It’s become received wisdom that many movies, often romantic comedies, frequently feature behaviour towards an object of affection from an often male protagonist which is depicted as romantic and charming proof of devotion, but that would in real life count as stalking, and be, if not downright illegal, subject to pretty severe condemnation.
That said, what are some actual examples from movies of stalking or other inappropriately obsessive behaviour that is depicted as romantic? In Wall-E, the titular garbage robot is infatuated with EVE, the female researcher who is aloof to the point of hostility. But when she goes into hibernation mode, he uses the opportunity of having her comatose and unresisting to dress her up and take her on a “date”. Yeah, try that in real life with an unconscious girl some time.
Bed of Roses - Christian Slater becomes obsessed with a woman he’s never met; starts watching her through her window and sending her hundreds of bouquets of flowers from a “secret admirer.”
High Fidelity - A jealous John Cusack stalks his ex-girlfriend and her new man by showing up outside their apartment and making countless phone calls.
Say Anything - A lot of people consider John Cusack’s holding a boombox outside Ione Skye’s house to be romantic as hell, but technically it’s stalking.
That’s a pretty loose definition of stalking. Anyone who goes to someone else’s house once is stalking? He’s not peering in windows, not monitoring her whereabouts, not making unwelcome advances, and not repeating a pattern of harassment. I think the bar needs to be a bit higher before you can call it “technically” stalking.
The hero in Bedazzled (both versions). Uses multiple wishes from The Devil in order to ingratiate himself into his love’s life, rather than just, you know, talking to her.
Aladdin. Uses multiple wishes to pass himself off as a prince so that he can get the girl.
Beauty & The Beast. Kidnaps Belle’s father to force her to live with him.
In Addicted to Love, she stalks her ex, who is dating the ex of Matthew Broderick, who is also stalking the couple. Naturally, the stalkers end up falling in love with each other.
Big Fish. Ewen McGregor’s character, Edward, seems his dream girl, Alison Lohman, at a circus. He works for the ringmaster, and only works for information about her. He eventually determines her name, and where she goes to college. He shows up at her door unannounced, introduces himself, and asks her out. She reveals that she’s engaged. He leaves, but says that he loves her and he will marry her. He shows up outside her window one day, with hundreds of her favorite flowers, saying he called every florist in (I think) 3 counties to get them all.
LA Law: IIRC, Harry Hamlin pesters Susan Dey after she repeatedly turns him down, uses a professional meeting as a pretext to meet and size up her fiancé, and interrupts their wedding in a gorilla suit.
Also IIRC, since it was the mid-80’s, even the gorilla suit had accentuated shoulder pads.
I thought about this as a nominee, but rejected it because the OP stated that the stalkerish behavior should be depicted as romantic. Niether Broderick’s nor Ryan’s character’s stalking of their exes is depicted as romantic … they are both depicted as obsessive losers who were ruining their lives with all the stalking.