# Movies where a nice guy loses his girlfriend to a nicer guy?(spoilers in op) **URL:** \ **Category:** Cafe Society\ **Created:** [January 9, 2006, 6:13pm UTC](https://boards.straightdope.com/t/movies-where-a-nice-guy-loses-his-girlfriend-to-a-nicer-guy-spoilers-in-op/339184 "2006-01-09T18:13:09Z")\ **Posts on this page:** 20\ **Page:** 1
**Author:** ![teemingONE](https://avatars.discourse-cdn.com/v4/letter/t/b4bc9f/32.png) [@teemingONE](https://boards.straightdope.com/u/teemingONE)\ **Post date:** [January 9, 2006, 6:13pm UTC](https://boards.straightdope.com/t/movies-where-a-nice-guy-loses-his-girlfriend-to-a-nicer-guy-spoilers-in-op/339184/1 "2006-01-09T18:13:09Z")
Over the weekend I watched _Wedding Crashers_ and _Big Fish_ and in both movies we see that a nice guy wins the heart of the beautiful girl right before she is about to marry a complete jerk. I find this to be a regular occurrence in many movies. Are there (good/enjoyable/watchable) films where the hero takes the girl from a relatively nice guy? ---
**Author:** ![SSG\_Schwartz](https://avatars.discourse-cdn.com/v4/letter/s/e9a140/32.png) [@SSG\_Schwartz](https://boards.straightdope.com/u/SSG_Schwartz)\ **Post date:** [January 9, 2006, 6:41pm UTC](https://boards.straightdope.com/t/movies-where-a-nice-guy-loses-his-girlfriend-to-a-nicer-guy-spoilers-in-op/339184/2 "2006-01-09T18:41:35Z")
Off the top of my head, how about: 16 candles There’s something about Mary Pretty in Pink (sort of) ---
**Author:** ![Gangster\_Octopus](https://avatars.discourse-cdn.com/v4/letter/g/a8b319/32.png) [@Gangster\_Octopus](https://boards.straightdope.com/u/Gangster_Octopus)\ **Post date:** [January 9, 2006, 6:44pm UTC](https://boards.straightdope.com/t/movies-where-a-nice-guy-loses-his-girlfriend-to-a-nicer-guy-spoilers-in-op/339184/3 "2006-01-09T18:44:02Z")
Reality Bites ---
**Author:** ![Skammer](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/skammer/32/143_2.png) [@Skammer](https://boards.straightdope.com/u/Skammer)\ **Post date:** [January 9, 2006, 6:44pm UTC](https://boards.straightdope.com/t/movies-where-a-nice-guy-loses-his-girlfriend-to-a-nicer-guy-spoilers-in-op/339184/4 "2006-01-09T18:44:38Z")
There was _My Best Friend’s Wedding_, where the heroine (Julia Roberts) decides to steal the fiance of a very nice Cameron Diaz. Kinda what you are asking, except the sexes are reversed. ---
**Author:** ![Annie-Xmas](https://avatars.discourse-cdn.com/v4/letter/a/ecc23a/32.png) [@Annie-Xmas](https://boards.straightdope.com/u/Annie-Xmas)\ **Post date:** [January 9, 2006, 6:57pm UTC](https://boards.straightdope.com/t/movies-where-a-nice-guy-loses-his-girlfriend-to-a-nicer-guy-spoilers-in-op/339184/5 "2006-01-09T18:57:06Z")
The Graduate ---
**Author:** ![Dunderman](https://avatars.discourse-cdn.com/v4/letter/d/ecb155/32.png) [@Dunderman](https://boards.straightdope.com/u/Dunderman)\ **Post date:** [January 9, 2006, 6:59pm UTC](https://boards.straightdope.com/t/movies-where-a-nice-guy-loses-his-girlfriend-to-a-nicer-guy-spoilers-in-op/339184/6 "2006-01-09T18:59:22Z")
> [@Skammer](#): > > There was _My Best Friend’s Wedding_, where the heroine (Julia Roberts) decides to steal the fiance of a very nice Cameron Diaz. Kinda what you are asking, except the sexes are reversed. If sex reversal is allowed, there’s _Sound of Music_. ---
**Author:** ![Raguleader](https://avatars.discourse-cdn.com/v4/letter/r/258eb7/32.png) [@Raguleader](https://boards.straightdope.com/u/Raguleader)\ **Post date:** [January 9, 2006, 7:00pm UTC](https://boards.straightdope.com/t/movies-where-a-nice-guy-loses-his-girlfriend-to-a-nicer-guy-spoilers-in-op/339184/7 "2006-01-09T19:00:57Z")
> [@Skammer](#): > > There was _My Best Friend’s Wedding_, where the heroine (Julia Roberts) decides to steal the fiance of a very nice Cameron Diaz. Kinda what you are asking, except the sexes are reversed. Plot-ending spoiler for My Best Friend’s Wedding: IIRC, she fails to do this at the end. ---
