When the Nice Guy Still Finishes Last: An Overanalysis of “Win A Date With Tad Hamilton!”

Yesterday on Twitter I posted, “Someday I hope to live in a world where Win a Date With Tad Hamilton! is recognized as the cinematic masterpiece that it is.”

At the time, I was being more than 50% ironic, but I had no idea that I was about to experience the film on a whole new level.

Win a Date With Tad Hamilton has held a bizarre but fixed place in my heart since I saw it in the cinema in 2004 with college friends. I mostly like it (and bought it) because I associate it with good memories. It’s not my usual type of movie: It’s a romantic comedy, and I’m not a huge fan of any of the actors in it. (I mean, they’re all Americans.) On its surface, the movie is a cinematic pop song: bright, colorful, bubbly, fun, and incredibly shallow.

Why do I like it? Well, the same reason I like a lot of shallow pop songs: It’s fun. I mean, look at the plot, according to IMDB: “A small-town girl wins a date with a male celebrity through a contest. When the date goes better than expected, a love triangle forms between the girl, the male celebrity, and the girl’s best friend.”

As a mad crazy fangirl who loves film and gets way too attached to her favorite performers, what’s not to like???

But when I rewatched the movie last night, something changed, and I recognized WaDwTH as an epic work of profound tragedy.

Not quite Shakespearean tragedy—more like Russian-novel tragedy. But I am convinced that you could do a “gritty reboot” of WaDwTH and explore some of its darker elements. Unfortunately, to explain this, I will need to pick apart some elements of the plot, and spoil the ending. So there it is: Here be spoilers. You have been warned.

Shall we begin?

Rosalee (Kate Bosworth) and Cathy (Ginnifer Goodwin) are two of Tad Hamilton (Josh Duhamel)’s biggest fans, while Pete (Topher Grace), Rosalee’s BFF, suffers through their squees and swoons and ponderations about Tad Hamilton’s real-life persona.

The conversations between the two girls about Tad are actually a cute, spot-on spoof of celebrity obsessions. (Tad Hamilton plays a lot of “classic” romantic hero roles, like a WWII soldier and a cowboy. If the movie were a darker satire of fame and celebrity obsessions, I think he would play more villains and antiheroes.) One of my favorite exchanges comes in the first scene:

Cathy: Rosie, do you think that, in real life, Tad Hamilton is the man he seems to be on the screen?
Rosalee: Absolutely! I mean, you just can’t fake that kind of thing.
Cathy: What do you think Tad Hamilton is doing right now?
Rosalee: I’ll bet he’s in church.
[Cut to a scene of Tad simultaneously speeding, smoking, drinking, and making out with a gorgeous model in his sports car.]

But alas, Tad Hamilton’s real-life debauchery is affecting his job offers, and so his handlers come up with a way to brighten up his image: “Win a Date With Tad Hamilton!” a contest that requires a $100 donation to a save-the-children foundation.

(Cathy: “That is so like him!” Rosalee: “Saving children? I know!”)

(I…have also had that conversation before.)

Cathy and Rosalee, who both work in the same grocery store (under Pete’s management) in West Virginia, get customers to donate enough money for Rosalee to enter the contest—and win. Commence more squees and swoons.

Unfortunately, not everyone is pleased with this turn of events: Pete is not only tired of seeing/hearing about Tad Hamilton, but he’s secretly in love with Rosalie. When he and Cathy see Rosalee off at the airport for her flight to L.A., he is obviously concerned that his best friend is about to become another notch in some other guy’s bedpost.

Tad Hamilton has his appeal, and he develops feelings for Rosalee and attempts to woo her. But in the end, she runs back into the arms of Pete, her best friend who has loved her the whole time.

This used to make me go “aww,” but last night, it broke my heart in a different way.


“What have I done??”


Here is where the most tragic element of the story appears: The ever-controversial “Nice Guy” issue.

