A few weeks ago I was leaving WBEZ when my colleague Kate Dries and I started chatting about important things, like how Jenny McCarthy was complaining that her ex-boyfriend, Jim Carrey, no longer communicates with her (Jenny’s, not Kate’s) son. “I kinda liked them as a couple,” Kate said, and we started talking about our favorite celebrity couples, past and present.

Below, please find this ground-breaking discussion. Please feel free to include your own input on your own favorite celebrity couples, either together or now-defunct.

CLAIRE: Okay, so tell me what you liked so much about Jim and Jenny.

KATE: They just seemed like two crazy kids making it work in crazyville. They both were big in the ‘90s and petered out a bit but have legacies. Plus, big, bizarre senses of humor. And now she’s accusing him of abandoning her autistic son? Guys, stay friends. Where have you gone from the days when you shared a bathing suit?

Others that have devastated me: Tim Robbins and Susan Sarandon. Tim and Susan were lifers. Even though I got the sense that maybe he became kind of a jerk as he got older and she’s got a sexy new ping ponger, Bull Durham is basically the best movie (you don’t even need “about baseball” as a qualifier) ever and I love that they fell in love IRL (in real life) even though their characters don’t stay together ITH (in the movie). I was equally saddened by Goldie Hawn and Kurt Russell‘s apparently temporary break-up for similar reasons. Both of these pairs also have kids from outside marriages and really melting-potted the whole situation. If Kevin Bacon and Kyra Sedgwick broke up, I don’t know what I’d do. I think a national day of mourning for the nation would have to be called.

CLAIRE: I was sad about Tom Green and Drew Barrymore because, strangely, I liked Drew more for being with Tom, even though I think it looked to many people like she was slumming by being with him. She’s adorable Hollywood royalty, a reformed wild-child, whereas he was a dorky Canadian not known for his good looks or coolness cache. Even though I wasn’t that huge a fan of his humor, I always suspected that as a person, I’d probably like Tom more than Drew and so I liked that she seemed to have the good enough taste to be with more of a cerebral type of guy as opposed to a traditional rock star. I remember their relationship was REALLY intense, like them giving interviews about how much they relied upon each other emotionally, plus, of course, she saw him through testicular cancer. I don’t remember why they broke up but it bums me out that there are headlines about Drew now “finally” finding love. But she already did! Poor Tom.

I was also really sad about Catherine Keener and Dermot Mulroney.

KATE: Catherine and Dermot! He is so beautiful and she is so talented. I guess they are both both but that’s sort of how that couple broke down didn’t it? Also sad: Courteney Cox and David Arquette.

CLAIRE: What I liked about Catherine and Dermot was that they were both mega-hot to me but in an off-the-beaten path kind of way (I know this sounds like a backhanded compliment, but it just means they were a little more indie darling than A-lister.) They both seemed wry and smart and seemed to match each other in terms of tone — a similar couple to me is Aimee Mann and Michael Penn. I admit I know nothing about them as a couple but based on my superficial evaluation, they should be mated for life! They just seem made for each other, at least as musicians.

Courtney and David — was anybody really surprised when they broke up? Yet, it seemed like their unlikelihood was what bound them as a couple, like there must have been something about him that just wasn’t obvious to everyone else. Maybe he was great at making Courtney laugh. Maybe she was really good at making him laugh. I felt more let down by the obviousness of their breakup than their actual breakup.

I was also really sad about Gwen Stefani and Tony Kanal. First, he inspired her to write “Don’t Speak,” which I think basically rocketed No Doubt to stardom so she has him to thank for that. Also, I just thought they were a super good-looking couple. I think Tony is way hotter than boring ol’ Gavin Rossdale who, I’m sorry, has just seemed so lame to me ever since Bush came onto the scene with their third-rate Brit-pop. Remember the song “Glycerine”? Was that about soap? Give me cool punky Tony any day.

KATE: I was shocked when Courtney and David broke up! Now they seem like they’re friends and co-parenting their progeny with that ridiculous name, which makes me happy. But I was not pleased when I found out that they basically broke up because of his addiction issues and how Courtney felt like she was becoming his mother. And now he gets to go date some young hottie who clearly is not his mother but has also not stuck by him? Unfair.

