Romantic interactions can take place but only one at a time. If one interaction takes place the sim resets. The sim loses any queued interaction. Other interactions, such as friendly can be used and queued without reset. It is only the romantic one, to clarify the interaction after (romantic) resets the sim regardless of what is or isn't queued.
Furthermore, this prevents the follow up of Woohoo, once the interaction (romantic request of woohoo) takes place they reset, therefore no woohoo takes place.
A side note within the save file, the files are not saving. I have followed instruction to remove the save file and find the corrupt one, however this has also continued to be an issue.