Pippa Middleton’s fiancé has been obsessed with her for the past ten years?


Here are some more photos of Pippa Middleton from her half-dozen pap strolls last week, following her engagement announcement. I think it’s half-and-half with the pap strolls… the paparazzi descended on Pippa’s home after the engagement announcement, so she was always going to be photographed. But I also think she was having fun with it, being back in the spotlight and getting attention for “landing” someone Terribly Rich™. Plus, I do like seeing this dog. I’m pretty sure this is Ella, James Middleton’s beloved cocker spaniel (and relative to the Cambridges’ Lupo). James Middleton and Pippa have long shared a flat in London, although I keep hearing that Pippa is moved much of her stuff into her fiancé’s luxury home already. Maybe she was just dog-sitting for her brother then.

Anyway, the Daily Mail had an interesting write-up on Pippa’s engagement, and it’s worth discussing. We already knew that James Matthews and Pippa had a brief romance back in 2012, something that lasted for just a few months. We already knew that Pippa and James had known each other for years beforehand too. But did you know that James was secretly plotting to marry Pippa all along? That’s what the DM’s “sources” claim! Some highlights:

James wooed Pippa with expensive gifts. He bought her “a £250,000 art deco engagement ring with a three-carat Asscher-cut diamond at its centre” and “the £14,500 Cartier Ballon Bleu watch.” He’s also buying her “a £100,000 classic car,” and he’s “enlisted the help of high society dealer Ed Lovett to source a ‘sporty, sexy number’ for his fiancee to zip around London in. A 1960s Mercedes Pagoda, like the one driven by Kate Moss, is apparently top of the wishlist.”

James wooed the whole family: Before he was even with Pippa, he would fly the whole Middleton clan to St. Barths… on his £3 million private jet.

James has been pursuing Pippa for a decade: “The Mail on Sunday can reveal that James has been patiently pursuing his bride-to-be for a full ten years – strategically planning his advances while waiting for Pippa to outgrow the eight-year age gap between them. And while other privileged young men might busy themselves with a series of girlfriends, James used the time to build a business and a fortune so vast he could treat her like a princess.”

When they met a decade ago: “Friends say he knew Pippa was the one from the moment she stepped foot on St Barth’s and confidently introduced herself to him. But with Pippa taken and an eight-year age gap between them, James was forced to bide his time. Though he always stayed in contact, he had to watch from afar for six long years as Pippa finished her university studies and wrapped up relationships with two serious boyfriends, banker JJ Jardine-Paterson and cricketer Alex Loudon.” A friend says: “You got the sense James was holding out for the one, and that was Pippa… The truth was, the only girl he really wanted was Pippa. He always carried a torch for her.”

[From The Daily Mail]

Is this creepy or fine? I’m going back and forth on it. Part of me thinks that it is sort of romantic to think that this guy has been holding a candle for Pippa all this time. But another part of me feels like the DM is painting him as sort of a stalker.

Also: it’s been said that modern romance films often fail because there are really no barriers to love nowadays, that anyone can fall in love with anyone, that anyone can marry anyone, that there is no “struggle.” So the “barrier” of an eight-year age gap seems… forced. James met Pippa when she was 21 or 22, let’s say, and he was 29 or 30. While that’s a significant gap in experience and worldliness, by the time she was 25 or 26, everything would have evened out. My point is that an eight-year age gap really isn’t a huge deal and back in 2012, when Pippa was 28 years old, it should have “stuck.” I mean, if it was really meant to be, why didn’t it stick? There’s some other reason besides their ages.


Photos courtesy of Fame/Flynet.

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88 Responses to “Pippa Middleton’s fiancé has been obsessed with her for the past ten years?”

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  1. jeanpierre says:

    That doggie <3

  2. mytake says:

    My husband and I also have an 8-year age gap — and married at 32 and 40. Gotta say, I kinda agree with Pippa and James; I don’t think our marriage would’ve lasted if we got married when I was 25.

    Also, sure, I can see why people would think James is a stalker. But, if it’s true, I admire his measured tenacity and patience. And forward thinking! That’s some Jedi-level planning, right there.

    • PGrant's Girl says:

      PGrant and I are nine years apart. I’m 39 and he’s 48, but we first met when I was 24 and he was 33. There’s absolutely no way things would have worked out back then, because I was a hot mess and it would have eventually imploded in spectacularly dramatic fashion. So I can buy that the age difference mattered to James when Pippa was still 25-26. However, I totally don’t buy that he was waiting longingly on the sidelines for her to “grow up.” This story makes him seem so creepy! Middleton PR is a fail.

