Five DatesFive Dates

Game Details:  Comedy, 2020

Links:  Moby Games, Steam

Walkthrough Updated:  6/11/2024

Suggested Listening:  Where There's Smoke (Ash 25)

Five Dates is a full motion video romantic comedy that deals with the realities of dating against the backdrop of the coronavirus pandemic. You must help guide Vinny, a millennial living in lockdown as he navigates the world of online dating, through multiple storylines and outcomes. There are 15 Steam Achievements, all documented in the walkthrough below. The series continues with Ten Dates.

Setup

After starting a new game, go through the steps of setting up Vinny's profile All Set Up. The best options to select are:

  • First profile picture
  • Finance
  • Travel, Partying, Food & Drink
  • Capricorn

After the initial video you must select from your 5 matches Digital Casanova. During your video call with Callum choose to grab a beer Hold my Beer.

You will now have a series of up to 3 dates with your selections. The remainder of the walkthrough is structured around the names of the 5 matches, so will not be in the same order as your game. The details provided include a way to fail on each of the first dates, and a way to succeed in each of a series of 3 dates (although many other options will also work). There is an achievement for failing all 3 of your first dates in one game Crash and Burn.

You can choose to go on up to 2 second dates, followed by 1 third date.

Maya

Failure

  • Danish
  • Music
  • Hate it
  • Pop
  • Introvert
  • Do you miss home?
  • Comfort
  • Who's Tom?

First Success

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

Second Success

  • Yes
  • Dare
  • Accept Booty Call
  • Eat something without using your hands
  • Truth
  • Role-play
  • What’s your biggest fear?
  • Another round
  • Truth
  • Rob a bank Smooth Criminal

Third Success

  • Is everything alright?
  • Move on
  • No
  • Are you talking to other guys?
  • No
  • Back to mine
  • Yes
  • Confidence
  • I'd like to keep seeing you Nueva Beginnings

Grace

Failure

  • Yes
  • (if you have food as an interest)
    • I don't share food
    • It's gross
  • (if you don't have food as an interest)
    • Rude...
  • Recently single
  • Still talk
  • What's your story?
  • Prefer not to discuss
  • Chill out

First Success

  • No
  • (if you have food as an interest)
    • Sounds good to me!
    • Advanced
  • (if you don't have food as an interest)
    • Go ahead
  • Single for a while
  • Relationship
  • What's your story?
  • Yes
  • I understand

Second Success

  • Yes - drink
  • Elaborate
  • Had a one-night stand
  • No - don't drink
  • Never
  • Met someone famous
  • Move on
  • No - don't drink
  • Agree
  • Yes

Third Success

  • With who?
  • Are you talking to other guys?
  • You matched my friend Interrogation
  • Secure
  • Yes In Contempt of Duvet

Saffron

Failure

  • Running
  • Cocky
  • Meat-eater
  • I eat what I want
  • No

First Success

  • Yoga
  • Vegan
  • Books
  • Poem Planting the Seed
  • No
  • No
  • Why?
  • Yes

Second Success

  • Moon
  • Upright
  • Engage
  • 2 of Swords
  • Upright
  • Engage
  • 7 of Cups
  • Upright
  • Engage
  • Stay Not Alone

Third Success

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

Shaina

Failure

  • Question
  • Independence
  • Rents
  • Have dated older
  • I wasn't ready to settle down
  • No

First Success

  • Understanding
  • Owns
  • Have dated older
  • I wasn't ready to settle down
  • Yes
  • How do you spend your downtime?
  • Hardcore gamer
  • I don't drink cocktails

Second Success

  • Let's do it
  • Halloween
  • Moderate
  • Spiders
  • Vanilla
  • Cowgirl
  • Day Sore Loser
  • Now

Third Success

  • Draw off
  • Intelligence
  • Principles
  • Humour
  • Yes
  • Yes Light Sleepers

Paige

Failure

  • Influencing isn't a job
  • Persist

First Success

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

Second Success

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

Third Success

  • Healthy
  • Ask about her
  • No
  • None
  • Agree
  • What's her name?
  • What's she like?
  • Accept
  • I'd like to keep seeing you We Go Again