Ashlee Simpson is engaged to Diana Ross’ son, Evan Ross of ‘Mockingjay’

Ashlee Simpson

I really don’t know what’s going on with Ashlee Simpson these days. Professionally, she’s not doing much of anything. She hasn’t released an album in several years, and the highlight of her IMDb profile is still a mere 13 episodes of that Melrose Place remake. Ashlee is kind of a mess. I remember wondering why she was all tarted up like a Real Housewife at the recent LA premiere of Catching Fire. She was there with her then boyfriend, Evan Ross. He’s the son of Diana Ross and will play Messalla in the upcoming Mockingjay movies. Poor Messalla doesn’t know what’s coming to him.

Ashlee has had an interesting love life over the past few years. She and Pete Wentz divorced, and she moved on to Boardwalk Empire‘s Vincent Piazza. In early April of last year, Ashlee was said to be “determined to marry” Vincent and “have his baby.” They broke up shortly thereafter, and Ash quickly moved onto Evan. Now Ashlee has posted a engagement announcement on Twitter with a halfway decent shot of her ring. Nice Instagram filters.

Congrats? I mean, really. Congratulations to Ashlee and Evan. I don’t know anything about the guy, but he must have money if his mom is Diana Ross. I imagine Ashlee is still earning some residuals off her old music. I wonder if she still has a drinking problem and if this ultra-blonde Housewife look is merely a phase. I worry about Ashlee and hope that she is well.

Ashlee Simpson

Ashlee Simpson

Photos courtesy of WENN

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73 Responses to “Ashlee Simpson is engaged to Diana Ross’ son, Evan Ross of ‘Mockingjay’”

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  1. Anna says:

    Ever since the beginning of Evan’s “career”, I always found him exceptionally creepy looking.
    Congrats to him and Ash, but I don’t really see this lasting a while. it seems so rushed

    • rin says:

      Yeh, it’s the eyebrow situation. Couldn’t be with a guy with those eyebrows.

    • GIRLFACE says:

      I agree the eyebrow situation plus the overall facial weirdness is what makes him creepy.

      • Christo says:

        Yes, he has his mama’s eyes. I keep waiting for him to break into “Ain’t No Mountain High Enough”—and put on a wig and blue eye shadow.

      • ceecee says:

        I’m 15 yes older than him and it creeps me out to say i always thought he was cute

    • Florc says:

      I don’t know about him, but she seems very unstable. This is likely to not last and will end badly. But best of luck.

  2. Zbornak Syndrome says:

    Child needs to pull his pants up before he does anything.

  3. Lucy2 says:

    She seems like a mess these days.

    • blue marie says:

      Yeah, but I think she might have always been? I mean, it can’t be easy to be the less successful Simpson. I dunno, I’ve always felt sorry for her so I hope she’s happy.

      • Green Girl says:

        I always feel sorry for the siblings of big stars who also try to make it in Hollywood. I wouldn’t want to be “the other one,” that’s for sure.

    • Meaghan says:

      I haven’t really heard much about her lately, any good stories I missed out on indicatineg she is a mess?

  4. BettyBlue says:

    She seems happiest coupled up. At least they’ll have cute kids. Oh wait, I completely forgot about the infamous rhinoplasty. It’s so hard to make predictions about Hollywood kids…

    • Sassy says:

      Hard to predict what the kids would look like, since Evan is half Norwegian. His late father was a billionaire also. Who cares if he has funny eyebrows!

      Ross met her second husband, Norwegian billionaire shipping magnate Arne Næss, Jr. in 1985 and married him the following year, later having boys Ross Arne and Evan Olav

  5. Amanduh says:

    Anyone else getting a Ricki from “My So Called Life” vibe from this guy??

    • mickey says:

      Thank you! That was going to drive me nuts all day! (Because I have no life.)

      I had a similar experience years ago watching The West Wing. The real Ricky was on one (maybe two) episodes (near the end of the series).

  6. DD says:

    He’s extremely interesting looking. Hot androgyny.

    • Frida_K says:

      I hear you…though I can’t decide if it’s creepy or sexy. Maybe a bit of both.

