In my first game in Bridgeport, I played a single female pianist, with plans to start a band. On her first day, she went to the theater to take a piano class. Matthew Hamming was there, and she asked for his autograph. He hit on her. So I had her try to impress him. It's been a long time, so I don't remember whether she was able to impress him enough to socialize with him, but it seems she must have. A day or two later, he came to her apartment to visit her. While there, he started flirting with her, and they ended up going outside to watch the stars. By this time they were romantically involved.
A day or two later, he invited her to his house for a party, but she was the only one who came. As I was choosing interactions for her to do with him, I found one asking him to break up with another woman. He was not going steady with anyone on that day that he visited her at her home. A day or two after that, he was at Marina Field as my sim was passing by. I decided to get some revenge on him for two-timing her. Of course, the paparazzi were there taking pictures and notes. I had my sim walk up with him and spam romantic actions with him, including lots of kissing and making out. The plan was to make the other woman angry with him for cheating.
The next time my sim saw him, he was no longer going steady with the other woman. I wanted to know what had happened, so I saved, then switched households to check on his relationship with the other woman, and his moodlets. He was still good friends with the ex-girlfriend, and had no negative moodlets from breaking up. So apparently, he and the other woman just decided they didn't want to be together after all. My sim eventually married Matthew, and they had two children together.