  3. AG-UK says:

    She is Boring…

    • sensible says:

      And a bit sexless.

      • Sabrine says:

        I wouldn’t doubt her fiance finds her ability to climb mountains and succeed at other strenuous sporting activities quite sexy. I don’t think she “settled.” She hasn’t been able to wipe that smile off her face since they got engaged and the body language between the two is very good.

      • Denise says:

        Nailed it. No sexy there.

    • Sarah says:

      Yes good on you for pointing that out. Such audacity she has! It is her responsibility to ooze sex at all times of the day, what with being a female and all.

  4. Red Snapper says:

    This is Middleton pr to convince people that Pip isn’t settling. Its a love story of the ages! Sounds better than left on the shelf Pipster grabbing the first Terribly Rich guy who was willing to put a ring on it. This is a starter marriage.

    • Lyssa says:

      I agree. Middletons are totally trying to paint a picture that she didn’t settle. She did.

      • Zimmerman says:

        I think it is Middleton PR, but more like trying to make her seem like some precious gem that was fought for instead of the gold digging and title hunting that was really going on from the Middleton side.

        That being said, I do hope they are evenly matched and have a great marriage. I don’t wish them divorce or unhappiness

    • BDA says:

      I completely agree.

    • Vava says:


    • notasugarhere says:

      I don’t know about starter marriage, but I do lean towards Middleton PR to try to make folks forget she’s never dated a poor man. The sights were always set on someone with a title and hefty bank balance

    • Dani says:

      I wouldn’t consider him settling at all, actually. He’s cute, wealthy, well employed and they have a lot of hobbies/friends in common.

      • Bridget says:

        I know we should be pointing and whispering that Pippa is ‘stuck’ with someone without a title, but she’s with someone who seems genuinely well and matched and happy with.

  5. Grace says:

    Hahahah! Obvious PR is so obvious! I found it hilarious and tragic at the same time. Having found a man/woman with whom they want to make a commitment is never enough for these people. They always HAVE to shove vanilla fairycake down everyone’s throat.

    • addie says:

      Agreed. Really obvious. Wish Pippa would just disappear into her new life; we really don’t need to know anything or hear about it further.

  6. It'sJustBlanche says:

    When I was in my 20s a guy eight years older sounded ancient. Even now, if I were single, I’d probably keep it at five years either. Way.

    • notasugarhere says:

      Her ex Nico was 6 years older. I don’t see her rejecting a man 8 years older merely because of age.

  7. Yenta NYC says:

    The Midds overdid it and the story they are promoting seems absurd. Ma Midds is afraid it will look like 32 year old Pippa settled for a guy she rejected 4 years ago that was still willing to marry her. Luck Pippa rescued from spinsterhood and still lands a rich guy would be my narrative.

    • Sarah says:

      With all the gifts, they made it sound like Pippa was bought and paid for. I found that disturbing.

  8. kittenhotel says:

    I really don’t buy this story.

    Not to be mean but Pippa isn’t interesting enough to be stalked.

    • Grace says:

      Are we really to be believe, a rich finance guy, who doesn’t look like he’s been practicing celibacy whatsoever, held a secret torch for his non-interesting bride-to-be for ten years? Sure. I think stranger things have happened. But printing all over DM just cheapens every romantic angle ever intended.

      • LAK says:

        It’s all so unnecessary. People have been known to date briefly, come back together after a time and make it work the second time. See Giselle and Tom Brady. No need to spin a fairytale romance out of it.

      • Bettyrose says:

        I don’t even think they were going for fairytale romance. They’re barely concealing the subtext, he’s a guy who builds fortunes and collects luxuries, like the sister of the future queen. I bet he’d spend ten years pursuing a rare automobile too.

      • LAK says:

        Bettyrose: hadn’t thought of that. The definition of a trophy wife where her value lies in her connection to royalty as opposed to outstanding beauty or wit.

      • Grace says:

        @ Bettyrose, now I see, thank you. It’s all about connection with that one.

      • bluerunning says:

        But then, what would have happened if she’d “landed” one of her ex’s? Would James have just crept off into the night, heartbroken and forever alone? Or married a doppleganger, forever in love with a woman he can’t have? It seems like he’s just assumed that eventually it would work out, when Pippa was making a concerted effort NOT to marry him.

