I'm attempting to play a Heartbreaker Sim for the first time.
I just had my first breakup (and could they make that music any sadder?), and Constance Shelley was brokenhearted. I noticed I had a bunch of new options in the Friendly category, such as "comfort" and "console." I like Constance and would like my Sim to still be on reasonably good terms with her, so I lined up all of those--and by the time he'd done them all, she had a red heart under her name again! So I had to "ask to just be friends" again, which went over about like you'd expect.
I've only got the one Sim, and he's a Private Investigator whom I watch at all times, because I'm also trying to see if I can get the LTW accomplished without him getting a cheater reputation by flirting with random Sims while in a relationship, which I've read can happen if you send flirty Sims off to a rabbithole job where you can't supervise them. So I know he didn't sneak any Romantic category options in there, because I saw the whole thing.
Basically, my question is if some of the conversation options are miscategorized. I'd like to not suddenly find myself back in a relationship I've just gotten out of!