Pippa Middleton is reportedly getting a marriage proposal… in September?

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Last fall, Pippa Middleton and Nico Jackson finally ended their relationship after months of drama. He basically moved to Switzerland to get away from Pippa, but that still didn’t end the relationship. The relationship only ended when Pippa was seen having a “sleepover” at James Matthews’ house. Suddenly, Pippa and Nico were done and then Pippa and James Matthews were a thing. Their relationship was confirmed just days into the new year, with sources dishing that Pippa’s new boyfriend is “terribly rich” and very much into Pippa. And in 2016, we really haven’t seen that much of Pippa, lending credence to the idea that Prince William convinced Pippa to give up Pippa-Tipping and “writing” so she could focus on landing a husband who would financially support her. And now it might be happening! Per the Daily Mail’s “Diary” gossip girl:

I’m loathe to spoil a surprise, but is Pippa Middleton’s boyfriend about to propose? Sources tell me that James Matthews is whisking her away to the Caribbean island of St Barts in September – where he might pop the question at his parents’ exclusive hotel, Eden Rock.

A ‘save the date card’ is already circulating among close pals with the message: ‘Don’t Tell Pippa,’ while mum Carole is in on it, too. As Pippa’s brother James is now back with Donna Air, could it be a race to see who walks down the aisle first?

[From The Daily Mail]

To be fair, there were tons of these kinds of rumors about Pippa and Nico and her boyfriend before Nico too. It’s “the Middleton way” to publicly encourage Pippa’s boyfriends to propose by dropping hints to gossip columnists. The Middleton family did it with Kate and Prince William too, during The Waity Years. That being said, I do think Pippa has found The One. If we’re defining The One as “some guy who is terribly rich and well-connected.” Which is all she’s ever wanted! I’m hoping he does propose just so Pippa can change her storyline, you know?

Photos courtesy of Getty, WENN.

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79 Responses to “Pippa Middleton is reportedly getting a marriage proposal… in September?”

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  1. lilacflowers says:

    Why wait until September? Is that the harvest season for oranges?

  2. mytake says:

    That would be interesting. James Matthews’ brother, Spencer, is a reality show “star” in the UK.

    • Talie says:

      I heard he declined to another season of that show…a lot of people think his family put him on ice because of they want this marriage to go through.

      • hmmm says:

        Hmm. So is Pippa loved for herself or her connections? That would be irony. Not like any of the Midds care how it happens as long as there are lots of perks and a lot of filthy lucre.

  3. Sayrah says:

    So orange… I’m just here waiting for the GoT post

  4. Size Does Matter says:

    Shhhhhhhhh! It’s still top secret you guys!

  5. Maum says:

    She looks so pretty on that last picture.

    Probaby because the over exposure makes her look normal coloured.

  6. Sixer says:

    Haha. Circulating a card that says ‘don’t tell Pippa’ while providing details of said card to gossip outlets. Good lord. It’s all machinations with everyone in the public eye, isn’t it? Can’t these people ever just be NORMAL?

  7. juice says:

    why are we still talking about this chick?

    • Citresse says:

      Good question. She’s equally if not more vapid than her sister. The only pertinent question regarding Pippa is who’s oranger (next appearance) Pippa or Trump?

      • Lisa says:

        Not that I’m a fan or anything but in Pippa’s defense, she does more for charity than that vapid, lazy sister of hers ever has. Sure, she’s a Wisteria Sister but she’s not just shopping and waiting by the phone like Kate was. Carole must be salivating at Pippa possibly marrying into a family with their own resort in the Caribbean!

      • Citresse says:

        Yes Lisa, good point, however the real test is the behaviour long haul. Kate also did a few appearances for charity prior to her marriage to William though hers always had an ulterior motive where William was concerned. Can we really say it was and is different for Pippa with regard to marriage? I admit, Pippa did more strenuous, more physically challenging events but what was her number one intention?

      • hmmm says:

        I wouldn’t say Pippa laboured hard for these charities. Sports runs keep her fit, and galas keep her name in the public eye. That’s about it. A Wisteria has to give fragrant lip service to the status quo in order to climb.

      • Bridget says:

        The stuff that Pippa’s doing goes way beyond ‘keeping fit’. Credit where credit’s due: the events that she does in conjunction with her charity require a lot of training and dedication. She’s not exactly doing a local 5k.

      • HH says:

        @Citresse – Agreeing with Bridget here. The charity events that Pippa has done go WAY beyond keeping fit. These are endurance events: marathons and triathlons. Furthermore, she has been doing them for a LONG time. I don’t think this is about marriage prospects, specifically. I think part of the reason is to keep up a socialite status and increase the name brand. So, some of it is self-serving. But, the type of charity sporting events that she does aren’t the things that one takes part in lightly. She could find a TON of other events to do that would require less work. Kate also did charity events pre-marriage, but it mirrored what she does now: dinners and galas.

