Pressed up against the baseball plot here, the romantic comedy plotline between Jake and Lynn can be taken as an extension of the main idea. Their relationship failed a few years back. The Indians' relationship with Cleveland (at least the way Mrs. Phelps sees it) also failed... well, more than a few years back. The problem is that we can see the Indians' players improving (maybe not why they're improving (except specifically in the case of Vaughn) but simply that they're improving) on the field, we can see them winning games. Jake's wooing doesn't improve, and he doesn't really win any games with Lynn. Rather, he demands her phone number to leave her alone, he shows up at her place of work when that phone number turns out to be fake, and he follows her home from work only to find himself at a dinner party at her fiancé's
(which goes better than one might expect but basically present Jake as a guy still planning a future that he got shut out of when their relationship ended. Like his knees going bad--and I think this is a subplot in the sequel--he has to accept at some point that they won't get any better, and he should accept that he and Lynn might be over. I mean, she is engaged to someone else, and has boxes packed to move in with the guy when Jake ends up finally at her place.)and then he just kinda lucks out and her fiancé gets written out of the film entirely, Lynn gives into nostalgia and comes to a game and, of course, that means she's all in on getting back together with Jake, cue the sex. Because, romantic comedy wants to paint it easy.
As it is, the romantic comedy side doesn't quite gel with the baseball story, either, because the timing is wrong. Lynn is introduced after the tryouts. Imagine Jake runs into Lynn right after he gets back into town, he's not even on the team yet, so he can't claim he's back, he can't claim anything definitive, and maybe he's mature enough or insecure enough to not be the bold asshole he is in the film. And, maybe don't have her engaged to someone else, because then what are we rooting for if we root for Jake to win her over?
We want some other guy's life to fall apart?
I think we're supposed to think Tom is awful, but he's polite, and he lets the conversation keep going even though he's got to realize, before his dinner party guests do, that Jake is openly talking about having kids with Lynn. He is a speed bump on the way to Lynn, and nothing more. But, imagine:
Jake's problem was that he cheated on Lynn. She says of Tom, "I've never found him in bed with a stewardess." And, of Jake: "You don't take anything seriously. Everything's a joke to you." And later in that same scene--the one in the library--"You'll always be the little boy who wouldn't grow up." (And, he still doesn't by the end of the film. His showing up at Lynn's place is the same bullshit he pulls by showing up at Tom's place. His threatening Dorn is hardly mature.)
Jake is introduced in bed with a woman whose face we don't even see. He's hung over, and passed out the wrong direction in his bed, which visually suggests this was probably a one-night stand. It coulda been worse. He's playing in a Mexican league and there's an extra departure scene in the script:
TAYLOR approaching his MANAGER.
Let's go, Taylor. You're up.
Fine. Leave your uniform.
But I changed at the motel.
Leave your uniform.
TAYLOR coming out of the stadium, his bats and gloves over his shoulder. He has on his spikes and a pair of boxer shorts.Stripped down is not an improvement on his prior scene, waking up with a sombrero on his face.
And he brags about being wanted by stewardesses when Lynn brings it up. His plotline with Lynn should not be about her realizing that moving on was a bad move. He should still be getting women coming up to him in bars like one approaches Vaughn at one point. Then, he has something to give up for Lynn. Instead, he's the old player with the bad knees and a failed relationship and he cannot really fix either of those things. He can just accept them.
Which, unfortunately, is more in line with Major League II's Jake Taylor.
Going for what you want is all well and good as a message, but when what you want has a life of its own, that shit is not up to you and you alone. The push harder approach is not the way to go. And, proclaiming in the locker room that now you should try to win the whole fucking thing is stupid, because what the hell were they trying to do before?