        Either way, yeah this comes off, at the very least, as kind of weird? But I guess she’s got her rich husband and he has his dream girl (??)

  9. piratesgal says:

    that dress is fabulous

  10. Micki says:

    Her engagement ring must be gorgeous. I like assscher cut diamonds. On the other hand I don’t care for Mercedes Pagoda.

  11. What's Inside says:

    I think she hit the jackpot. He may not be eye candy and he may be a bit boring, but what the hey, he can certainly pay for her upkeep which I guarantee will include lots of dermatology and plastic surgery appointments in the future to fix the skin damage and ageing and so forth….. Now she can keep up with Sis.

  12. bettyrose says:

    It’s nice to see a story about her being the sought after one, rather than the gold digger (uptrader?). She is after all the aunt of the heir. Why wouldn’t a tacky nouveau riche suitor go all out to land that. Good for Pippa!

    • Olenna says:

      No offense, but I think the phrase “nouveau riche suitor” works both ways in this case. IMO, this an *arrangement* that benefits the both of them. Not to mention, her transition from Nico to this guy was fairly quick.

  13. Whatabout says:

    Ohh you forgot to mention the juiciest bit of gossip in that article. He was dating Pippas good friend up until September of last year and broke up with her around the same time Pippa broke up with Nico.

    I have theorized that these two were friends with benefits for years and when she realized things were going south with Nico she met up with many of her exs to test out the waters. There’s pics of her with Alex Loudon and that Greogory guy in September. I think James was the only one she realized would go to the altar with her.

    • graymatters says:

      I hadn’t thought of that! I think you’re onto something. I wonder what the gossip within those circles is about this relationship. That’s probably juicier than anything we come up with.

    • Sharon Lea says:

      Whatabout – good catch about him dating her friend, I totally missed that! And I also totally think she was meeting with exes to see who might be willing and able to become her next boyfriend. I remember seeing pictures of her with those other guys.

      The PR spin is so odd, so was Pippa the ‘party girl’ or the ‘airhead’ when they first met? Why would she need 8 years to improve herself???

      • Whatabout says:

        I wonder if the ex/Pippas good friend will
        get an invite to the wedding?!

      • Sharon Lea says:

        ha, and Nico, will he get an invite? Its a wonder the Daily Mail hasn’t shown him dating.

  14. graymatters says:

    I remember when the Cambridges tried to set her up with Guy Pelly and he said something to the effect that he wasn’t rich/titled enough for her. Maybe that was JM’s problem back in the day — at that point, if there had been an agreement for the KW wedding, Pippa would have expected someone closer to court. I just keep thinking of Mrs. Bennet exclaiming that with dear Jane having landed Mr. Bingley, it will throw all sorts of rich men into the paths of her other girls.

    • LAK says:

      Oh my goodness, i thought i’d imagined that quote from Pelly. I thought it was funny that Pelly ended up marrying an heiress of his own.

      • graymatters says:

        I’m weirdly rooting for the Pellys. He can be a bit of an ass and I loathe his cavalier attitude towards drunken driving, but she’s more interesting than she appears at first glance and I think they both will do well in this quasi-arranged union. I find myself wondering if she’s expecting yet.

        I think Pippa will be pregnant by New Year’s 2018. I wonder if she’ll downgrade her exercise to 5K runs for charity in that event, or use it as an opportunity to quit the extreme sports altogether.

      • Bridget says:

        I’m the opposite – I’ve always found Will & Harry’s group of friends to be icky, and think Pelly’s wife could find someone more pleasant.

  15. notasugarhere says:

    BRF historical note, Charles and Diana married 35 years ago today.

    • Citresse says:

      It feels like Diana has been gone 35 years.
      As for her memorial at Althorp, I hope Charles Spencer kept his word with regard to maintenance.

  16. Clare says:

    The best thing about this is that the Cambridges will now be related, by marriage, to Spencer Matthews.

    For those not familiar with trashy British reality tv show stars – he’s the scum bag who dates/cheated on basically everyone on Made in Chelsea, and then got thrown off our version of I’m a Celebrity Get me Out of Here for being addicted to steroids. (Not mocking addiction, btw, just amused by the scummy-ness of it all)

  17. shoochai says:

    It sounds like the plot to one of those smutty “billionaire” romance novels I read. Creepy billionaire creeps on girl creepily, but girl finds him “charming” and “protective” instead of “creepy” and “predatory”.

