There's been various ways that the Wolverine x Jean Grey shipping gets to work. The X-Men cartoons under Haim Saban's production didn't explain much of what happened -- considering that stuff like Angel losing his wings in a very violent fashion, Callisto's deep lust for Angel or stuff like that are considerably cut out for obvious reasons. Wolverine felt like that he was just in love with Jean Grey for the sake of it. But the comics did have a rather bloody backstory which either could have been (1) toned down in Saban's X-Men cartoon or (2) something that couldn't get past the censors.
Yes, Wolverine actually had a crush in the past who looked similar to Jean Grey named Rose O' Hara. No, Jean Grey is NOT a descendant of said person either. What happened was that he had feelings for Rose while she had feelings for someone. His crush on Jean Grey and letting her go is somewhat a psychological need -- he wanted to let Rose to be happy and marry Smitty. However, Rose ended up accidentally killed by him. Later, he would end up killing Jean Grey at her request in both the comics and the movies.
So the truth is it feels like he lets Jean go because he feels like she's just a psychological need than anything else. It's not like his later on/off relationship with Storm (and well the whole wedding with Black Panther felt too random) where it seems he actually does have a thing for her. At this point, I kinda think that he made the right decision of letting his beloved be happy
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