**Author:** ![drm](https://avatars.discourse-cdn.com/v4/letter/d/a88e57/32.png) [@drm](https://boards.straightdope.com/u/drm)\ **Post date:** [January 9, 2006, 7:27pm UTC](https://boards.straightdope.com/t/movies-where-a-nice-guy-loses-his-girlfriend-to-a-nicer-guy-spoilers-in-op/339184/8 "2006-01-09T19:27:44Z")
> [@Sgt. Schwartz](#): > > 16 candles Are we referring to The Geek losing Samantha to Jake Ryan or Jake losing Caroline (how cool is the name Haviland Morris by the way) to The Geek. I’m not sure either of them fit the criteria. The Geek and Sam were really never dating and I haven’t seen it in a while but it seemed he was more than happy to help Jake woo her because he ended up (sort of) with Jake’s girlfriend (and the two of them seemed to break up amicably thus never really ‘losing’ each other). My addition (if sex reversal is allowed) is **Serendipity**. Jonathan was all set to marry Halley Buchanan, who was a really nice (and not to mention hot) girl and Jonathan, through a series of coincidences ends up with Sara Thomas who is also very nice. ---
**Author:** ![Little\_Nemo](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/little_nemo/32/3120_2.png) [@Little\_Nemo](https://boards.straightdope.com/u/Little_Nemo)\ **Post date:** [January 9, 2006, 7:29pm UTC](https://boards.straightdope.com/t/movies-where-a-nice-guy-loses-his-girlfriend-to-a-nicer-guy-spoilers-in-op/339184/9 "2006-01-09T19:29:00Z")
_Not Another Teen Movie_ was a parody of various teen movie cliches. One of the jokes was two characters, who were both in love with the lead actress, arguing about who she would pick in the end. “She’ll pick me. I’m the self-obsessed jock who’s reformed and become a sensitive guy because of her. We’re bound to end up together. Like in _She’s All That_.” “Oh yeah? Well, I’m the best friend who’s always secretly loved her and she’ll realize I’m more than just a friend in the final scene. Like _Some Kind of Wonderful_.” ---
**Author:** ![Infovore](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/infovore/32/420_2.png) [@Infovore](https://boards.straightdope.com/u/Infovore)\ **Post date:** [January 9, 2006, 7:33pm UTC](https://boards.straightdope.com/t/movies-where-a-nice-guy-loses-his-girlfriend-to-a-nicer-guy-spoilers-in-op/339184/10 "2006-01-09T19:33:17Z")
> [@Skammer](#): > > There was _My Best Friend’s Wedding_, where the heroine (Julia Roberts) decides to steal the fiance of a very nice Cameron Diaz. Kinda what you are asking, except the sexes are reversed. Same with _Corpse Bride_, if animated reversal is allowed too. 🙂 ---
**Author:** ![Little\_Nemo](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/little_nemo/32/3120_2.png) [@Little\_Nemo](https://boards.straightdope.com/u/Little_Nemo)\ **Post date:** [January 9, 2006, 7:35pm UTC](https://boards.straightdope.com/t/movies-where-a-nice-guy-loses-his-girlfriend-to-a-nicer-guy-spoilers-in-op/339184/11 "2006-01-09T19:35:45Z")
Let’s not forget classics like _The Philadelhia Story_ - Jimmy Stewart, the epitome of nice guys, loses Katherine Hepburn to Cary Grant. ---
**Author:** ![wolfman](https://avatars.discourse-cdn.com/v4/letter/w/a8b319/32.png) [@wolfman](https://boards.straightdope.com/u/wolfman)\ **Post date:** [January 9, 2006, 7:44pm UTC](https://boards.straightdope.com/t/movies-where-a-nice-guy-loses-his-girlfriend-to-a-nicer-guy-spoilers-in-op/339184/12 "2006-01-09T19:44:55Z")
Liar Liar might fit. A very selfish and somewhat amoral guy(Jim Carrey) gets divorced. And his ex-wife hooks up with a really nice but boring other guy(Cary Elwes). Carrey eventually gets her back when he learns to be a nice, moral guy. ---
**Author:** ![Robot\_Arm](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/robot_arm/32/18280_2.png) [@Robot\_Arm](https://boards.straightdope.com/u/Robot_Arm)\ **Post date:** [January 9, 2006, 7:51pm UTC](https://boards.straightdope.com/t/movies-where-a-nice-guy-loses-his-girlfriend-to-a-nicer-guy-spoilers-in-op/339184/13 "2006-01-09T19:51:44Z")
> [@Little Nemo](#): > > Let’s not forget classics like _The Philadelhia Story_ - Jimmy Stewart, the epitome of nice guys, loses Katherine Hepburn to Cary Grant. Except that Jimmy Stewart wasn’t the nice guy in that movie. The two male leads were cast against type (to great effect), with Cary Grant as the upstanding, boy-scout type, and Jimmy Stewart as the rogue. ---
