Pippa Middleton steps out with her boyfriend James Matthews at Wimbledon

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Finally! Pippa Middleton has been dating James Matthews – who is terribly rich, btw – since November-ish of last year. I strongly suspect that there was overlap between “the start of James Matthews” and “the end of Nico Jackson,” the British tabloids really want to marry off Pippa, so they’re not making a big deal about it. No one wants to scare this one off! So Pippa hasn’t been doing pap strolls with James Matthews, and he has not been her plus-one at any charity events. But I asked/hoped for some coupled-up photos of James and Pippa at Wimbledon and here we are!

Pippa and James Matthews came out to Wimbledon on Wednesday for Roger Federer’s quarter-final match against Marin Cilic (Federer won). This really is their first official-ish public appearance together. There’s also a rumor going around that James is going to propose to Pippa in the coming months, although that story sounds like it came from Carole Middleton, so… you know, it might not happen. What do we think of James? I think… he doesn’t really look like Pippa’s type? Her previous boyfriends seemed like buff, athletic types and pretty boys. James Matthews seems sort of small and not that athletic. Maybe he has a really great personality.

Pippa’s dress in these photos is Tabitha Webb. I strongly suspect that many of you Middleton-watchers are correct and Pippa is being paid to wear certain designers, or she’s getting these dresses free on the condition that she wears them to Wimbledon. I don’t really care for this look, but at least she didn’t flash anyone.

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Photos courtesy of Pacific Coast News, Getty.

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57 Responses to “Pippa Middleton steps out with her boyfriend James Matthews at Wimbledon”

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  1. freebunny says:

    British people should never meet the sun.

  2. Jordana says:

    He looks bored. She looks bored. I like her dress. That’s all I got.

  3. RedWeatherTiger says:

    He’s terribly rich, you say? Wellllllll, okay then.

    I like her dress.

    The woman down front looks to be having a lot of fun. 🙂

  4. OSTONE says:

    If you’re a Middleton, terribly rich > pretty boy. I’d be surprised if she locks this one down.

    • mary s says:

      That’s what I thought. $$ trumps all. He doesn’t look very comfortable, and maybe it’s telling that this is their first “official” appearance. Which makes me realize I’m a bit slow, because I kind of thought paparazzi would make an effort to get shots of Pippa’ love interests. No? Do most celebs really stage/schedule all/most of their pap shots? I mean, I remember that bizarre side step thing Posh did that was caught on video– she was coming out of a hotel and sidestepped to get herself smack in the middle of the doors, then proceeded to walk out all cool and nonchalant — and I realized that for all I know they do multiple takes of these little “scenes”. So how did this couple stay out of the spotlight? Did he need to be talked through a pap stroll? Do they know the camera is there? Why do they look so unenthused if they know someone’s taking photos? Celebrity is so foreign to me, I always wonder what is really going on in the background of the construction of their public lives.

  5. Kittahlove83 says:

    What is it about this broad that the Brits love so much?

    • Amelia says:

      We really don’t, tbh.
      The tabloids caught wind of a small bit of public interest after her butt-emphasising bridesmaid dress in 2011 and never let go of their fascination.

      • JudyK says:

        I got so sick of hearing my mom talk about “what a cute butt she had.” Maybe because mine has always been so big, even when I was a toothpick.

    • mary simon says:

      It’s all about the butt.

  6. zinjojo says:

    Kaiser, your question, “What do we think of James?… James Matthews seems sort of small and not that athletic. Maybe he has a really great personality.”

    He has really deep pockets, and that’s what the Midds/Pippa want.

    • Kaiser says:

      Five years ago, the Middletons were hoping that Pippa would land someone with a title! I think they’re settling for “terribly rich” nowadays, but it does seem like everybody’s trying not to spook him.

      • zinjojo says:

        ITA. Right after the wedding, they all thought Pippa would lock down an aristo and/or break out big in media and neither happened. So now they’re settling for very, very rich and hoping this gets locked down soon.

      • COSquared says:

        I still remember those ‘potentially a future Duchess of Northumberland’ rumours. She’s also slipped tremendously in the Tatler list(from top 5 to being in the 100s).