    Edited to add: Also, Jay Gatsby.

    • Olenna says:

      Ha! I’ve been a book snob my entire adult life, but I recently started reading paranormal versions (rich vamp, shifter, etc., LOL!) of the billionaire romances with my new Kindle Unltd subscription. OMG, that ish is addictive!

      • shoochai says:

        Super addictive! I just started reading them about a year ago myself, and it all started because I signed up for Kindle Unlimited! Crazy. You should check out the site “Smart B*tches, Trashy Books” – they always have fun perspectives, reviews, and recs.

      • bluerunning says:

        I’m with you!! Book snob until I had fast, easy access and now it’s such a slippery slope! It’s all so trashy but I can’t say no!

      • Olenna says:

        @soochai, thanks for the site tip! I see they cover sci fi/space opera, my other favorite genre!
        @blue, trashy is fun and I’m sliding the down slop with you! Ice Planet Barbarians, here I come!

      • LAK says:

        Ladies, don’t go there. Soon you’ll be in Barbara Cartland Regency romances and pining for your very own Prince Charming.

        All these books are the reason real life romance sucks……heightened expectations that no real life Prince Charming can ever hope to meet – see Prince Charles and Diana.

      • bluerunning says:

        @LAK Oh trust me, I know! The boyfriend just suggested we get take out pizza and watch CNN for our date nigh tonight. Nothing says romance quite like political commentary and greasy carbs.

      • Scotchy says:

        I am a lover of all the smut and trash!!! Thank god for kindles as back in the day I would make book covers to hide the horrible titles and somewhat risqué cover “art”

    • Cee says:

      So this could be a very vanilla 50 Shades? LOL

    • LAK says:

      Aka Edward and Bella from Twilight.

      Though in that situation, someone with alot of time on their hands edited this riposte to youtube.


  18. JustVisiting says:

    There is age difference and there is maturity difference. That article seems to forget this.

    And yea. This is complete PR and it’s the start of all this stuff hilarious preemptive and rewriting coverage. Give it a few weeks. We will see things coming through the cracks. Otherwise this style article wouldn’t be bothered with.

    • LAK says:

      The age difference thing is the polite way for this writer to say Terribly Rich James found her immature and waited for her to grow out of that immaturity. Apparently, if we are to take article at face value, she finally matured at 31.

  19. Betti says:

    Really – come on Middleton PR do you really think we’re that gullible. Its very likely the other way around – Pips stalked him, much in the same way Chutney stalked Chopper for 10 years.

    • Grace says:

      It’s possibly the guy has been wanting to marry her, or somebody like her, for quite a while. She’s the future queen’s sister after all. But to make him sound like a lovesick puppy in the ways DM described is selling tall tales from neverland.

      • als says:

        Maybe they are trying to show us that there are other ‘stalkers’ out there like Kate and look what a happy ending they all get!

  20. Cee says:

    This makes it sound as if James Matthws was a Kate Middleton and Pippa was having fun in her 20s, seeking a bigger fish in the pond.

    The list of things he gave her is tacky – did he buy her love? Because it sure looks like it.
    Also, nice confirmation on Pippa’s watch – I knew it looked similar to Kate’s!

    Anyway, I’m sure Pippa is thrilled to have someone who loves and wants her this hard. She’s happy and satisfied, and that’s a lot to accomplish. I wish them the best.

  21. stella says:

    OK first of all that ring isn’t worth 250,000 pounds. This was an estimate by some Daily Mail expert of a flawless D color ring of that size. Hers is NOT a flawless D no way. I know my diamonds and it is not sparkly or white enough. It could be worth even half or much less than that depending on what color grade it is, and how many inclusions there are. It is NOT a flawless D, sorry.

    Secondly, my theory is that he was not serious about her the first time around (you don’t break up with the love of your life because she is 8 years younger). But because she kind of had a reputation of a loser in the guys department with men breaking up with her they are now trying to make it seem like he was after her all these years when he really wasn’t. Not back then.

    • Betti says:

      I think it was more to do with the fact that the family has the, well deserved, rep as social climbing gold diggers. She only showed an interest in wealthy and well connected men and was such a fame Ho back in the day. Now that any TV/media career is over and she’s calmed down the fame infatuation a bit she’s a much more appealing catch for him.

      But yes this is PR spin to cover the fact that she’s not only settled but is now marrying her best friends man, regardless of they were involved before. I wonder if the friend is thinking of going to the press, hence the stalker love story.

