Hello, It took me a while to find contact with you, KnottyGames. I posted comments in Steam about the HeartBreaker achievement. I have read the guide on Steam and your answer that you have to take the path of Katy, Madison and Caroline but there is a problem. On day 1, there are two choices for the route between Katy or Madison. If I take Katy, Madison Road is closed for week 2. If I take Madison, Katy Road is closed. It is not possible to have all 3 in week 2
Not sure how to do spoiler formatting here, so I'll link to the Steam forums that describe the choices there.
https://steamcommunity.com/app/1288920/discussions/0/3370405364914823761/