    • addie says:

      ” I think… he doesn’t really look like Pippa’s type”
      Pippa’s type is a man with money.

    • Hudson Girl says:

      ? He’s smart and really, really athletic. He’s a pretty interesting guy with a cool background. His money is self-made which makes him even more impressive. A mellow, nice guy- though, I admit he’s not gorgeous.

    • Thaisajs says:

      Ding ding ding. You are correct.

      That’s a lovely dress, actually.

    • HH says:

      His sunglasses really fooled me. He looks quite attractive with them on. He’s not exactly ugly with them, but I guess I just expected more.

    • Sharon Lea says:

      One reason they seem like a good match because both of their parents made their money. On a personal level, he seems more low key, easy going like her father. I like them together, they seem relaxed with each other.

  7. Aus0611 says:

    The Dress pattern looks like mini multiple Vagina’s.

    • Size Does Matter says:

      You made me scroll back up!

      Pippa looks a lot like Demi Moore to me.

    • mary s says:

      I scrolled back up, too, and I see what you mean. Pippa looks spray tanned. She is prettier than Kate, I think.

      • mary simon says:

        I see the vaginas, too. I think Kate is prettier than Pippa, but Pippa has the better shape, and of course, the Pippa butt.

  8. INeedANap says:

    Hey it’s official! Good for her.

    I was kind of hoping she would keep going with her “lifestyle” career. Not because any of her content was good, but because I was thoroughly entertained.

  9. Betti says:

    She always looks so orange in any photo i see of her – that can’t be a real tan, it looks like she’s overdone it with the St Tropez.

    • Bridget says:

      Combination of real and fake, I think. She spends a lot of time outside training and likely has really crappy tan lines that I’m guessing she uses a lot of fake tanner to even out. Runners tan lines are awful – sports bra/tank tops, shorts lines, and the dreaded sock tan.

  10. burnsie says:

    Looks like James already has the Middleton tan

  11. Whatabout says:

    I actually think they’re already engaged. No way Pippa (or even Carole approving) would move in with him without a long term plan laid out.
    “Okay we get engaged by September, we announce in October, wedding in April.”

    I actually hope it works for her, but long term I could see this falling apart. She seems to like the attention which is fine, but he doesn’t seem to care for it.

    • Betti says:

      I can see this ending as she does love the press attention just a bit too much and given who his brother is he seems to be the opposite of his fame ho sibling and girlfriend.

      • COSquared says:

        I think she’ll tone down press-seeking when she gets the ring. By then her #poshgoals(or it’s near cousin since he’s NM) will have been achieved. The need to be seen(as a posh ‘funemployed’ woman) would be negated by the fact that she’s Mrs. Matthews. And since it’s quite common for very rich men to get life peerages, I’m smelling a Lady Matthews in+/- 30yrs.

    • Sharon Lea says:

      Whatabout – Yes, it seems like they are engaged, in the way they have discussed marriage and she is just waiting for the formal proposal. I agree that she wouldn’t move in with a guy unless it was pretty much a done deal.

    • MinnFinn says:

      I also think they will marry but it won’t work out. After Nico didn’t work out, I kept saying she needs a starter marriage and I think this will be it. I do hope James gives her a hugely vulgar, tacky NM diamond ring. I could see Pippa going the way of Cressida’s mom i.e. 4 or 5 kids with 3 or 4 husbands.

  12. amanda says:

    She looks like skin cancer. But the dress is lovely.

  13. Scal says:

    Where that empire waist is hitting her boobs makes them look funny. Otherwise I like the dress. Cute shape and cute pattern. The waist is just all wrong on her.

    • anna2222222 says:

      Pippa and Kate have fantastic, athletic bodies but so much of what they wear does not suit their body shape. That’s why I always like Kate in McQueen. Even if I don’t love the look, I think they manage to dress her shape really well.

  14. MrsBPitt says:

    I like the dress…it looks cool, and casual!

  15. Cherry says:

    Yay, more Middleton-ladies-at-Wimbledon coverage! Pippa looks cute here. But that new guy of hers… he’s no looker. Good thing he’s ‘terribly rich’ and ‘really into Pippa’.

  16. hey-ya says:

    …I wish her sister n bro in law would just give her a title ( for being sporty or something)…get it over with…let the haters hate..who cares..

