Five Dates | Walkthrough & Achievement Guide

Maya, Grace, and Saffron

Choices are timed by default; go to Settings and enable 'Streamer Mode (Pause Choices)' to change this behaviour.

Start a new game and complete your profile.

All Set Up
Complete your profile

• Grab beer.

Hold my Beer
Choose to drink

Choose: Maya → Grace → Saffron.

Digital Casanova
Pick your first date

Click on Join to start the video call.

Maya: First Date

• Spanish
  
• Knowledge
  
• Music
  
• Love it
  
• Electronic
  
• I love festivals
  
• Bit of both
  
• Do you miss home?
  
• Admiration
  
• Laugh it off

Grace: First Date

• No
  
• Sounds good to me!
  
• Advanced
  
• Single for a while
  
• Relationship
  
• What's your story?
  
• Yes
  
• I understand

Saffron: First Date

• Yoga
  
• Vegan
  
• Books
  
• Poem

Planting the Seed
Read a poem

• No (I actually love horror movies but 'No' is the right answer for her...)
  
• Yes
  
• Yes

Save 1: once you get to the 'Send two invitations for a second date' screen, quit the game and backup your save at:

Steam\userdata\YOUR-ID\1353270\remote\StoryData

After backing up the file, boot up the game and click on Resume.
Choose: Maya and Grace.

Maya: Second Date

• Dare
  
• Accept

Booty Call
Twerk time

• Eat something without using your hands
  
• Truth
  
• Feet
  
• What do you think of me?
  
• Another round
  
• Truth
  
• Rob a bank

Smooth Criminal
Rob a bank

Between Maya and Grace's second date

• Yes

Grace: Second Date

• Yes - drink
  
• Elaborate
  
• Punched someone
  
• No - don't drink
  
• Never
  
• Met someone famous
  
• Move on
  
• No - don't drink
  
• Agree
  
• Yes

Save 2: once you get to the 'send one invitation for a third date' screen, quit the game and backup your save at:

Steam\userdata\YOUR-ID\1353270\remote\StoryData

Note: Make sure to not replace 'Save 1'.

Boot up the game and click on Resume.
Choose: Maya.

Maya: Third Date

• Is everything alright?
  
• You sure?
  
• No
  
• Move on
  
• Kiss
  
• Yes
  
• Yes
  
• Understand
  
• I'd like to keep seeing you

Nueva Beginnings
3rd Date with Maya was a Success

Quit the game and restore Save 2.
Resume and choose: Grace.

Grace: Third Date

• With who?
  
• Are you talking to other guys?
  
• You matched my friend.

Interrogation
Interrogate Grace

• Secure
  
• Yes

In Contempt of Duvet
3rd Date with Grace was a Success

Quit the game and restore Save 1.
Resume and choose: Saffron → Grace.

Saffron: Second Date

• Moon
  
• Upright
  
• Engage
  
• 2 of Swords
  
• Upright
  
• 4 of Wands
  
• Upright
  
• Engage
  
• Stay ← this choice is important to unlock the next achievement.

Not Alone
Stay to help Saffron

Grace: Second Date

• Pick any choices or just wait for the timer to run out (chapter will autocomplete if you just wait).

Choose Saffron as your third date.

Saffron: Third Date

• How long have you had them?
  
• Quality time
  
• Yes
  
• Come with you!
  
• I'd like to keep seeing you

Only Thyme Will Tell
3rd Date with Saffron was a Success

Paige and Shaina

Start a new game and complete your profile.

Spam TAB to skip already seen scenes.

Choose: Shaina → Paige → Any other girl.

Shaina: First Date

• Understanding
  
• Owns
  
• Have dated older
  
• I wasn't ready to settle down
  
• Yes
  
• Why healthcare?
  
• I don't drink cocktails

Paige: First Date

• Complement
  
• Pub/bar
  
• I'd pay
  
• Accept
  
• Looking for a relationship
  
• Tour of Vinny's flat
  
• Cheeky
  
• Yes
  
• Self-deprecate

Maya: First Date (pick same choices as first playthrough and spam TAB to skip between scenes).

• Spanish
  
• Knowledge
  
• Music
  
• Love it
  
• Electronic
  
• I love festivals
  
• Bit of both
  
• Do you miss home?
  
• Admiration
  
• Laugh it off

Choose: Shaina and Paige as second dates.

Shaina: Second Date

• Let's do it
  
• Halloween
  
• Conservative
  
• Spiders
  
• Chocolate
  
• Cowgirl
  
• Day

Sore Loser
Defeated Shaina

• Now

Paige: Second Date

• Feet for hands
  
• Silver Tongue
  
• Complete silence
  
• Next
  
• Tomorrow

Save 3: once you get to the 'send one invitation for a third date' screen, quit the game and backup your save at:

Steam\userdata\YOUR-ID\1353270\remote\StoryData

Resume and choose Shaina.

Shaina: Third Date

• Draw off
  
• Intelligence
  
• Success
  
• Confidence
  
• Yes
  
• Yes

Light Sleepers
3rd Date with Shaina was a Success

Quit the game and restore Save 3.
Choose Paige.

Before the date

• Healthy

Paige: Third Date

• Ask about her
  
• No
  
• Few
  
• Agree
  
• What's her name?
  
• What's she like?
  
• Accept
  
• I'd like to keep seeing you

We Go Again
3rd Date with Paige was a Success

Crash and Burn

Start a new game and complete your profile.
Choose: Paige → Saffron → Grace.

Page: First Date

• Influencing isn't a job
  
• Persist

Saffron: First Date

• None
  
• Too lazy
  
• Meat-eater
  
• I eat what I want
  
• No

Grace: First Date

• Yes
  
• I don't share food
  
• It's gross
  
• Recently single
  
• Still talk
  
• Not really
  
• Chill out

Choose any two girls: you'll get declined by both.

Crash and Burn
Failed all 3 first dates, no second date

Credits

This walkthrough is based on this guide. All credit goes to 'Mort777'.

[Scrollzy]

Thank you

[dragonadamant]

Finished up all the achievements thanks to you and Mort777. Appreciated!

[dragonadamant]

Thanks so much. Was looking for the least painful way of getting "Crash and Burn" (it's harder to watch bad endings in an FMV game than in something like a visual novel with totally fictional people) and this got it within fifteen minutes.

[claytonhorning]

Props for the guide, lylat.
https://psnprofiles.com/trophies/11713-five-dates/claytonhorning

[claytonhorning]

Maya, "I'm coming, I'm coming." Well, she's gonna be pretty soon with her flatmate.

[Standin.Trafalgar.D.Waterl[A]w]

Worked great thanks!!

[chanendler_bong]

Thank you for the guide, it is useful and very well and clearly made!

[Tricontinental]

Super helpful guide, thanks!

[malen't]

How do I save the games?

[eXe.Scorp1on]

Thank you!