there is this one, but is a short one, the premise is kinda of similar, Childhood friend, mom, sister, some other girl he met all dropped the ball with MC at some point and now he have a hard time trusting anyone
Nyanta to Pomeko ~Imasara Shinjiteiru to Iwarete mo Mouteokureda~
I mean, she did something to make MC not remember his childhood friend when he was doing the revenge thing, so I guess is possible to her to mess with his head in other ways.
Honestly the side couple is kinda of fire, i still remember not liking the girl in the start because she was annoying, now she and her boyfriend are one of the main reasons I read, the dude really say "nah, I'd win", and won.
Boyfriend:"Do you really think anyone wants to date a wolf girl? If anyone does they're a freak."
Sister Ex really gave up on a wolf tomboy gf, what a dumbass.