>>149372774
I think that Ult or 2017 cartoon whichever had MJ like that, that Spider-Man Power Pack issue, and Gwen in the OG Ultimate Spider-Man are the closest to what you described even though Peter never really got close to Gwen in that series. Also we discussed in this thread Reign 2 and Insomniac Spider-Man 2 already.
So far only the Power Pack issue has been the only worthwhile use of this concept and luckily it was just a fun series that didn't try too much.