      • hmmm says:

        So she does endurance marathons. An achievement for her. Keeps her very fit. She tacks on the charity. It seems the grandness of her events are conflated with a grand charitableness. Not buying it.

      • HH says:

        @hmmm – I don’t think anyone is “conflating the grandness of her events with a grand charitableness.” However, people are brushing her charity activities aside as though they take minimal effort on her part and/or are *entirely* self-serving. As I stated, I most certainly believe there are self-serving reasons as to why she does these events. That’s almost inarguable. However, if this was all about image, Pippa could take a MUCH easier route. The credit being given here is that Pippa is not simply cutting ribbons and going to dinners, she is putting in work.

      • notasugarhere says:

        Other routes wouldn’t enable pap photos of her running around London in her expensive new running gear or being photographed in the same skiing events as Scandinavian royals.

        She was rumored to be trying to become a lifestyle, nutrition, and health guru. Participating in these types of charity events are self-promoting for that.

      • Bridget says:

        Pippa has chosen events that are no joke. The Lewa Marathon, the Great Wall marathon, the duathlon in Norway (I think), are pretty intense physical challenges, and she performs them well, showing far more commitment than just wanting to be seen in her running gear (and as a runner who is frequently on busy streets in my city in my damn cute running gear, I take that crack kind of personally). At this point she’s been doing this for years and seems to be taking her commitment seriously. And going to have to point out, she isn’t required to do this. She isn’t a public servant.

      • notasugarhere says:

        She isn’t a public servant. She’s also part of (almost) the only royal in-law family that craves and seeks public attention. None of these career goals and public endurance events were undertaken prior to her sister finally getting the ring. Telling.

  8. Vivi says:

    I think it’s sad that this is what this woman has been reduced to. All the pressure put on her to stop being herself, stop wanting to find her own path and just marry rich and sit down.
    She shouldn’t be defined by who she marries or by the fact that she hasn’t managed to nab a husband. That’s archaic thinking.
    But maybe I should just go back and rewatch Downton Abbey to understand how British high society works.

    • GoodNamesAllTaken says:

      She’s old enough to change that if she wants to, and I think she tried with her phenomal flop entertaining book, and then with several attempts at writing and TV jobs. Unfortunately, she’s not very bright or talented. She’s still talking about the fuss over her bottom at Kate’s wedding while everyone else moved on two weeks later. I don’t see her as some victim with no choice in the matter.

      • Vivi says:

        But she’s tried though hasn’t she?
        Yes she’s capitalizing on her sister’s name but why wouldn’t you?
        And she’s doing it in order to try and do stuff on her own. Her endevours were embarassing but she still tried. She might not be clever, who knows. But it’s still patronising that everypne is telling her that her greatest success in life would be a successful husband.
        If all she wanted was to marry rich she wouldn’t have sabotaged her previous relationship so publicly.
        This is just what is “expected” of her now.

      • notasugarhere says:

        She didn’t try any of those things until after her sister finally landed the big prize. Little to no work ethic or trying out of Pippa until after the engagement-and-wedding.

        She had a decade to try to build a career while her sister was in waiting mode. What did she do? Pretend to work a bit for the family firm, just like her sister, while spending most of her time as Party Girl About Town Mark 2 supported by her parents.

        To me that indicates she never had the desire to achieve beyond landing herself almost as big a “prize” as William (the Percy heir their PR insists she never looked at as a possible catch).

      • hmmm says:

        And don’t forget lazy, GNAT. Like her pretender sister, she does the bare minimum for the greatest reward.

      • GoodNamesAllTaken says:

        @Vivi
        I slightly misunderstood what you meant. Yes, it’s gross that in our society, certain women are targeted for this “failure to catch a husband” story, and that she is basically being told that nothing else matters in people’s opinion of her.

    • notasugarhere says:

      Her sister’s goal was wait for a decade for him to finally give in, then marry rich & famous and refuse to work.

      Why assume Pippa’s self-chosen game plan is any different? Remember, she’s the other half of the Wisteria Sisters.

    • Lisa says:

      I agree with you, Vivi but remember who her mother is. The scheming manipulative Carole Middleton has made it her life’s work to reach the upper echelons of British society at any cost including pimping out her own daughters to do it. Why do you think every one of her kids is so emotionally stunted? They’ve all been trained by Mummy to tow the family line at the expense of their own well-beings. It seems like their entire lives have been planned out by Carole and none of them seem strong enough or smart enought to stand up to her and break away from her and her schemes. Such a dysfunctional family!

      • Billie says:

        Do you hear the way you sound? This is not a normal way to talk about other human beings. Yikes.