**Author:** ![Speaker\_for\_the\_Dead](https://avatars.discourse-cdn.com/v4/letter/s/c77e96/32.png) [@Speaker\_for\_the\_Dead](https://boards.straightdope.com/u/Speaker_for_the_Dead)\ **Post date:** [January 9, 2006, 8:13pm UTC](https://boards.straightdope.com/t/movies-where-a-nice-guy-loses-his-girlfriend-to-a-nicer-guy-spoilers-in-op/339184/14 "2006-01-09T20:13:35Z")
> [@Robot Arm](#): > > Except that Jimmy Stewart wasn’t the nice guy in that movie. The two male leads were cast against type (to great effect), with Cary Grant as the upstanding, boy-scout type, and Jimmy Stewart as the rogue. How dare you call Cary Elwes boring looking! He was lovely in _The Princess Bride_. My girlfriend wholeheartedly agrees. 😉 _Sweet Home Alabama_ is a great example of this. Even at the end, the good, urban husband shows how great he is by gladly stepping aside for Reese Witherspoon’s character’s sake. ---
**Author:** ![middleman](https://avatars.discourse-cdn.com/v4/letter/m/e9a140/32.png) [@middleman](https://boards.straightdope.com/u/middleman)\ **Post date:** [January 9, 2006, 8:14pm UTC](https://boards.straightdope.com/t/movies-where-a-nice-guy-loses-his-girlfriend-to-a-nicer-guy-spoilers-in-op/339184/15 "2006-01-09T20:14:32Z")
Reese Witherspoon leaves her nice guy fiancee played by Patrick Dempsey for her “rough around the edges” supposedly ex-husband. ---
**Author:** ![Robot\_Arm](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/robot_arm/32/18280_2.png) [@Robot\_Arm](https://boards.straightdope.com/u/Robot_Arm)\ **Post date:** [January 9, 2006, 8:33pm UTC](https://boards.straightdope.com/t/movies-where-a-nice-guy-loses-his-girlfriend-to-a-nicer-guy-spoilers-in-op/339184/16 "2006-01-09T20:33:09Z")
> [@Speaker for the Dead](#): > > How dare you call Cary Elwes boring looking! Uh, sorry? ---
**Author:** ![JoeSki](https://avatars.discourse-cdn.com/v4/letter/j/b487fb/32.png) [@JoeSki](https://boards.straightdope.com/u/JoeSki)\ **Post date:** [January 9, 2006, 9:11pm UTC](https://boards.straightdope.com/t/movies-where-a-nice-guy-loses-his-girlfriend-to-a-nicer-guy-spoilers-in-op/339184/17 "2006-01-09T21:11:20Z")
In Sleepless in Seattle Meg Ryan falls for Tom Hank’s character, leaving her nice, boring, and weak fiance played by Bill Pullman behind. ---
**Author:** ![Jonathan\_Chance](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/jonathan_chance/32/701_2.png) [@Jonathan\_Chance](https://boards.straightdope.com/u/Jonathan_Chance)\ **Post date:** [January 9, 2006, 9:12pm UTC](https://boards.straightdope.com/t/movies-where-a-nice-guy-loses-his-girlfriend-to-a-nicer-guy-spoilers-in-op/339184/18 "2006-01-09T21:12:29Z")
_An Ideal Husband_ as recently done with Rupert Everett has him winning the heart of Miss Mabel over the apparently very nice Tommy. There’s even a shot of him attending their wedding with a sad and wistful expression. Poor Tommy! But some things are clearly just meant to be. ---
**Author:** ![Skammer](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/skammer/32/143_2.png) [@Skammer](https://boards.straightdope.com/u/Skammer)\ **Post date:** [January 9, 2006, 9:13pm UTC](https://boards.straightdope.com/t/movies-where-a-nice-guy-loses-his-girlfriend-to-a-nicer-guy-spoilers-in-op/339184/19 "2006-01-09T21:13:16Z")
Oh, I forgot - _The Notebook_. Nice, loving, good-looking wealthy businessman loses his fiance to nice, working class artist-type. I felt sorry for him. I had blocked that film from my memory. ---
**Author:** ![JerH](https://avatars.discourse-cdn.com/v4/letter/j/bb73d2/32.png) [@JerH](https://boards.straightdope.com/u/JerH)\ **Post date:** [January 9, 2006, 9:19pm UTC](https://boards.straightdope.com/t/movies-where-a-nice-guy-loses-his-girlfriend-to-a-nicer-guy-spoilers-in-op/339184/20 "2006-01-09T21:19:04Z")
_Serendipity_ - both of the main characters left their perfectly nice fiances. [Next page](https://boards.straightdope.com/t/movies-where-a-nice-guy-loses-his-girlfriend-to-a-nicer-guy-spoilers-in-op/339184.md?page=2)