  22. Cara says:


  23. Bridget says:

    Whoever is leaking this stuff needs to STOP. It’s not making anyone look good. And the list of presents? Extra tacky. Pippa seemed like the only Middleton to realize that she’d overplayed her media game and took a step back, hopefully she’s not getting hypnotized by the flashbulbs again.

    • LAK says:

      That would be the Middletons.

      They were similarly OTT about Kate’s engagement.

      • Bridget says:

        I was more wondering specifically which Middleton. Because they need to have their phone confiscated as the clearly have no clue how to make anyone look good.

      • LAK says:

        Got you now.

        Amazingly, for the past decade, the Middletons have been advised on their media strategy by the Sunday Editor of the DM. Before that he was the editor of Tatler magazine, and during his tenure, the Middletons were sold in the same way.

  24. Apples says:

    I can’t believe so many of you here are saying that she has settled because he is “not good-looking”. So that’s a priority when choosing someone to build a life together? Wow :) )) And this coming from the same ladies who claim Pippa is shallow, hahaha! :)

  25. lily says:

    So he’s the male Waity.

  26. Twinkle says:

    At least be obsessed with someone attractive. Jeesh!

  27. birdy says:

    My guess – 2012 she wasn’t willing to even consider a future with a bloke with no title and she thought she was going to be the British Martha Stewart with a lifestyle range of Pippa tips books and paid appearances so she did not want to settle. She was going for the brass ring. Hey, it worked for her sister. Now that reality has kicked in and she has probably spent most of the income she made off the back of the royal wedding, she is willing to settle for financial and lifestyle security. I mean, do you really think she would ever lower herself and the family name to getting a 9 to 5 job like everyone else – especially with Carole’s delusions of pedigree? Pippa must know that her work options are limited by lack of actual talent and reduced opportunity or media interest in her leading to less opportunity to make her own cash therefore she has moved at lightning speed to bag him. Any now they are trying to re-write history as if this guy has been pining for her for the last 10 years.

    This story screams Middleton family plant. The guy doesn’t seem to be the type to want or encourage this level of media coverage of his life. At least, I’d never heard of him before they got together yet all the stories and details of when / how he intended to propose got out before it occurred etc. I fail to believe anything in that article about what he was buying her cause that makes both of them look bad and that this is simply transactional.

    I’m sure that she is a nice enough girl but I would love to see the fall-out of him cancelling the wedding. Carole would go ballistic and that would be fun to watch.

    • Maria says:

      I agree. And if she had wanted a title she could have gone for George Percy, the son of an earl or something. Apparently the chemistry wasn’t there. Nice looking guy, her age. James looks a decent guy and is successful. I wish them both the best.

  28. Zaub says:

    Hello everyone. My first post here on Celebitchy, though I have visited for a while now.

    Speaking of opportunities and lifestyle brands, I have to admit that I recently purchased Pippa’s book, Celebrate, and I am floored that I actually liked it! Pictures are pretty, I am loving the organization by season and dare I say it, some useful tips so far, not to mention the fact that in the foreword, she wholeheartedly admits that her sister’s wedding and her backside are why she’s famous and how she got the opportunity in the first place, lolol.

    I am just really surprised. Her big mistake? Condescending writing, which only like, Martha Stewart or Julia Child could get away with. Because no matter what, your stuff is never going to turn out as perfect as theirs.

    Anyway, I think that she should take some of that Terribly Rich money and create a real lifestyle empire!

    • CharlotteCharlotte says:

      Welcome! I’m a sucker for pretty pictures of food and table settings, so will definitely check out Pippa’s book if I ever find it in a charity store.

  29. Kate Bush says:

    I do t really like Puppa but she looks good in these pics. Not as orange as usual. She’s happy and I say good on her like her ring too it’s not that big!! I wish the Daiky Mail would stop saying she’s flashing it every time she goes anywhere with it.. What is she supposed to do hide it?

  30. Starlight says:

    Do the Middleton girls actually have any female friends, Pippa is pap snapped either walking out with boyfriends, James s dog, ruining ski walking with James Mathews or climbing a mountain with her brother or ski walking with her brother., Wimbledon with her sister or out shopping with her mother. Normally girls get pap snapped having coffee with their girlfriends or partying holidaying with female mates. Just noting Cressida Bonas or Chelsey Davey they seem to have a big girl social group of mates. Kate and Pippa always seemed to be snapped around their bloke, brother, dog or mother.