Royals Pippa Middleton and James Matthews' Relationship Timeline Pippa Middleton and James Matthews have been married since 2017 By Jessica Sager Jessica Sager Contributor, PEOPLE People Editorial Guidelines Updated on July 27, 2022 01:38 PM Share Tweet Pin Email Trending Videos Photo: Max Mumby/Indigo/Getty Pippa Middleton became a household name when she served as the maid of honor at her big sister Kate Middleton's royal wedding to Prince William in April 2011. Six years later, it was Middleton's turn to be a bride when she married Eton-educated hedge fund manager James Matthews. Middleton and Matthews were first linked in 2012 when they were spotted holding hands, though Middleton went on to date Nico Jackson for three years shortly after their initial sighting. Once she and Jackson parted ways, however, Middleton was spotted again with Matthews in December 2015, and the pair have been together ever since. From their fairytale wedding to the birth of their children, here is a complete timeline of Pippa Middleton and James Matthews' relationship. October 30, 2012: Pippa Middleton is spotted with James Matthews Neil Mockford/GC Images Middleton and Matthews were first linked in the fall of 2012, when cameras snapped the pair dining out. Middleton, sporting a black dress with a black-and-white floral jacket, black tights and black heels with a matching clutch, joined Matthews at the trendy London eatery Hakkasan. June 2014: Pippa Middleton and James Matthews bike ride across America Though Middleton began dating investment banker Nico Jackson shortly after she was first spotted with Matthews, the pair remained friends. In June 2014, Middleton and Matthews — along with Middleton's brother James and a team of cyclists — embarked on a 3,000 mile bike ride across 12 American states for the Race Across America charity event. August 2015: James Matthews joins Pippa Middleton's family on a St. Barts vacation Matthews accompanied Middleton, her brother James and her parents Carole and Michael on a vacation to St. Barts during the summer. Middleton was seen being playfully thrown into the water by James and Matthews, though their relationship was still platonic during the trip as she was still dating Jackson at the time. September 7, 2015: Pippa Middleton and James Matthews compete in a charity race Matthews was with Middleton and James for the Otillo Swim Run Championship in Sweden on Sept. 7, 2015. The team ran, swam, jumped and navigated tough terrain in cold, windy weather to raise money for the Michael Matthews Foundation, which was founded to honor Matthews' late brother who died on a mountain climbing expedition. December 2015: James Matthews joins Pippa Middleton's family for another trip to St. Barts Bertrand Rindoff Petroff/Pierre Suu/Getty In December 2015, Matthews joined Middleton, her mother and Prince William for a holiday concert benefiting the Henry van Strabenzee Memorial Fund. Shortly after, Matthews and Middleton headed to St. Barts again to ring in the new year with her brother James. January 2016: Pippa Middleton and James Matthews are officially back on Middleton and Matthews were photographed during a night out together, and PEOPLE confirmed that the couple had rekindled their relationship. July 17, 2016: Pippa Middleton and James Matthews announce their engagement Middleton and Matthews announced their engagement on July 17, 2016, after Matthews reportedly popped the question while the two were visiting northwest England's Lake District. The news was said to be a happy surprise not just for Middleton, but also for the couple's family and friends. Sources told PEOPLE that Middleton's family was fond of Matthews and that he and Middleton seemed very happy and "well-suited" for each other. "The Duke and Duchess of Cambridge are absolutely delighted with the news," a rep for Kensington Palace told PEOPLE. Meanwhile, Middleton's father, Michael, said in a statement, "They make a wonderful couple and we wish them every happiness together." Speculation first arose that Matthews may have proposed after Middleton was spotted at several events keeping her left hand out of the sight of photographers. However, the day their engagement was officially announced, Middleton posed for photos outside of her home with her new diamond ring on full display. July 20, 2016: Pippa Middleton shows off her engagement ring Ricky Vigil M/GC Images Middleton showed off her new diamond ring while walking in London. David Christopher Allen of 77 Diamonds told PEOPLE, "It is an Asscher-cut diamond, and in order to get a beautiful cut, the diamond needs to be of top clarity. If it is a flawless stone then it could be 200,000 pounds (about $263,000)." July 31, 2016: Pippa Middleton honors James Matthews' late brother Weeks after her engagement, Middleton climbed the Matterhorn