The two girls, that Leah's brother hooks up with thanks to MC's help, are NOT the targets you can pursue, there's no path to get with them, even for a one night stand.
And the Broken Watch ending seems more like a: "what would happen if...", at least to me it seems that way. Especially since I couldn't access it anymore, after installing the wt mod, so I treat that one as an alternate reality in this game. It exists besides two main paths (boyfriend/badass), so you don't really need to worry about it. And if You were pursuing the badass path, than I'm sure You're aware, that MC gets more selfish with his usage of the watch (I can finally get Ashley's mother into my harem, without worrying about revenge).