- It's entirely possible to get Amanda's bad ending if you push her too hard and smother her too much. If you happened to get this on top of your date's bad ending, the game ends with the player character cleaning up after the party guests alone beneath the tree in the yard, repeating what their deceased spouse said to them all those years ago: it's going to be okay.
- Getting a bad ending with any of the Dream Daddies, especially when it you recieve it unintentionally. Joseph's good ending counts for many people too.
- When you realise that by completing one Dream Daddy's route, regardless of the ending you get, you fail to help out the other dads with their individual problems. Robert may never reconnect with his daughter, Craig is still pushing himself and not acknowledging his anxiety, Mat may never perform live shows again, etc. It's a bit dramatic to think, but knowing that you were the catalyst to them solving their issues, it does leave you wondering whether they'll ever get their 'good endings' without you.
- The fact that in some routes, you can DIE in front of Amanda. Brian's route especially as the Dadsona's last thoughts are of her.
- Early on in the game, Amanda goes out with her friends to hang out and promises you that she'll call and be home by curfew. When she doesn't, Dadsona is noticeably worried for her safety and gets mad at her for coming home late. If you choose to tell Amanda 'I was scared...', it's implied that this scare hit a little too close to home for Dadsona, as it reminded him of the day Alex died.
- Just as bad is Amanda's reaction to this: the other two dialogue options cause her to get angry and defensive, but if you choose this option, she immediately becomes contrite, almost at a loss for words. It makes her guilty apology the next morning all the more heartbreaking.
- The third date with Robert starts sad and gets sadder as you see what a wreck he's made of himself and how hopeless he feels. You can prompt him onto the path for a better life, and in his Good Ending he's visibly improving, but there's no guarantee he won't backslide.
Tear Jerker / Dream Daddy