    • Boo says:

      I agree Vivi. It’s very sad the way these girls have been raised. It’s difficult to blame them because we are a product of our environment and in the absence of serious harm or threats in that environment, how does a child know to be different than what their parents are teaching?

      Plus, as you said, it’s british society. This IS exactly how most are raised or used to be. I hope it’s becoming more different.

      Also I have a problem criticizing people for not being bright or intellectual. Pippa works hard at her charity endeavours – that is serious dedication. Whatever her reasons, she does it and takes on laborious work. That’s worth as much, sometimes more, than being an intellectual showing up to give a speech.

      This man seems to love her. I hope they’re happy together. I’ve been worried her life path will mirror poor Princess Margaret’s. That was tragic. Nobody in this day and age should suffer the same fate due to who her sister or brother married.

  9. what's inside says:

    September? Plan a winter wedding?

  10. LAK says:

    It’s so sad that in 2016, the definition of a woman’s success is still landing a rich husband who can keep her.

    I would really love a similar storyline to centre on a family of brothers, celebrated for the rich wives they set out to acquire, who would keep them.

    Mind you, the VCs are very close, but still…..

    • Red Snapper says:

      The pressure to make a successful marriage, where success is defined as a rich and well connected husband, isn’t coming from outside the Middleton bubble. You think Carole would be okay with Pippa coming home with a plumber or a bus driver?

      • notasugarhere says:

        +1

        Have we ever know Pippa to have a romantic interest who wasn’t either titled or wealthy?

      • LAK says:

        Red Snapper: I know. Le sigh. Yet it seems that the world has accepted this storyline for Pippa as if she was no other options.

        Considering she’s tried her hand at working even though that was disastrous, she chucked it in and is settling for the rich and well-connected husband route to riches.

        I always wonder if she would have followed that path if her work efforts had been a success.

        I’ll add a caveat that she was always going to date/marry rich and well-connected, but it’s sad to see that her in her storyline, failing to land a rich, well-connected partner is deemed a bigger failure than her being unable to support herself.

    • Div says:

      Yep. I side-eye Pippa but at least she seems to kind of have her own thing going on from running marathons to doing charity events compared to her siblings. I also think she “actually” worked for her parent’s business, unlike her brother and Kate who basically showed up once a week. Her Pippa-tips were embarrassing and ridiculous but she does seem to have her own life and while I bet she wants an rich man…I don’t think that’s the “only” thing she wants or focuses on. It just seems a bit like the Cambridge PR firm…to sh*t on her to make Kate look a bit better.

    • notasugarhere says:

      Even sadder that three generations of women in this family have chosen to define themselves by “marrying up”.

      • LAK says:

        Where can Charlotte go?

        A crown prince of another country perhaps?

        Since all the Crown Princes in the younger generation are female, barring PGTIPS and Christian of Denmark, is Christian her only option if she follows the family pattern?

      • notasugarhere says:

        Who knows, that might please CP Mary to no end. The IHA would never approve a Brit as the wife of Hisahito.

      • Megan says:

        Why are we assuming Charlotte will want to marry? And why are we assuming she will want to marry a man?

      • notasugarhere says:

        I think we were making a general point about Middleton’s marrying up and royal alliances, but I agree with you about both points Megan.

      • LAK says:

        Megan: The Middletons have shown that marriage to a rich, well-connected person is their preferred route to riches.

        Even if Charlotte is gay/trans she’ll be indoctrinated to pursue UP, socially speaking. I doubt very much that she’ll be allowed to opt out entirely.

        James may be low key as far as his girlfriend, but people forget that her babyfather is very deeply connected to all the Rothschilds and Goldsmiths (Jimmy, not Carole) and their world. Therefore on the surface she may not bring lots of cash to the table, but she brinfs lots of connections.

      • Roslyn says:

        LAK: How for UP can the daughter of a king/future king go? It is my hope that Charlotte is a tomboy and becomes a mechanic or pilot or physicist and refuses to play the marriage game her mother’s family want her to engage in. I would love her to become a real rebel, and to marry someone of like mind with whom she is genuinely happy, whoever he/she might be.

        I hope the same for Pippa. I like Pippa. If the bloke is going to ask her to marry him, why not just do it? Why wait until September?

  11. Loula says:

    Nice of her to help the British Heart Foundation by matching her skin to their logo.

  12. Rae says:

    I root for her, simply because unlike Waity, she is doing her own thing quite well (have you seen some of the physical endurance events she has taken part in? Many would struggle!)

    I also think that she is not as free to choose as she wants, considering she is sister to the future queen (shudder), and has a seemingly very controlling mother.

    However, my most important comment I want to make on this post is simply that I really want to pass her some aftersun lotion.

