Celebrity Relationships I Would Feel Sad About, If They Split Up

My friend Firegirl and I periodically discuss celebrity relationships we feel emotionally invested in—the ones where we would feel actual, genuine sadness in our hearts if the relationship dissolved, despite the fact that these are CELEBRITIES and we DO NOT IN FACT KNOW THEM. Here’s my list:

  • Will Smith and Jada Pinkett Smith
  • Heidi Klum and Seal
  • Felicity Huffman and William H. Macy
  • Jamie Lee Curtis and Christopher Guest
  • Sting and Trudie Styler
  • Matthew Broderick and Sarah Jessica Parker
  • Paul Newman and Joanne Woodward
  • Rosie O’Donnell and Kelli Carpenter
  • Ben Affleck and Jennifer Garner
  • Michael Bolton and Nicolette Sheridan
  • Gavin Rossdale and Gwen Stefani
  • Susan Sarandon and Tim Robbins
  • Goldie Hawn and Kurt Russell
  • Brad Pitt and Angelina Jolie
  • Kyra Sedgwick and Kevin Bacon
  • Courtney Cox and David Arquette
  • Tom Hanks and Rita Wilson

It’s hard to THINK of all the celebrity relationships, though. I added Heidi Klum and Seal JUST NOW, and yet they’re one of the couples I feel most strongly about—it’s just that they hadn’t yet come to mind when I was just thinking “celebrity couples.” We need some sort of directory of celebrity relationships so we can go through it systematically playing Sad / Not Sad. For example, I could give a flying frock if Jessica Simpson splits up with Tony Romo, or if Mario Lopez splits up with whatever girl he’s currently cheating on.

The one I think I would feel most upset about is Will Smith and Jada Pinkett Smith.

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65 thoughts on “Celebrity Relationships I Would Feel Sad About, If They Split Up

  1. Marivic

    Felicity Huffman and William H. Macy are one of my all-time favorite celebrity couples. I read a piece awhile back, where they were asked to submit a photo of themselves as a couple, and explain why they chose that photo. They did, and the explanation was “it made us look far more intellectual than we really are” – which endeared me to them even more.

    Reply
  2. McWriter

    Rachel McAdams and Ryan Gosling! I was in a mini-depression when they broke up a while back and was completely ELATED when I saw them BACK TOGETHER in the celeblogs this week.

    All is right in the world again.

    {big sigh}

    Reply
  3. wafelenbak

    Reese Witherspooon and Jake Gyllenhaal would break my heart. They both seem so sweet and so happy.
    Jennifer and Ben can bite it, for all I care. Same for Brangelina. But that’s just because both pairs are so overpublicized. And Jennifer Garner seems like a soulless plastic doll to me. :p

    Reply
  4. K in the Mirror

    One of my favorite couples is Patrick Swayze and Lisa Niemi. They got married the year I was BORN and I would be terribly sad if they ever split up.

    This is a fun topic- are you putting together an interactive directory as we speak? :)

    One that would make me Not Sad is Jennifer Lopez and Marc Anthony. I’m just not invested in them one way or the other. I feel kind of meh about them.

    Reply
  5. t2ed

    What about Pambo & Tommy Lee? I always feel really sad then happy as their relationship ebbs and flows.

    Oh, and Seigfried & Roy of course.

    Reply
  6. Jess

    I would add Ellen and Portia. They are just so cute and they only just got married!

    Also, I’ve been hearing rumors that Matthew may be cheating on SJP… they make me really sad. I hope they’re untrue.

    Reply
  7. Kristi

    Yes…this is pure genious!

    Sting and Trudie Styler would make me the most sad – I read his book a few years back (absolutely no idea why I even picked it up – even though I ADORE him) and reading about the circumstances surrounding the way they met and married really endeared them to me.

    Isn’t it interesting how people we don’t know can get into our hearts like that?

    Reply
  8. Jenni

    Swistle I feel the same way about certain celebrity couples. When Brad Pitt and Jennifer Aniston broke up I was all, “Awww, but they were so matchy and normal and gave to charities! I thought they would make it!” and when Reese Witherspoon and Ryan Phillepe broke up I was, “But what about the kids?” However, when J-Lo and Ben Afflect broke up, I was, “OF COURSE they broke up. Why does anyone care?”

    So silly.

    Gwen and Gavin and Susan and Tim my my faves right now.

    Reply
  9. Astarte

    I’m with marivic – William H. Macy and Felicity Huffman are my favorite couple. I love McCauley Culkin and Mila Junis, too. Will Smith and Jada Pinkett Smith are #3, I think.

    I tend to hold grudges against celebrities who act like morons in relationships, though. I hope AJ and BP DO break up. They both disgust me. I was SO upset when BP and Jennifer Aniston broke up, and then it turns out he was cheating on her?! Oh, no. No, no, no. And I hope it ends with one of them cheating on the other.

