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01
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02
When Harry Met Sally
"For me, I think this is a definitive yes, they are still together. And the reason, I think that is because they were friends for years first"
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03
Pretty Woman
"Okay, controversial, but I think yes. And the reason is because he didn't feel like he had to be a rich successful guy around her. She has firm morals and beliefs and he respects that. She made him reflect on himself and his job. They'll probably fight a lot but I'm rooting for them"
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04
How to Lose a Guy in 10 Days
"First of all, Andy is 23 years old. How old is he? Like 30? Here's what's gonna happen. She's gonna get a job in DC and he's gonna [stay] in advertising in NYC and while her frontal lobe is still loading, she's gonna be like, let's do the long distance thing. They do that for a while until he loses interest… then they break up"
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05
10 Things I Hate About You
"Y'all are gonna hate me, but no I don't think they're still together. Look, they're gonna have fun together. They're gonna learn a lot about each other and about themselves. They're gonna learn lessons together. [After] she goes to Sarah Lawrence, they're gonna start getting into fights and then they'll break up."
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06
Dirty Dancing
"No, no. What is he, 45 years old? I don't have a crazy stand on age gaps, but I will say when 2 people are in different stages of their lives, it can make or break the relationship."
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07
Silver Linings Playbook
"Okay, now yes. I'm rooting for them. They both struggle with mental illness [and] have a very checkered past, but I feel like they revealed the ugliest sides of themselves and still decided to get together."
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08
Along Came Polly
"It's a no, it's an absolute no. My first thought was his neurotic tendencies are going to drive her crazy and vice versa. He's gonna want some routine in his life and she's not all about that. And that's okay. I don't see you working."
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09
You've Got Mail
"I'm gonna say yes, yes, yes, yes. With some caveats. They're gonna be living their Upper West Side brownstone fantasy together, but they're gonna be dealing with some trust issues, because during the movie they both lied to their respective significant other and had a whole Internet affair."
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10
The Holiday
"Jack Black and Kate Winslet– it's an absolute yes. Now as for Mr. Jude Law and Cameron D…. No. She's so career oriented and works a Hollywood exclusive job and Jude has kids? Yes. Just up and leave. We got 2 little ones. I mean, he could, but I don't think he's gonna. Even though they're hot together."
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11
The Wedding Planner
" It's gonna be a hard pass from me. I'm sorry. Look, I know that Jlo was really hot and people are confused about their feelings, but this relationship started with dishonesty. Yeah, maybe they can survive, who knows? But I think he's gonna drive her freaking crazy."
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12
Forgetting Sarah Marshall
"Okay, so immediately the thought was yes. But my major hesitation here is that there wasn't much time between his 5 year relationship ending and meeting Mila Kunis. Which I guess if you have a chance with Mila, you don't pass it up. So fine. I think they make it okay."
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13
The Proposal
"You guys might be real mad at me for this one, but I'm picturing a Samantha Jones Situation here… He's gonna be like, I want a kid, and Sandra Bullock is gonna be like, I have a lot of childhood trauma so I don't want any children. And ultimately, that's gonna break them apart."
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14
Twilight
"Sorry. Next. No. Absolutely not. I'm not actually gonna analyze this one."
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15
Four Weddings and a Funeral
"I think yes, but mostly because she went and married that old bag who was ugly and she turned around immediately and was like, what am I doing? And then she looked at you, Grant."
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