      Of course, as soon as he hitches his wagon to the Simpson clan and to Alcoholee, I mean Ashlee, that kind of takes the intrigue down a notch.

  7. Meredith says:

    His dad was Diana Ross’ second husband, a European industrialist. Scads of money. He died in a mountain climbing accident when Evan was a kid . Very sad. But Evan has lots of money from Dad’s side – never has to work in his life.

  8. Esmom says:

    I agree this is worrisome. I’ve always had a soft spot for her for some reason, I guess because her parents always seemed to be so obvious about treating her as second best.

    Hopefully her son is OK through all this stuff, too. Presumably life is more stable when he’s with dad?

  9. miller says:

    he’s incredibly creepy looking. he ACTS weird too. i’ve seen him in 90210 and jeff, who lives at home and in both movies he gave off such a creepy vibe- something i think was unintentional as the characters were not meant to be creepy. he has crazy eyes too ugh. i can’t be the only one who thinks this, right?

    • Latisse says:

      GAH SUCH crazy eyes! Thank you, I knew a girl like that in school, every time I looked up she
      was like ( o ) ( O ) , it was super creepy!

    • AlmondJoy says:

      Lol @ crazy eyes! He has eyes like his mother. I find her to be beautifully strange-looking as well. Its hard to explain.

  10. neelyo says:

    I can’t imagine Diana Ross is excited about being related to the Simpson clan, though she can out-diva all of them, including Papa Joe.

  11. Latisse says:

    …d-does he tweeze his eyebrows?

    • Esmom says:

      Possibly. But it looks pretty natural. I give him a pass since he’s nowhere near Jesse Metcalfe or Billy Zane levels of obvious manscaping.

  12. Ag says:

    Hmm, I didn’t realize she was no longer married. Those crazy kids these days. (That pic she used to announce their engagement is very creepy.)

  13. Leah says:

    Evan has plenty of money. Not only from Diana but his dad was a european billionaire. There is probably more money coming from his dads side than his mom. Pretty sure Evan has been engaged before so they both seem like they like to get engaged to whoever they are dating. Doubt this will last.

  14. Moec1 says:

    Wow! Barely recognized her! Girl needs to stop jacking up her face! Looks plastic and like it doesn’t move. She use to be such a cute girl too!

  15. serena says:

    Doesn’t he look like JLo’s boytoy Casper Smart? lol

  16. Kenyan247 says:

    I saw him once on a movie called ATL ft T.I and he was the cutest thing everbut now the wannabe goatee and the eyes does nothing but make him look like a serial killer.And thus Simpson chick…i only know one Simpson,this must be the ugly quackling.

    • YoungHeartOldSoulNewView says:

      I remember him in that, he was still more of a kid then though. The latest major movie he was in was the TLC biopic on VH1 where he was horribly miscast as Dallas Austin, a tall, lean, brown, sexy-in-an-edgy-way music producer who has a child with Chilli of TLC. Hated him in that movie. But for some reason, even though this pairing is VERY random, they kind of do look like a cute couple. Kind of.

  17. beth says:

    Does he look like Caspar Smart or do I need new glasses ? (forgive me, I’m 40!)

    • miller says:

      YES omg i wrote earlier that he gives me a creepy vibe and now i totally see one of the reasons why. he’s totally casper smart with crazy eyes which makes him so much more creepy. i know he’s diana ross’ son and she’s an icon but damn they just don’t work for him like they do for her.

    • Mitch Buchanan Rocks! says:

      You called it 🙂

  18. moptop says:

    Um, I think alcohol is the least of her problems.

  19. Kiddo says:

    It makes sense. He is in the shadow of his mega famous mother and she is in the shadow of her more famous sister. Mazel tov.

  20. db says:

    wow, I’m surprised at some of the comments. I don’t much about this kid, but he doesn’t look “creepy” to me — but maybe he plays one? I don’t know. He dad was Ross’ second husband, Arne Naess, a billionaire.

  21. Quinn Parker says:

    Ugh. She seems like she needs five years of therapy and dating probation. Girl CANNOT be alone for two seconds. Actually, neither can Jessica.

    • gritsngreens says:

      Murphy- and wasn’t there a blind about this Ross kid being gay as can be? That the talentless Simpson is hanging on b/c of money and drugs?

