Yes, the wish to ask to go steady remain after it has been granted and sim is going steady with the sim in question. Later they want to break up or get merried.
If the wish is not granted they want to talk to or flirt to someone they know and are not friends with or a friend and get first kiss and ask to go steady. etc.
Ingame experience right now. Sim asked Tina Tinker to go steady and she accepted. They both fall in love and get flirty in each other's precense. The next day my sim wants to break up, claiming they have not feelings for Tina anymore. They meet up and they are both flirty, cause of each other.
This is what's been happening to me, (svend1928's previous post) on PC though not Xbox like the OG poster. The whim doesn’t complete and then their partner says they've fallen out of love.
I've broken them apart, got them back together, tried again switching who asked who out and still the whim doesn't disappear or award points. One sim has the Soulmate aspiration, and they are behind on fulfillment points, compared to their partner, partly for this reason. (The other has the master spellcaster aspiration. Both of them are spellcasters.)
I hadn't played for a while and came back to this being an issue so I'd imagine it started happening around the time the high school years update came out as OG guesses. That pack came out while I wasn't playing.