  17. Apples says:

    I actually think he is very much her type: tall, lanky, reserved-looking rich (or on his way to be) guy.

    • Mika says:

      James Matthews is really RICH.
      He lives in a $30 million dollar home in West London.
      He the fund manager at Eden Rock Capital management.
      Hi net worth is now probably estimated at $70 million dollars after Brexit.
      He is an Etonian – as poshly educated as one gets.
      He is the son of the owners of Eden Rock Resort in St. Barths.
      James Mathhews is attractive by English standards.
      This is the real deal for Pippa – she cannot do any better than James.

  18. Hopefullyitwill says:

    Hi everyone, I’m new to commenting here so this exciting! Did you notice Pippa carries her clutch the exact same way Kate and Carol does? Nagging Mummy must have drilled that into both of their heads from the time they started playing dress up as babies. “No girl hold it in front of your crotch like so” 😂
    Also the boyfriend looks like a sweaty drinker. You know the type and you can tell he doesn’t know much about the sport because she is explaining to him. Then again heavy drinker, not my type, who cares. Can he make it rain with £1000 notes. Why yes he can!!!

  19. Bridget says:

    Didn’t he do the Norway event with Pippa and her brother? Just because he’s not huge and muscley doesn’t mean he’s not athletic.

    Dr Google says he was indeed a participant at that. And it was in September last year, so it looks like these two got together a lot earlier than folks thought (or really just paid attention to).

    • Tourmaline says:

      Pippa and James Matthews have apparently been friends for a long time, and they’ve done charity athletic stuff together even years ago. He was part of that bike race across America event back in 2014 that Pippa and her brother were part of—-they were raising money for the Michael Matthews Foundation which is in honor of James’s brother who died climbing Everest.

      • Bridget says:

        Just pointing out that no one really knows when these two got together, or when Jackson was really out of the picture; but that considering how close that was to when they actually got together it’s a reasonable guess to think that their relationship started around then. Of course, just a guess. The only reason we found out about Pippa and James (and therefore no more Nico) was just because someone got photos of her leaving his house early one morning.

  20. Talie says:

    He’s rich enough to keep her in a big townhouse in London with a country house, and a free room in a luxury hotel in the South of France anytime she wants.

  21. trehis says:

    Why doesn’t the pattern line up on the part that wraps around the abdomen? For some reason I noticed none of the patterns on the previous dresses line up either. Does it not matter? What is worse, if it almost lines up or is way off….

    • Mika says:

      The patterns no longer line up on her dresses because she alters them and it is done unprofessionally.

  22. Devereux says:

    Yeah, I think she’s compromising BIG TIME. He is not handsome, nothing like Nico or Alex Loudon. And she loved Alex, enjoyed Nico and with James…she’s letting him love her. And that’s fine! Look, if homegirl can’t make her *own* 17 million pound townhouse fortune, she might as well live off of his.

    Yes, they are sporty together. That helps. A lot. And surprisingly, they both look better than before they got together. Pippa’s bone structure is showing through, giving her a more angular attractiveness. He is looking less greasy, less slimy, and that can only be good.

    In the last photo she’s got that fixed grin, thousand yard stare. I think she’ll lock this down. How pleasant/joyful will it be? Eh. How long will it even last? Um.

    I wish her and her marathons and her 17 million pound townhouse a happy life. Oh yeah, and him too.

  23. KiddVicious says:

    I like the vagina dress. That style seems to be the new 1960 Lily Pulitzer (which I love). It’s a great look.

  24. sequinedheart says:

    Its a nice dress but this gal (much like her sister) can make anything look completely dull.
    Pippa has her eyes on the prize (wallet), type or not.

  25. Ji-Yun says:

    On another site it was pointed out that Alicia Vikander and Pippa Middleton look like twins. What has been seen cannot be unseen.

  26. Cee says:

    Does she have the same watch as Kate?

  27. Tourmaline says:

    @Cee–I don’t think so-Kate has the Cartier Ballon Bleu and the style of the numbers on the face of Pippa’s watch looks different.

  28. Starlight says:

    I didn’t realise that James had lost his brother that is very sad. Thank you for sharing.