Tad Hamilton is a big star with the ladies, and after he’s caught doing some naughty things with a lady friend, he’s pressured into re-invigorating his career with a contest for a lucky girl. Rosalee just happens to be that girl. A young wide-eyed fan, she and Tad for an instant friendship, but her friend Pete doesn’t trust him. Ah, the old “Sixteen Candles” formula that has undoubtedly been used before over and over again, and this time around it’s a good variation. Bosworth, a beautiful girl who literally glows whenever she’s on-screen plays Rosalee with much affection and is a great leading character here. She’s someone to root for. While “Win a Date!” doesn’t proceed with originality it accomplishes great characters.
There are a lot of characters here to like including Bosworth who is the small town girl in a big situation and is very charming here. Her smile is out of this world, and she’s just a lot of fun to watch. This is such a chick flick, but I was surprisingly entertained by this piece of sweet fluff. There’s even Rosalee’s best friend Cathy (cute as a button Ginnifer Goodwin) who is a lot of fun to watch here with her odd clothing, and outrageous attitude that made her a lot of fun to watch, Then there’s Tad Hamilton played very well by Josh Duhamel. He’s actually a character himself; he’s not just a big plot device. He has a personality here, and has a really interesting personality to boot. Duhamel is great here and is believable seeing as how he’s an ex soap opera star playing a dramatic actor.
As you would guess, there’s the love triangle between Pete, Tad, and Rosalee, and it’s very engrossing to watch. To say this film was predictable would be like saying the plague was a bad cold. This has to be one of the most cliché films I’ve seen in years with the formula of “Pretty in Pink” with the homely but gorgeous girl falling for a popular stud while her geekier best friend is secretly in love with her. The only problem with this very cliché premise is the ending which goes for the even more predictably traditional of endings, the happy one. Come on, I didn’t ruin anything for you, you know what’s going to happen before you even watch this.
As far as direction goes, it’s all iffy with a lot of badly edited scenes, especially the pivotal one which is basically done poorly. Regardless it’s fluff without a bit of originality in the seams of its screenplay. Why does this pull off the cliché formula? Acting, there’s plenty of good acting as well. Especially by Tophur Grace is very, very, very likable as a leading man and I have to say a lot more enjoyable to watch than Ashton Kutcher; Grace’s transition to the big screen has been smooth yet subtle and this guy can be really good if he chooses his movies correctly. He has a lot of appeal and he’s a great actor to boot. Yes, he can act, take that all you mindless Ashton Kutcher boosters! He’s the everyman in a situation happening a lot; being in love.
Grace is hilarious here and injects a lot of his inept out of place one-liners and quick wit to a lot of the situations here, and he emotes well with his usual facial expressions that are often times just laugh out loud funny. There are a lot of sequences he pulls off flawlessly, and his romantic scenes are great. He’s one of the best love interests I’ve seen in a while, proof in point is the bathroom scene which is not only very well done and delivered but utterly heartbreaking in his desperation. Grace is the best thing here and shines above the rest. It’s his movie, really. There are a lot of funny scenes here that actually made me laugh including the farm scene which made me laugh out loud a lot.
The film, though predictable and cliché is endearing, so I forgave a lot of the flaws and just enjoyed the purely fluffy cavity-inducing story and surprisingly great characterization. I was shocked that I liked the characters so much; it was like a John Hughes film with good characters and depth. We know who we want to root for despite the fact everyone has their meaningful purpose, and no one is ever obnoxious including Gary Cole who has a great walk-on role, Cathryn Hahn as the hot bartender who plays a big role in the story, and Nathan Lane and Sean Hayes who are funny as Tad’s agents. This is great date flick, adorable and very sweet, and you can’t help but smile after you’ve finished watching. While the story is predictable, cliché and full of fluff, this is nonetheless a reliably warm and sweet film with good performances from Bosworth, Grace, and Duhamel.