Pete is the classic negative version of the Nice Guy archetype, as described so well on (where else?) XKCD and Wikipedia. For the Wikipedia description, click the link, then go to the headline “Heartless Bitches International” and you will see a perfect description of what Pete’s relationship with Rosalee is like.

Pete not only has known Rosalee for years and is familiar with her ways, but as the “nice guy,” he is established early on in the movie as the one who “deserves” her affections more.

But does he? A look at his behavior strongly suggests otherwise. He talks down to Rosalee a lot (admittedly, she is quite naïve bordering on stupid sometimes), he’s snide and dismissive toward her interests, and in fact, the audience never sees him speak a kind word to her. After Rosalee’s awkward but charming date with Tad, the actor is so taken with her that he flies to West Virginia and shows up at her place of work, wanting to get to know her better. When this happens, Pete acts territorial and possessive and eventually tries to sabotage the burgeoning relationship. Pete’s belief that he has any sort of claim on her is uncalled-for at any time and place, but it is particularly heinous that he is so possessive when he has done nothing to establish any kind of exclusivity between him and Rosalee.

One early scene intercuts shots of Pete and Tad in their respective residences: Tad is in his modern Hollywood mansion, making a microwave dinner that he eats alone in front of his high-tech TV. All this, I suppose, is meant to convey the lonely, empty life he leads under all the fame, fortune, and glamor. Pete is in his small-town apartment, making a sandwich, and eventually settles down to read Flannery O’Connor, which I guess is meant to imply that he is deep and intelligent. But the thing is, both these guys are eating alone in their homes at night. OK, Pete has his dog and actually cracks a smile, but the rest of the movie makes it obvious that he would rather be with Rosalee. And if he grew the balls to do anything about it, he would be. But he doesn’t.

Who does? Tad.

Heck, if it were only a matter of loneliness/solitude, Pete wouldn’t even have to work up the nerve to say anything to Rosalee in particular. The local barmaid, Angelica (Kathryn Hahn) has a thing for Pete, and makes that very clear. But until the last 20 minutes of the movie, she is only a comic figure, and Pete is as dismissive of her interest in him as he is dismissive of … everything else. I’m guessing he is intimidated by an independent, personable, unconventionally attractive, no-nonsense woman with a personality (and–gasp–tattoos) because it reminds him of his crippling insecurity and even more crippled masculinity.



But I’m tired of Pete. Let’s take a look at Tad. Rosalee is clearly star-struck and awkward, but Tad is at least polite, and not only because there are paparazzi at the restaurant–he’s nice to her in the limo beforehand, even after she gets motion sickness and throws up. After the date, Tad invites Rosalee back to his place. She already has an inkling of his intentions, and agrees, but when they get to his house, she changes her mind and asks to be taken back to her hotel instead.

What does Tad do? He respects her choice and honors her request. Sorry to get heavier than even I intended, but I have to point out that, at a time when “rape culture” and “no means no” are hot-button social issues, this bit of Tad’s character is hugely important. Although the movie is trying to imply that Tad is an entitled jackhole (and, in many ways, he is) with sleazy intentions, he’s taken aback, says, “Good for you,” and offers to accompany her back to the hotel. No, not to carry out his sleazy intentions there—he never even gets out of the limo once they arrive—but simply to wish her well, and give her a good-bye kiss. Someone who was more a jerk, more entitled, or who was only interested in Rosalee because she poses a “challenge” probably would be…less accommodating.

But even after the evening is over and Rosalee has returned to normal life at the grocery store with Cathy and Pete, Tad has not forgotten her. After arriving in West Virginia and taking her to lunch, he tells her that she has “a goodness” he wants in his life, and asks to get to know her better, away from the L.A. rat race and the celebrity life. At one point, he tries to win her over by quoting a line from one of his movies, but Rosalee recognizes the quote and calls him out on it. He is appropriately humbled.

Rosalee: Is that how you get women?? You steal lines from your own movies?
Tad: Not anymore!
Rosalee: Well I hope not, because that would seriously shoot a hole in your credibility.