    Reply
  10. nonsoccermom

    I was SO UPSET when Bruce Willis and Demi Moore broke up. I still may not be over that. It may be time to move on, yes?

    I am also quite fond of Brad Pitt and Angelina Jolie, although I’m not sure why.

    And of course Will Smith and Jada Pinkett Smith. So cute.

    Fun topic!

    Reply
  11. Anonymous Her

    I hate when any couple breaks up, but especially if they’ve been together awhile. Felicity Huffman’s relationship breaking up would crush me (dramatic much?) and Tom Hank’s relationship ending would make me want to cry as well.
    Tommy and Pam? Not so much.

    Reply
  12. Elizabeth

    It makes no sense at all, but for me it’s Goldie Hawn and Kurt Russell. I’m rooting for those crazy kids.
    Also, I’m still not over Ryan and Reese breaking up. They were just so cute together! Boo.

    Reply
  13. Hillary

    Ellen Degeneres and Portia di Rossi just make me smile, they seem so genuinely in love.

    I also have been stubbornly ignoring the rumors about Matthew Broderick and SJP. Lalalalala — not cheating!

    And I would feel awful if Matt Damon and his wife divorced. I think it’s great that he married someone normal — gorgeous, of course, but normal.

    Reply
  14. Linda

    What about celebrity babies? I read Celebrity Baby Blog and feel like I’m WAY TOO INVESTED in the kids and what they’re doing/wearing/drinking/acting like. I shouldn’t know everyone’s kids’ middle names, you know?

    Reply
  15. Swistle

    Marivic- OH YES, Felicity Huffman and William H. Macy! I can’t BELIEVE I don’t have them on my list. ADDING!

    Nowheymama- YES, Paul Newman and Joanne Woodward! Adding!

    Reply
  16. Vicki

    I am with the Will and Jada crowd. I just love those two. They are so sweet to each other. And then there’s Cheech & Chong. Wait, they don’t count do they? What about Fred and Wilma Flintstone? I like them too.

    Reply
  17. Carmen

    Will Smith is my favourite celebrity EVER. I’ve had a crush on him since his Fresh Prince days. I would be heartbroken if he and Jada broke up – although secretly thinking that now I have a chance! :) I also love Ben Affleck and Jennifer Garner, mostly because I also have a thing for Ben.

    Reply
  18. Erin

    OMG. I have no idea who half those people are! Much less that they are MARRIED SLASH PARTNERED together!

    More evidence to the fact that I have no life. Pout.

    Reply
  19. Kelsey

    I would be sad about many of those, including Jennifer Garner and Ben Affleck. I have always been fond of JG and I was sad when she and her first husband broke up (can’t think of his name for the life of me!). To me she seems refreshingly normal. I know that we can’t really tell, but I think she is one of the least insane celebrities.

    Reply
  20. Alice

    oooh fun! i have to say, i don’t care at ALL about brangelina, but william & felicity, kyra & kevin, goldie & kurt, and courtney & david i REALLY REALLY REALLY want to work. i’m sort of in love w/jennifer garner personally, so i hope she & ben work out just because i don’t want her to be sad.

    Reply
  21. artemisia

    Oh, I’d be sad about a lot of those, too. I’d be devastated if Will Smith and Jada Pinkett-Smith broke up. Why? I don’t know. I guess they both come across as real stand up folks, you know?

    Also, I am totally rooting for Jennifer Garner and Ben Affleck.

    Susan Sarandon/Tim Robbins and Goldie Hawn/Kurt Russell are some of my favorites because THEY AREN’T MARRIED. I am a bit partial to that. ;-)

    Reply
  22. rebcram

    I agree with your lsit EXCEPT the Michael Bolton/Nicollette Sheridan and Rosie O’Donnell/Kelli Carpenter. Otherwise, you are spot on! I do agree with someone above who added Ellen and Portia. I vote yes.

    Reply
  23. ColorCoded

    I have to admit, I was irrationally sad when Heather Locklear and Richie Sambora broke up. Also with Kate Hudson and Chris Robinson. I thought those crazy kids were going to make it. This might seem like a weird one, but I’d be really sad if Kelly Ripa and Mark Consuelos ever broke up. I love them together…

    Reply
  24. fairydogmother

    I’m so with you on the majority of this list: especially Will & Jada, Rosie & Kelli, Felicity and William (Bill?), Kyra & Kevin, and Tom & Rita. I think I would be especially saddened if Tom Hanks & Rita Wilson were to split up, because he reminds me of my favorite uncle personality-wise, and especially with his sense of humor in interviews, etc. Plus all of those couples have been together for quite some time, and despite being celebrities, many of whom have been in the public eye for quite some time, they all seem to be relatively grounded and come across as if they have pretty normal lives even though they have kind of crazy jobs. (Although Kelli O’Donnell has a “normal” job, and is really only in the spotlight by association).

