Well let's be honest here, Chris apparently stopped being a "ladies man" in 1998 because throughout the entire series he has never shown any interest in dating or marriage and seems focused on his career. I'm actually more baffled as to what happened between Jill and Carlos because that relationship seemed far more promising. Jill probably would be dating Forrest Speyer if he didn't get pecked to death by crows (I read an old article a long long time ago that Chris and Forrest were good friends and Chris introduced Jill to Wesker and Forrest and they seemed to hit it off good) but the series is so incredibly weak on character development and personal relationships* so I guess we are stuck with silly memes for eternity.
*With the exception of perhaps RE2, Leon + Ada and Claire + Sherry was actually very well done and with RE3 Jill + Carlos showed promise but unfortunately these are the exceptions to the norm and they didn't progress throughout the series as well as they should have. Also 'Shadows of Rose' I think did a decent job with Ethan + Rose and that is a recent title so perhaps Capcom are finally learning the art of character development, but they need to keep it consistent or these are just whimsical outliers.