Tad insists that his desire to know Rosalee’s “goodness” is just platonic, but 10 hours later, after dinner and a movie, they’re making out in his car, because…well, come on. It’s Tad Hamilton.

But things don’t get too far, because the cops arrive. “Someone,” aka Pete, pulled a Sherlock and deduced what they were up to, and reported a car being illegally parked there after curfew. Rosalee, in classic Dr. Watson style (albeit stupid Watson), recognizes Pete’s intrusion on her date and pitches a fit. The next day, Pete lectures her about her behavior and tries to tell her what a shallow sleaze Tad is. This is especially unfair because it was Rosalee’s idea to “park,” but of course all-knowing Pete knows better what’s good for Rosalee than she does, and he doesn’t stop lecturing her.


"You can't trust him. That's why his pecs are so big: THEY'RE FULL OF SECRETS."

“You can’t trust him. That’s why his pecs are so big: THEY’RE FULL OF SECRETS.”


But even though Pete insists that Tad’s interest isn’t real or lasting, Tad commits to buying a nearby house and farmland (or a “tax shelter,” as Pete derisively calls it) and even Pete has to admit that he might have lost whatever chance he had with Rosalee. Things look dicey for Tad and Rosalee, though, when Tad’s agent and manager show up to tell him he’s gotten an offer from a major director, and it looks like Tad is going to back off from his big talk about wanting to live a simpler, more genuine life. But Rosalee encourages him to take the part, and Tad asks her to come back to California with him, to continue being a good influence. She agrees.

But then, after being encouraged by Angelica (who is awesome and deserves better anyway), Pete goes to Rosalee’s house the night before she leaves and tells her that he loves her. Her response: “Now? You say these things to me NOW? After 22 years of being my friend?” She shoots him down, and Pete leaves.

Yes. You go, girl. Choose the guy who is not only rich and handsome and driven, but who has actually spoken kindly to you, demonstrated respect for your desires and decisions, and made his feelings clear.

But then, disaster truly strikes. On the private plane to California, one wrong word leads to another, and Tad confesses to her that he got a private lecture from Pete that not only included threats of violence if Tad broke her heart, but an overly detailed description of Rosalee’s six different smiles. This is enough to win Rosalee over to the other side, and–in a request reminiscent of the night she and Tad met–she asks if he could turn the plane around and take her home. He complies, with a wry remark that it’s been a big week for him, as he “got bit in the ass for being honorable for the first time.”

“How should I deal with my grief tonight: should I weep into my pile of fangirls, or my pile of money?”

Back home, Rosalee tracks down Pete and falls into his passive-aggressive arms.

The thing is, up until this point, there is never any sign that Rosalee is interested in Pete in any way beyond friendship. Clearly the idea has never crossed her mind. Tad shows his interest, and yeah, maybe it’s “unfair” that he has the money and influence to pull big gestures like flying from LA to West Virginia or buying a house at the drop of a cowboy hat, but Pete had years of opportunity, and squandered it.

Unlike with Tad, there’s not even any indication that affection for Rosalee encourages Pete to be a better person. As I have said before, he is sarcastic and rude and only speaks well of her to other people, never to her face. When he confesses his love at the worst time ever, he acts offended and entitled when she turns him down and strongly implies that maybe he should have done things differently. At the end of the movie, however, Pete is rewarded for his behavior, even though he has not really learned anything.

Tad is the one whose eyes have been opened to a new lifestyle, who at least acts interested in her life and her small town, whose entitled behavior is challenged, and who wants to do the right thing, however ineptly he may go about it. But it is Pete–the passive/passive-aggressive, derisive, possessive, weak, disingenuous character–who gets the girl in the end.

And where does this leave our “heroine,” Rosalee? The final minutes of the film begin with her literally flying high (in a private jet) through sunny skies with a rich and handsome man who cares about her. But she trades this in to find Pete, ending the film at night, in the dark and the rain, standing on the lowly earth. She has traded hope, excitement, fortune, and opportunity for not only the familiar life (which, at face value, there’s nothing wrong with), but a stagnant, selfish life with the man who has been trying to mold her to his expectations and has shown no respect for her opinions or choices.