    Reply
  25. fairydogmother

    Also, Jess: me too, re: Ellen and Portia. Although I’ve heard/seen some pretty crappy things being said about them again this week, which I find really rude. As if I get a say in the matter, of course. ;)

    Reply
  26. Jeninacide

    Tom Hanks and Rita Wilson are at the TIPPY TOP of my list. I just love them.

    I would also be sad about Ellen and Portia. They are the cutest! They’re newlyweds though so I don’t feel like I have to worry about them at all.

    Reply
  27. Clarabella

    I’m really surprised no one has wanted to add Tom Cruise and Katie Holmes to this list. Doesn’t anyone care about their “perfect” marriage? Oh my, I’m being sooooo sarcastic.
    Actually, if we were to be doing the opposite list (couples we care least about), they would be at the top of that one. As for this one, I feel irrationally invested in Heidi Klum and Seal’s relationship. I LOVE them!

    Reply
  28. g~

    Ohh, I like Brad Paisley and Kimberly Williams. I thought she was adorable in Father of the Bride (and I think STeve Martin is Huh-larious) and I heard that Brad fell in love with her after seeing her in that movie.
    *sigh*

    Reply
  29. Shoeaddict

    I LOVE:
    -Gavin and Gwen
    -Ellen and Portia
    -Heidi and Seal
    -Kyra and Kevin
    -Brad Pitt and Angelina Jolie

    NO!:
    -Tom Cruise and Katie Homes (but I’d be SO interested!!)
    -Faith and Tim
    -Rosie and Kelly
    -JLO and Marc Antony (or anybody)
    -Michael Bolton and Nicolette Sheridan

    I used to really love Will Smith and Jada Pinkett Smith but I just don’t anymore. I was so sad about Reese and Ryan :(

    Reply
  30. Leticia

    I love Will and Jada, that one would probably hurt most (so dumb and weird to say that). And I was soooo sad about Reese and Ryan. I also really like Madonna and Guy Ritchie and would be sad if they broke up. I know I’m going to sound like a dork but I was soooo sad about Britney and Justin. I know….

    Reply
  31. Bea

    The saddest I ever felt over a celebrity break-up was Brooke and Andre. And now I’d feel sad if she and her husband broke up, even though he’s not technically a celebrity and I can’t remember his name.

    Gwyneth Paltrow and Chris Martin. That’s my favourite – I’d be heartbroken if they split.

    Reply
  32. Lindsay

    Um Leticia? I hate to be a downer, but um, the thing is, Madonna and Guy Ritchie are rumored to be in splitsville. She just turned 50 and I think she has restless legs syndrome if you know what I mean. However her and Guy say no way not true. Last I heard Will and Jada were just as in loooooove as ever.

    Reply
  33. Bird

    Apparently I’m a horrible person, but I think Angelina Jolie is a homewrecker and if she and Brad split up I would be FINE.

    When Jessica Simpson and Nick Lachay broke up I was SO upset. Ditto for Brad and Jenn.

    Reply
  34. Susiewearsthepants

    I’m with you on the Smith marriage. I have followed him since I was a teenager. He has always seemed so wholesome to me. I remember the “Fresh Prince” era and even have some of his music on my Ipod.

    Reply
  35. Sam

    I must add that I would be terribly sad if Gwyneth and Chris broke up, I just like that mix. He seems grumpy, though, doesn’t he? Darn musicians. Anyway, I was just reminded of how much I love Tea Leoni and David Duchovny – they seem so smart and New York and down to earth. (She’s in the new Oprah magazine, the book section, my favorite part of the whole magazine.)

    I was thinking about Ben Affleck the other day, and wondering, does he just SHAKE HIS HEAD over J.Lo? I mean, the big pink diamond, the cameo in her video? What was he thinking?

    Reply
  36. Allstarme79

    This is a topic I don’t think I really cared about until this moment back when, when I thought Brad Pitt and Jenn Anniston were MFEO (Made For Each Other :) ) and I was actually sad at their break-up. But I guess out of your list, I would be sad to see Paul Newman’s marriage fall apart. Though now, I hear he us very ill.

    Reply
  37. Jen in MI

    I don’t know who his wife even is, but I was so sad to hear Morgan Freeman is getting divorced. He seems so stable and trustworthy. Plus, he’s like 70 and it seems if you’re still together at that age, you should be established…

    I do love Ellen and Portia right now-so sweet!

