Olivia Wilde & Jason Sudeikis are loved up in NYC: trading up or trading down?

This looks like a photo shoot, doesn’t it? I’m not saying Olivia Wilde and Jason Sudeikis arranged to be photographed in this “Official New Couple Portraits: Loved Up On The New York City Streets Edition” way. Maybe it was just some weird coincidence. After all, people know that Jason and Olivia are dating – they’ve been seeing each other for about… two months or so. It was about a month ago when Us Weekly reported that they were a full-on couple.

Olivia spent most of the last year sowing her wild oats after her divorce from an Italian (hipster) prince. She dated Ryan Gosling, briefly, and she was associated with Bradley Cooper and Justin Timberlake too. There were other dudes in the mix, but I can’t remember them off the top of my head. It doesn’t really matter – she was just playing around, and none of it seemed serious. But this kind of photo op with Jason? That seems more serious. And I’m not sure how to feel about it.

Jason’s dating history is a bit more complicated. He was married, and the divorce dragged on for a while. While he was dealing with that, some said he and Jennifer Aniston had a fling, although Jason denied it – harshly. Then he hooked up with January Jones for a while, and they seemed to still be dating each other casually when she got knocked up – by another (married?) man, allegedly. Since January Jones, Jason has been playing the field, and Olivia might be his first “relationship” in a year.

At the end of the day, I kind of find Olivia and Jason to be a boring couple. It feels like Olivia went out, played the field, and got disappointed by the lack of opportunities, so she just settled for Jason. Maybe he’s a really nice guy… but he seems like he might have a streak of douche. Oh, well. Good luck, Cockburn.

Photos courtesy of Pacific Coast News.

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43 Responses to “Olivia Wilde & Jason Sudeikis are loved up in NYC: trading up or trading down?”

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  1. someone says:

    meh–there is not much else to say… I kind of dislike both of them

    • vicky says:

      I have to agree with you, meh. I don’t see the appeal of either of them.

    • Kloops says:

      Exactly. Don’t care for either but I do think sudeikis can be funny but he has douche written all over him.

  2. CT says:

    Used to LOVE him, but his taste in women has really ruined him for me.

    Sigh.

  3. Nessa says:

    They look cute together. Although, she is one of the most overrated starlets out there.

  4. Lady_Luck says:

    “cockburn”

    great(and very appropriate nickname) 😀

  5. jazz fabulous says:

    That’s such an awful outfit Olivia is wearing.

    • Ally says:

      That color-blind ‘Little House on the Prairie’ outfit tells me that she didn’t expect to be photographed.

      Ditto re: his ‘In Living Color’ get-up.

  6. Guesty says:

    Jason does seem like a douche. His ex writes for ’30 Rock,’ so I will assume she’s awesome.

    Olivia – I don’t know. No real opinion beyond thinking she has terrible personal style.

  7. TheWayItGoes says:

    So is she and Eva Mendes in some sort of wack ass actress, breakin off a long-term relationship to go A-list ball chasin competition???

    Jason’s funny but he’s giving off so much douche lord swag…it’s irritating.

  8. Kerfuffles says:

    Can we discuss the elephant in the room first…WHAT IN GOD’S NAME IS SHE WEARING? A sunshine yellow polka-dotted sister wife dress for city walks in December?!

    That aside…I think he’s hot & funny, though I’ve read rumors he’s full of himself & kind of a d–k. I think she’s overrated in both looks & talent (13 on House was the WORST! and that JAW!), so I guess they are kind of perfect together to me.

    • TG says:

      I agree if I was going to call the paps I would at least have a better dress on, though I do like the jacket. I have never found her attractive but maybe she is prettier in person.

  9. LadyJane says:

    That dress is a bit summery for NYC in December. She looks freezing. That is all I get from these photos. Brrrrr.

  10. ladyfoot says:

    well they do have good taste in coffee

  11. Turtle Dove says:

    I just clicked to see if there was a picture of her with a mattress on her back. Surprisingly, there isn’t.

    (exits thread)

  12. Talie says:

    Because she ended up being caught up in scandal–The ghost of January Jones will haunt all of his relationships.

  13. Cathy says:

    Gawd, who chooses this womans clothes for her. I haven’t seen any pictures of her that I liked what she was wearing in a long time. That dress is awful.

  14. Eve says:

    I find him painfully unfunny.

  15. lola says:

    They make a cute couple. I love her yellow dress.
    Can’t believe she used to date Ryan Gosling, there are no photos of them together. Wonder why it didn’t work out?

  16. Cali says:

    Her ex-husband was really attractive….

  17. samira677 says:

    Why is it that every time a celebrity dates somebody who is on a lower lever from themselves or their ex or not a celebrity at all the new boy/girlfriend is called a downgrade? Also where did the term “loved up” come from? I hate it especially when it’s paired with photos of people just walking. They don’t look “loved up”. Whatever that is supposed to mean.

  18. taxi says:

    Is she wiping her nose on his jacket?

  19. Kim says:

    Oh Olivia? what are you thinking? Beautiful and talented with this untalented, very unfunny, ugly, egomaniac? She could so sooooo much better.

  20. Heather M says:

    I TOTALLY agree, Kaiser. I think she got married too young and, once her fame blew up, she thought it would be fun to date around since she never really did that…but then she was repeatedly blown off b/c she picked the wrong guys–players who all had just come out of relationships (Timberlake, Cooper) AND/or were at the top of their game (Gosling) and not quite ready to “settle” for Olivia.

    Not to be too harsh b/c Olivia is pretty, but she is inconsistent, IMO. Her gorgeous face can turn from stunning to odd with the wrong hair and makeup, and she gained weight at a really inopportune time–right when she became single.

    Getting blown off that many times in a row makes you re-think your standards. Hence the very average Jason S. She should have just stayed with her prince.

    I think Scarlett Johansson and Olivia should have lunch.

  21. pj says:

    I think she’s a really pretty girl. Amazing eyes.

  22. ToastedSkin says:

    i dont really understand his appeal…

  23. midnightmoon says:

    Jason S was in the first episode of Portlandia (mildly amusing, the second ep wore its welcome out almost instantly) and my reaction was: hmm, who’s THAT? The bit was beyond idiotic, but he had a little sumthin’ sumthin’. For a hot second. Then, yeeeaahhh, not so much. Damn!!

    And oh, girls? Saw what Henry Cavill looks like NOW, as Superman. Ok, all, READY TO SWOON. Oh boy, dat is sum MANFLESH! I think he MIGHT get by the very high standards my ex-bf set… MAYBE. We’ll see.

  24. Sasha says:

    They were together at a KU game I went to last week in Lawrence, Kansas. I guess he’s from here, and a big fan. She seemed really cold and distant, although the sweaty, college-kid atmosphere doesn’t please everyone. He seems to like that type (January Jones).

  25. ZenB!tch says:

    I don’t know who he is. She needs to prove herself.

  26. Pureinsanity says:

    She’s meh without makeup. And he manages to hook up with some pretty women even though he’s neither funy,rich, or hot. He must have a big one.

  27. dirtyblonde says:

    I realize this sounds crazy but I would do filthy things to him. I lust him.

  28. Nan209 says:

    I agree I think he’s a bit douche. It seems like he thinks he is just really awesome.

  29. Jacqueline says:

    I preferred her with Tao. He seemed like the sweet nice guy that could guide her through Hollywood. A wonderful Scorpio. But ya she’s a pisces. They are hard to tie down. I am one no offence. We dont do marriages. (See Elizabeth Taylor.) Olivia and Tao were way better. But ya you never know these people.