    Her skin looks sore on the original photos. Ouch.

    • CuriousCole says:

      +1. I am puzzled why Pippa’s beauty ideal appears to be an oompa-loompa. But I definitely admire her consistent commitment to charity endurance events. I think it takes courage trying to do your own thing despite constant media judgement and controlling relatives.

      Carole reminds me of Empress Maria Theresa, scheming to increase her power by marrying off her children to the highest titles in Europe, no matter what. (Her youngest daughter became Queen Marie Antoinette of France, and we know how well that ended. Shades of clueless Kate?)

  13. Bess says:

    Carol Middleton is a self-made woman. Why is it that her only goal for her own children to marry someone rich and well-connected? It doesn’t make sense to me.

    • paddyjr says:

      That’s always bothered me as well. Both parents worked hard to create a successful company, yet not one of their three children has any ambition, nor have they been encouraged, to do anything other than be the idle rich

    • hmmm says:

      I question how “self-made” Carol Middleton is. She started out with Michael’s substantial inheritance and tons of Uncle Gary’s shady money. To this day, the business accounts are shrouded in secrecy. She use other people’s money to get to where she is.

      Carole Middleton is a master manipulator, high on the Machiavellian scale, and the first thing she did, having been raised in a council flat, is marry up.

      • Tourmaline says:

        Yes to this. There is something shady going down there. Also, I can’t see how Party Pieces is thriving to the degree that the Middletons can all live lives of luxury without any noticeable uptick in their entrepreneurship.

        If you want to see something alarming check out Uncle Gary’s twitter–he tweets constantly. Uncle Gary is overjoyed about Brexit.

    • notasugarhere says:

      Their net worth has been greatly exaggerated. The inheritance wouldn’t have gotten them this far, plus all the kids schooling, and PP doesn’t bring in what some fans think. How much of their funding comes from Uncle Gary?

      See the Telegraph article
      Royal Wedding: Middletons’ money – how was it made?
      The firm Party Pieces is credited with making the family fortune. Andrew Gilligan examines the figures

    • Megan says:

      Carole wants her children to marry into society. While I think she expected them to work, she allowed her children to prioritize marriage over career.

  14. CoKatie says:

    Just personally speaking, I have zero idea why you would even want to have a rumor like this out there. What if the guy has no intention of proposing? How embarrassing is that return flight going to be?

    • GoodNamesAllTaken says:

      Agree. And I wouldn’t want to marry someone who married me because I pressured or tricked him.

      • Egla says:

        You have no idea what some people can and will do to have what they want. I have seen first hand some things (even “suffered” some). You would be amazed. A girl I know put a fake ring on her finger at work so everybody started making assumption about a guy she liked. I – on purpose I might add- went to congratulate him. He protested but today they are married with a child. She didn’t back, didn’t surrender and was not ashamed. Oh and now she is rewriting history making it sound like they were madly in love and always out in the open together which it’s not the case. And she has more money than him.
        Pipa WILL land a rich guy no matter what, better sooner then latter.

  15. Sharon Lea says:

    They say Camilla put her engagement announcement to Andrew Parker Bowles in the paper, (before he actually proposed!) he saw it and realized he couldn’t really ‘back out.’ Camilla, now there is a woman with a play book.

    • als says:

      With all due respect, if you are that idiot to fall for that trick, you deserve whatever is coming your way and I imagine it’s nothing good. It wasn’t good for Mr. Bowles.

      • Sharon Lea says:

        Ha, well maybe Andrew got her back at her own game, because the rumors are that he always had side pieces which is why she had time on her hands and reason to pursue Charles to try to make Andrew jealous.

    • spidey says:

      Who is “they”

  16. Iknowwhatboyslike says:

    I feel like I’m in an 18th century drawing room.

  17. Megan says:

    I was at Eden Rock a few years ago. If it as exclusive as the British press makes out, how was an ordinary slob like me able to book a stay online?

  18. Nancy says:

    Looks like she rolled in Trump’s body lotion. Not a good look……on either of them. These people have the money, what in the world are they using and why doesn’t someone tell them they put Orange Crush to shame.

    • GoodNamesAllTaken says:

      I don’t get it, either. There are lots of self tanners that don’t make you orange.

  19. abby says:

    CAN SOMEONE HELP THE MIDDLETON GIRLS WITH THEIR MAKEUP?

  20. Pmnichols says:

    Step aaaaway from the self tanner girl. Good grief.

  21. Leah says:

    No one should be the color of radioactive beef jerky.

  22. Tourmaline says:

    “Don’t Tell Pippa” that sounds like a great surprise proposal strategy there!

    I see Pipps was at Wimbleton today but it looks like she was with her brother. Maybe James Matthews and Donna Air both had to work today haha