I used to be really sad about Tony and Gwen circa 1998, mostly because I didn’t buy it: HE dumped HER? Unbelievable. But now all she does is live off her inexplicable millions and have hair so white blonde it’s going to fall out and frolic with her lame but hot husband who may be gay and has secret children out of wedlock, so maybe Tony was onto something I wasn’t.

I know everyone is so happy that Ashton and Demi didn’t work, but I loved them. Especially because I loved her and Bruce and if she couldn’t be with him, at least they could all be one happy weird family together. Recently I rewatched Ashton’s Oprah interview when he talks about how they met and either he’s the best actor ever (no) or it was the real deal, with none of this Tom Cruise/Katie Holmes prenup deal.

Speaking of, I wish I had been old enough to really see Tom and Nicole together. Just looking at pictures of them makes me feel as though I’m staring mirage: it can’t be real but it is! 

Luckily, we all know Iman and David Bowie are aliens sent to spy on us from another planet, so we don’t have to worry about them ever breaking up.

I thought of a few couples that I’d freak out if they broke up:

Jennifer Garner and Ben Affleck

Tom Hanks and Rita Wilson

Beyonce and Jay-Z.

ALSO: OH MY GOD: Johnny and Vanessa!

CLAIRE: I would love to hear your take on any of those three because I don’t really see any of them as being around for forever. I mean I like Bey and Jay, but between the two of them, all that ego, all that money — it seems a little tenuous. Rita Wilson seems nice but every now and then she does something that seems dumb to me, like write an article about how she busted her ass to lose 10 pounds for Bazaar or weigh in on Donna Summer dying (I just didn’t really care for her opinion on either topic.) And I ALWAYS hear that Jennifer Garner and Ben Affeck are on the verge of disaster.Did you think Johnny and Vanessa were 4-ever? I didn’t have much of an opinion on her other than the observations of a.) teeth b.) thin. He seems a little insufferable AND I hear he has a piece/hair extension.I know this sounds nuts but I would be really sad if Joel McHale and his wife broke up. His wife isn’t famous so maybe this isn’t quite fair game to discuss but, while I am one of those ladies who finds him attractive, paradoxically, part of what I’m into is that he’s a family man. I mean, look at this picture of him. It probably sounds terribly traditional and old-fashioned but I don’t want to think of him as a single guy cruising for chicks. Same thing with Conan.KATE: I don’t even know if I would be sad if Beyonce and Jay-Z broke up but I do know that it would knock the earth off its axis because it would prove once and for all that there is no such thing as perfection in any sense. The only bad things to ever happen to Beyonce are threefold 1.) Her dad and mom are divorced 2.) Her dad is a little Williams’-sisters-father-crazy 3.) She basically screwed over her original classic band mates. And we’ve forgotten about all of those because she has like an amazing, perfect personality! Even her Tumblr is perfect! I believe she is sculpted image-wise in a way that we haven’t seen since back when Judy Garland was being plied with drugs to just. keep. going. Anyway, if she got divorce, the whole probable charade would all fall apart, so that’s why I would too.

Rita Wilson and Tom Hanks I’m impressed with because they met on a movie, were both married and were like “We really can’t help ourselves, we know we’re in marriages but our love is bigger than this.” And it apparently was.

I worry about Bennifer because it must be hard to have a well-produced video about how sexy your ex-boyfriends relationship was with his ex-fiancé who just happens to share your name.

Johnny and Vanessa I’ve only been worried about since the rumors; before, they just seemed weird but in a way where they would last forever. Clearly, not the case. But who gets the island? That’s the real tragedy. What are they going to do, share it?

Claire, Joel McHale is wearing a Hawaii T in that picture. And some sort of puka shell necklace. Also his baby is SO bald and it looks like he’s whispering something to it in a creepy way. I will say that I agree that celebrities who are married to “normal” people really sadden me when they break up. Like if Seth Rogen broke up with his wife (who I guess is working on being famous…) I would be really sad.

CLAIRE: You know who should definitely never break up? You and me. I know we are not married or romantic partners nor even hang out that much in real life but still, Kate, you complete….my blog posts.