Pete does not even offer Rosalee anything. Now, I’m not one to bash small-town America or a quiet, less-ambitious life. I have a great deal of affection for quiet lives and small towns, even if they would not be my personal choice. But Rosalee has known nothing else, and just as Pete squanders his chances to express his supposed love for her, Rosalee squanders an opportunity to expand her horizons and experience something new. Hmmm, maybe she and Pete deserve each other after all?

To be clear: I am not slamming guys (or any person) who are less aggressive, who are shy, who are less ambitious. What I am slamming is any sense of entitlement, any belief that someone deserves something that they haven’t actually made an effort to achieve. Pete thinks he deserves to win the heart of the girl he loves, but he does nothing about it, and he acts like an ass when things don’t go his way. THAT is what I have a problem with.

Now, I think the absolute happiest ending for Rosalee would be for her to develop a new hobby, maybe choose a new career or further her education, and strike out on her own, without either of these guys. But if she has to choose one of them … well, I think I’ve made my opinion clear.

"I have made a terrible mistake."

“I have made a terrible mistake.”

Do I still like this movie? Yes. But from now on, I’ll be watching it when I feel like being depressed, not when I want something trivial and mindless.

Seen in this light, the movie takes the “nice guys finish last” cliché and turns it on its head.

But in the end, who is the truly “nice guy”?

3 thoughts on “When the Nice Guy Still Finishes Last: An Overanalysis of “Win A Date With Tad Hamilton!”

  1. I want to see your version of this movie. Also, I am finding myself agreeing with your “most happy” ending, and also wanting to watch the original again. Thank you for taking the time to write this down.

  2. I agree with everything you just said. I had the pleasure of watching this movie the other night on cable TV. I was happy at first because I have heard of it and had the desire to watch it for a while now. At first I knew she would end up with Pete, I could tell that from the first five minutes of the movie, its such a cliche. However that was during the first five minutes of the movie. I had no idea the type of guy Tad was. When I did I found myself, for the first time ever, not rooting for the underdog. And yet the more i started to like Tad, the more Pete started to annoy me. So much so, I wanted to punch him in his face every time I saw him. I found myself praying for three things 1) that Tad turns out to be such a total jerk, so much so I’m rooting for pete or 2) The movie actually doesn’t take a twist and she ends up with Tad…ok and lats one 3) Rosie chooses none. But no She ends up with him and I was crushed. I just found myself pointing out useless pointless things in my head….Whats the point of Angelica? Like wtf, she should have ended up with Pete….no one would be crushed. Tad with Rosie and Angelica with Pete. Everyone is happy. I get that the writers tried to make Tad like the bad with the 6 smiles stuff, but it kinda make me like Tad even more. It just showed how much he didn’t want to lose her, sure it wasn’t good, but Pete called the cops on them. I think its even. And don’t even get me started on the 6 smiles stuff. Sure the idea is cute and all. But Tad just met Rosie, I’m not denying his love for him (I believe in love at first sight), but come on he didn’t know her as long as Pete has. Of course hes not going to know the 6 smile thing. Thats what love is all about, you learn and grow with that person..the more you learn about them the more you love them Whose to say that in due time, Tad would have known about the 6 smile thing. They didn’t even give him a chance. At least he was willing to change. and thats what love is all about too. Finding someone who can make you a better person. And just because they’re best friends doesn’t mean anything. Whats wrong with just being best friends. Its good to have someone who is always there for you. But if they break up, they can potentially ruin their friendship. Whose to say Pete won’t break her heart…? There was no character growth from any characters except for Tad. I don’t mean to sound rude, but by Rosie picking Pete she did the opposite of growing. I know my email is a bit too little too late, but after the ending, I was just surprised I didn’t find more like souls who see the total bullshit of the ending.

Comments are closed.