Ah sort of like a smoocher lifestyle. I haven't tried that yet, only homeless. But homeless sim gets boring quickly because there is really not a whole lot to do.
I have a little thing with that "inappropriate behaviors" as well. I have a female sim who accidentally got pregnant on a night out with her love interest. Natural she often comes over the guy's house to spend the night so he can take care of her. Even after she asked to stay the night (or to be asked by the guy), she was often scolded for misbehaviors by sleeping the same bed with him. To work around it I had to "Make Active" both sims very often by switching household (Twallan's Master Controller's Make Active makes switching household a lot faster than going through Edit Town).
I suppose BenC0722's suggestion on Inappropriate but in a Good Way reward is a good choice. However, it does require using up precious lifetime happiness point. Or just to remedy the problem, you can cheat to give that sim just enough Lifetime happiness to get that reward, and to think of it as a way to bypass certain TS3's annoyance instead of cheating to gain advantage.
I work for a living, but I don't necessarily live for a working.