Five Dates

Make sure your profession is Other and your astrological sign is Sagittarius, the other profile settings don't matter.

Send date invites to Grace, Saffron, and Paige.

For Grace, select these options:
-Yes
-I don't share food
-It's gross
-Recently single
-Still talk
-Not really
-Chill out

For Saffron, select these options:
-None
-Too lazy
-Meat-eater
-I eat what I want
-No

For Paige, select these options:
-Influencing isn't a job
-Persist

You will talk to your friend after failing these three dates, and then will be taken back to the date selection screen. Send invites to Saffron and Paige, whom will both reject you and take you to the credits screen. You can skip the credits by pressing RB, upon which the achievement will unlock at the main menu.