
Topic: "Have you had any issues with your job?"
Answer: "You have a very noble attitude.", "I’m only kind to you."
Take a picture.
Accept to watch the student. Answer with "Well, we are partners"

SMS: "Let’s go on a date again.", "That was all you, Amane-san."
She will date you again asking you to a date

Second Date:

Take her to some mini-game. Answer with "She’s my girlfriend."

Topic: "Find out more about Amane"
Topic: "Try to get her full name"
Topic: "Follow up on her profession"
Answers: "Must’ve have been hard to deal with", "I want to help people too"
Topic: "Ask about her love life"
Answer: "Do you have a boyfriend?", "Be a gentleman"
Topic: "Ask her age"
Answer: "You’re in your twenties, right?", "27"
Topic: "Try to get her measurements"
Answer: "Be modest"
Take a picture.
Accept and beat thug.

SMS: "Me too.", "The sign of the blades guy?"
She will date you again asking you to a date.

Third Date:

Compliment her. Take her to some mini-game and win.

Topic: "Ask about the guy"
Answers: "Express your jealousy"
Topic: "Mention how it feels like a date"
Answer: "Very fun"
Topic: "Investigate her new patron"
Answer: "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 picture.
Asnwer with what you like hehe.

SMS: "I’m worried about your safety.", "I’m single"
She will date you again asking you to a date.

Forth Date:

Take her to some mini-game and win.

Topic: "Talk about her patron"
Answers: "Tell her it’s because she’s charming"
Topic: "Talk about the future"
Answer: "I want to keep seeing you"
Topic: "Talk about calamities" twice
Take a picture.

SMS: "I agree"

Fifth  Date:

Meet her in the office and accept the offer.
Answer with "But you just didn’t want to admit it?"

SMS (text Amani): Send empty message, then "How’ve you been?"
SMS (text Amani): Send empty message
Wait a bit, then SMS (text Amani): Send empty message, "Is everything okay?"
Wait a bit, then SMS (text Amani): Send empty message, "I noticed you haven’t said anything"

Finaly she will meet you in the old meeting spot.

Sixth Date:

Topic: "Talk about Ushimata"
Answer: "Thank the cow"
Topic: "Talk about her lost powers"
Answer: "I’ll find a way around it"
Topic: "Talk about seeing each other"

Select whatever you prefer and that is it, dating is done.