I hatched the idea to screen 'Say Anything' for our next Sibling Revivalry column last month while Lindsay and I were driving back to New York City from our cousin’s Newport wedding. Peter Gabriel’s “In Your Eyes” came on the radio, and we both sighed. “I love this song,” Lindsay said. “'Say Anything,'” I responded. “Uh… anything?” she replied.

This, of course, opened the screeching floodgates of, “You don’t know?!” and “I can’t believe you haven’t seen!” and “But… but… LLOYD DOBLER!” exclamations that resulted in a bleeding heartfelt description of every possible merit surrounding director Cameron Crowe’s painfully great 1989 debut. I’m not sure which of my fervent re-quotes or euphoric utterances convinced her, but she agreed – right there in that rental car, while listening to the dulcet tones of Mr. Gabriel – to give the flick a shot.

And so we transported ourselves to a world before John Cusack was a household name and Cameron Crowe had Tom Cruise at hello. Lindsay more than appreciated the film’s fresh, awkward take on romance, though she couldn’t help but wonder about some of its finer points. Most pressing: just how long was Lloyd out there holding that boombox, anyway? Here’s the conversation I had with my little sister after her first viewing of “Say Anything,” 23 years after its release.

I feel like you were endeared to Lloyd Dobler (John Cusack) right from the first scene, when he said, "I want to get hurt!" You audibly adored that line.

Yeah! I don't know if I love Lloyd Dobler, but I love his openness for vulnerability. I very much appreciated that statement. Good for him for knowing what it takes and being okay with that!

Lloyd Dobler is pretty infamous as a character who ruins real-life men for women. Do you find that to be true?

No, he's pretty much the standard guy who likes a girl. I don't think there's anything special about that. When a guy really likes a girl, that's the way they behave. He's not special! It's just unusual that there's not such an adverse reaction from the girl to some guy who actually likes her. There's usually a lot of hard-to-get playing.

I don't know, this movie is just about anything but standard as far as Hollywood romantic dramas go -- you see so much of their separate lives and all the awkward moments, even before they get together.

I mean, this is like everyone's middle school or high school relationship. It's pretty standard in that respect. I appreciated the awkwardness of it, I suppose.

Someone asked Diane Court (Ione Skye) why she went with Lloyd to the party…

…"Because he made me laugh!"

You remember the line!

Of course! It was a good answer. I liked it.

Would you do like Diane did and go out with a guy you didn't know at all, just because he made you laugh?

Really? Did you really just ask me that? Yeah, if his net worth was like six times mine and he went to an Ivy League school, of course I would! That's what I try to accomplish on my weekends! [laughs]

So I guess it was a good answer for Diane, but not for you.

Well really, take a step back -- that's actually a very clairvoyant answer from her, because, at the age of 29, I'm finally getting to a place where I want to say, "You know what? All I really need is a guy who makes me laugh." And for her, at the age of 17 or 18, to be able to say that -- and remember, being in high school all you really care about is your appearance, what people think of you, who you're associating with -- so for her to disregard that and give a really mature answer? I'm kind of feeling a little shallow right now.

What do you think of Diane's theory of convergence, about the fact that when a good thing happens, a bad thing happens concurrently?

I love it! I just like people who have a theory of convergence! What is that?! I'm going to have a theory of convergence -- tonight it's going to be about me, rose wine and a hot man! [yelling] Con-ver-gence!

I love how upset you got about the sex scene. Yelling, "What? They have sex in a CAR?"

What the heck was that? It was just weird to me. They barely had an awkward kiss and then all of a sudden they're in the back of a car at Lookout Point or wherever. It's like WOAH - slow down! Teenage sex!

Yes, that super-dramatic, all-encompassing, you-feel-everything-feeling teenage sex.

What? What kind of teenage sex were you having? It wasn't like that for me! It's like the Energizer Bunny and you're like, "Is this what it's like? Oh my God - somebody help me! I'm going to get a concussion from the headboard!"

Maybe I shouldn't bring up the fact that it made me think of the “Titanic” car sex scene…

So instead of Rose putting her hand on the window, we get Diane putting her hand on Lloyd’s face. Which is much nicer, but it was the same palming action.

“Say Anything” – the originator of palmy sex! Accept no substitutes! Lloyd’s friend Corey warns him that everything changes once two people have sex. Do you believe that?

Do I really want to get into this? Yeah, I think it does. Usually it means the guy is going to start treating you like absolute caca.

What would you do if a guy sent you the letter Lloyd sent Diane after they had sex? "I'll always be there for you. All the love in my heart. Lloyd."

See, that's nice. But I'd also be like, "Where's the Cartier?" Well listen, it depends on the guy. It depends on how the sex went, too. If you had robo-bunny rabbit sex, like, I'm not sure, you know? We have feelings, too! We're not just universally in love with someone who sends us a letter! I might not want that the next day!

Point taken. What about the famous line, "I gave her my heart and she gave me a pen."

I like that. Usually it's inverse. I gave him my heart, he gave me herpes! That's the modern day version of this.

I loved your reaction to the boombox over the head scene. You were all, "She didn't even get up after he went to all that trouble?"

I'm just saying, wouldn't she be curious to at least see what he was doing? Like, was he in the back of the car waiting for her with a blanket wrapped around him, shaking again? I don't think that's accurate. Wouldn't you at least poke your head out the window? That's just so weird - it was very non-movie-like, I'll tell you that much.

Maybe that's why the scene has become so iconic.

How long do you think he waited out there? Do you think he had the song on a loop, or he had to keep rewinding the tape? And he stood out there for, like, an hour and his arms were so sore he couldn't even drive home? What do you think? It's killing me!

I think he played it once and then went home. Lloyd can be a very succinct guy like that. So the last scene. Damn, do I love this movie's last scene.

Me too. Because I always sit there in planes and wait for the beep! I don't like taking off. It was a great scene.

What would you do if a guy said he essentially wanted to devote his life to taking care of you, like Lloyd said to Mr. Court?

Yeah, that makes vomit rise in my throat.