      Hollywood life makes me feel so much better about my own. 🙂

  22. Murphy says:

    Just say it like it is–Jessica and Joe cut her off b/c she won’t quit the drugs. So she’s been trying to latch on and finally caught a fish. Kudos to Piazza for figuring it out (eventually)

  23. taxi says:

    He looks like Michael Jackson to me.

  24. Lucy says:

    While sometimes I can see why some people describe others as “creepy-looking” (most of us have done it at some point), I never really understood why so many of them do it as if the other person (the one described as creepy) could do something about it. Like, what’s up with that?

  25. Asiyah says:

    I have a soft spot for him because of the movie “Mooz-lum.” I don’t like her, though, and I wish he had better taste.

  26. RobN says:

    I generally judge her mental state by how much she weighs. Looks pretty healthy right now so I’m guessing no drugs and less partying. Maybe he’s a good influence, although he’s got that rich kid never has to work vibe going.

  27. Jordan says:

    He sets my gaydar off for some reason. I had never heard anything about him, til he started dating her, so maybe it’s a relationship based on things other than love.

  28. Holly Hobby says:

    I don’t know too much about him other than he is Ms. Ross’ son. I do remember a rumor that he was close to Michael Jackson and there were insinuations in the net that MJ was “fond” of him too when he was a kid.

    She should fix her problems before committing to another relationship.

  29. reba says:

    This guy just oozes Michael Jackson! Maybe because MJ had so much work done to look like Diana Ross??

  30. LAK says:

    Arne Naess jr’s wealth dwarfed whatever money Diana Ross had/has. His money came from shipping and oil.

    Even if he inherited an equal share with his other 6 siblings, this kid probably has more money than his own mother.

    Edit: i keep forgetting that MJ had so much surgery to look like Diana Ross. All i see in this kid is MJ.

    • Shazz says:

      Actually Diana Ross just had 2 sons for Ness so he wouldn’t be splitting it with the other Ross siblings. Btw, there are just 5 of them. Diana had 3 kids with her first husband (well, technically 2 cuz the oldest is Berry Gordy’s) all girls, and the 2 boys for Ness.

      • truthSF says:

        LAK was talking about his father’s kids, Evan is one of 7 kids that Arne Naess Jr. had:

        Leona Naess, Ross Naess, Louis Naess, Katinka Naess, Nicklas Naess, Christoffer Naess, and Evan Olav Næss, but he goes by Evan Ross professionally.

  31. amp says:

    She looks pregnant to me in the top photo.

  32. Shannon says:

    Ashlee cannot get over being in Jessica’s shadow. I don’t understand why she’s tried to “make it” in the same industry. You would think she’d want to do something her sister has never done.

    That hair is so dry, chop off the ends and get some deep conditioner honey! This is a PSA: long hair is not hot when it’s in terrible shape! This goes for everyone! No, your extensions are not hiding your horrifying 4 inches of split ends. If you can’t take care of your hair you have no business growing it out. Bleaching = not taking care of your hair, FYI.

  33. Snowpea says:

    Ashlee seems as plain as a pumpkin and the most boring person on the planet.

  34. Jennifer12 says:

    She seems to be a mess and a permanent teenager. Her “baby love”? I hope Pete Wentz is doing most of the raising of their kid, which he seems to be. You never see Ashlee with their son, but Pete is always with him.

    • Boxy Lady says:

      I think the “baby love” thing was a nod to Diana Ross. It was a song she sang with the Supremes. If it weren’t for that connection, yeah, I would totally think it was a weird thing to say 🙂

  35. rep says:

    He seems desperate and so does she. And Yes he does look creepy with that goatee. She is so basic and what some would call thirsty. She is definitely in it for the money. He is trying to be famous.

  36. i says:

    Ms. Ross must be pretty upset about this as she could really sing and had an amazing career as both a musician and actress. Ashlee Simpson is a nobody, she was caught lipsyncing, (clearly can’t sing) hasn’t any real acting experience and doesn’t even have aspirations to do better.

  37. Baskingshark says:

    Is that Ricky from My So-Called Life?