The set-up to How Do I Love Thee? Is a bit disjointed, but once you get into the meat of the story, it's pretty funny. In the beginning, Rick Lenz (the guy who looks like James Stewart) gets a phone call from his mother, Maureen O'Hara. His father is dying and Rick is conflicted about visiting him since they haven't spoken in years. But why? Through flashbacks, we see Rick's relationship with his father, Jackie Gleason, since childhood.
Interspersed into family comedy and an overshadowing cloud of mortality, there's a huge battle between Maureen and Jackie about religion. Obviously, she's a Catholic and he has no faith. The movie sort of feels like it doesn't know what type of comedy it wants to be at times, but you can stick with it for the very touching end result.
For me, the funniest parts of the movie were the scenes involving Shelley Winters. If you read her memoirs, you learned she had a sense of humor about her weight gain, so you can feel free to laugh alongside her. She plays an arty photographer whom Jackie Gleason is constantly trying to seduce - if only she'd give up a little of her romantic demands. In one scene, she wants to literally be swept away, and he picks her up. But while staggering to the bedroom, he drops her! In another, he wants a quick rendezvous, but she asks for time and sweet nothings. Love should bloom like a flower, she says. His reply: "If it's going to flower, it'd better flower fast. I'm a married man with a kid outside and my truck is double parked." I love it!
It's a bit of an oddball, but life isn't always straightforward either. A boy's relationship with his father can be complex with a bunch of different "vignettes" interspersed in memories. This movie will definitely make you laugh, and it might make you cry. Give it a shot, if only for Shelley's sake.