    Reply
  38. Whimsy

    I have a very complicated sliding scale system/ratio that takes the celebrity’s relationship length (i.e. how long they’ve been together), multiplied by the way the celebrity met his/her partner, adds value for if they have kids together (with intensified degrees by how **many** children they have) and then subtracts any weirdness (like, say, dirty picture of the couple in the media) to come up with a VALUE for how much I care about him or her and the relationship longevity.

    This means that Brad and Angelina have a relatively **low** score until you add their many children.

    It’s so complicated, but my brain seems to do the calculation in SECONDS.

    Reply
  39. Emblita

    I think I must be in the minority of people who doesn’t feel sad for Jennifer Aniston or never really cared about her marriage to BP. More invested in Brad and Angelina. Hmm would also be upset if David Duchovny and Tea Leoni ever broke up and Ben Affleck and Jennifer Garner.

    But mostly I try not to get to attached to celebrity couples since their couplings seem to have the lifespan of a fruitfly.

    Reply
  40. Kim/2 Kids

    I can’t believe how invested I can become in celebrity culture. I even subscribed to US Weekly for a year until my 11yo started reading them on the toilet.

    My top couples are:

    Will Smith and Jada Pinkett
    Tea Leoni and David Ducovney

    I was bummed when Jimmy Kimmel and Sarah Silverman broke up.

    Reply
  41. 1hottiredmama

    Oh — Oprah & Stedman. She is so smart to keep her relationship so private and he must be very strong to always let her have the limelight. I hope they keep it together.

    Also yes to Sharon & Ozzy, Will & Jada, David & Tea, Gwyneth & Chris.

    This is fun!

    Reply
  42. Anonymous

    Rachel McAdams and Ryan Gosling have been seen together again. Wouldn’t it be nice if they got back together?

    I love this notebook couple.

    Reply
  43. Annie

    I had a weird obsession with the Witherspoon-Phillippe family back when Reese and Ryan were still together. I was shocked when they divorced, although in my heart of hearts, I always suspected there was a seamy underbelly to that relationship. I love Heidi Klum and Seal too. I do not like Brangelina. Something about them seems very disingenuous to me.

    Reply
  44. Leslie

    Hugh Jackman seems so crazy about his older-actress-whose-name-I-can’t-remember and their adopted kiddies.

    I agree about wanting to believe in the stability of movie’s stalwart men: Paul Newman, Morgan Freeman, Tom Hanks, Ben Affleck, Matt Damon, Denzel Washington. Was illogically disappointed in Easy Reader.

    Reply
  45. Ellen

    I’m with you on Tom & Rita and I also am a fan of Tim & Faith (why not on list?).

    And I may be the odd one out here, but something about the negativity about Tom & Katie actually makes me hope they work. I mean, I thought/think the whole thing was overdone and ridiculous and presented in an immature way, but now they are married, so I think, you know what? I hope they really do stick with it and be happy and raise that kid right, no matter what kind of oddball religion he’s got. Maybe that’s just me, but I get tired of seeing the media wishing divorces on people.

    Reply
  46. Anonymous

    Swistle–
    When I logged on today, I saw a story (truth or not???) that Michael Bolton and Nicolette Sheridan ended their engagement. Which kinda surprised me, because isn’t this their second time together?
    ~Sara

    Reply
  47. fairydogmother

    I was just logging in to my yahoo email account and noticed the “headline” (as if it is any of our business, not to mention NEWS) that David Duchovny checked in to rehab for sex addiction (Hello, I’m totally being part of the problem here). I had to immediate reactions:

    1) I thought of this post and the comments right away, because I knew he and Tea Leoni were mentioned a few times here.

    2) Holy irony, I was just watching a preview for season 2 of Californication, after wondering this morning when the new season starts.

    And now I have a certain Alanis Morisette song stuck in my head, which I guess is an improvement over the incessant pounding on my upstairs neighbor’s door that has been going on non-stop for the last 45 minutes or so.

    Reply
  48. Katie

    Hey, I’m reading your archives. I have a lot of time on my hands today, so thought I’d see who’s still together, 5.5 years after this post.

    Split:
    Heidi Klum and Seal
    Rosie O’Donnell and Kelli Carpenter
    Susan Sarandon and Tim Robbins
    Michael Bolton and Nicolette Sheridan
    Courtney Cox and David Arquette

    Still together:
    Will Smith and Jada Pinkett Smith
    Felicity Huffman and William H. Macy
    Jamie Lee Curtis and Christopher Guest
    Sting and Trudie Styler
    Matthew Broderick and Sarah Jessica Parker
    Ben Affleck and Jennifer Garner
    Gavin Rossdale and Gwen Stefani
    Goldie Hawn and Kurt Russell
    Brad Pitt and Angelina Jolie
    Kyra Sedgwick and Kevin Bacon
    Tom Hanks and Rita Wilson

    Paul Newman and Joanne Woodward were together until Paul’s death.

    Not too bad!

    Reply

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