Five Dates

Note: there are probably better options to unlock this, but these are all the dialogue choices I made to unlock the achievement.

Make sure to set your career as Healthcare, and include Charity among your interests.

First Date
-Understanding
-Rents
-Have dated older
-We grew apart
-Who's the baby in the profile?
-Gin

Second Date
-Let's do it
-Halloween
-Conservative
-Spiders
-Chocolate
-Cowgirl
-Day (Note: the Sore Loser achievement will unlock here)
-Someday

Third Date
-Consequences
-Second
-The prime minister
-Celebrate the end of lockdown
-Nothing
-I love you
-This will never be the same
-Intelligence
-Principles
-Humour
-Yes
-Yes

Achievement unlocks after the credits, which you can skip with RB.