in Switzerland to honor Matthews' late brother, Michael, who died while climbing Mt. Everest in 1999. Middleton's brother joined her on the trek. She said in a statement, "It was humbling to have been able to climb one of the world's most beautiful mountains and raise money for a charity created in memory of an extraordinary young man who lost his life on another peak. Although I have raised money in the past for the Michael Matthews Foundation, it has now become even more important to me and my family." She added, "Although neither I nor my brother ever met Michael, we both share his spirit and passion for the mountains. We made this climb knowing he would have been there nudging us on, and we are honored to be supporting his memory." Middleton also explained why her fiancé wasn't with her for the climb. "It would have been good if James Matthews had been here to share the experience, something I know he would have loved to have done," she said. "Mountain climbing, though, has disturbing memories and, understandably, James kept his feet firmly on the ground, whilst giving us his complete support." September 2016: Pippa Middleton opens up about how she and James Matthews cope with the spotlight In an interview with the Daily Mail published on Sept. 18, 2016, Middleton confessed that coping with fame had, at times, been tricky for her and Matthews. "There's always something cropping up and that has to be managed on my own. It's been a real eye-opener for James. There have been quite a few hurdles to negotiate," she said. Promoting her cookbook, Heartfelt, she noted that there was one specific dish that was close to her and Matthews' hearts: halibut with roasted tomatoes and herb dressing. "I am sure he might choose a different dish as his favorite, but it was a very special dinner for us," she said. "You roast the halibut and serve it with lentils. It's delicious. James loves it." She also said that she and Matthews' shared love of the outdoors is part of their relationship's glue. "I think James and I have the same spirit. We are both competitive. We have had many adventures together," she said, adding jokingly, "I don't think it would work with a couch potato … I think we do exhaust most people." October 27, 2016: Pippa Middleton plans her wedding to James Matthews A friend of Middleton told PEOPLE that the Celebrate author was already planning her big day, choosing a May 2017 date. "Of course, she is super excited and already planning everything," Middleton's pal said, adding that Middleton and Matthews "have a lot in common — he's charming and old-fashioned. Everyone thinks he's quite the catch." December 9, 2016: Friends of Pippa Middleton say she wants a low-key wedding — and marriage Friends of the world's most famous bridesmaid told PEOPLE that Middleton's dream wedding was pretty much the opposite of the spectacle that was the royal wedding. One insider said that Middleton and Matthews both had a "deep desire" to live their lives out of the limelight, while another noted that the couple particularly looked forward to "having children and leading a quiet life." May 20, 2017: Pippa Middleton and James Matthews get married James Matthews and Pippa Middleton. Arthur Edwards - WPA Pool/Getty Middleton and Matthews tied the knot at St. Mark's Church in Englefield, England. Middleton wore a custom cap-sleeved gown by Giles Deacon for her big day as well as Manolo Blahnik pumps, a tulle veil by Stephen Jones, the same earrings she wore to big sister Kate's wedding and a Maidenhair Fern tiara with a matching hairpiece by Robinson Pelham. Kate helped her younger sister with her gown as she walked down the aisle, escorted by their father, Michael. Prince William and Prince Harry were in attendance, as were Middleton's niece and nephew, Princess Charlotte and Prince George. Matthews' younger brother, reality star Spencer Matthews, was also in tow, along with Countess Philippa Hoyos, Lily French, Avia Horner, Casmir Tatos, Edward Sebire and William Ward. "This is the wedding Pippa and James dreamed of," a source close to the happy couple told PEOPLE. "They said all along they wanted it to be a private family wedding at home in the beautiful countryside with their closest friends and family." May 21, 2017: Pippa Middleton's uncle says she and James Matthews were attentive to all of their wedding guests Neil Mockford/GC Images A consummate hostess! Middleton's uncle, Gary Goldsmith, reshared a photo on Twitter of the vintage convertible Matthews drove from the wedding ceremony to the reception. The proud uncle captioned the snap, "Brilliant couple who gave everyone time and attention – this is the 1st ever E-Type ever made btw." The wedding reception featured everything from an aerial performance to a Beatles singalong, all hosted at a glass palace at the Middletons' 18-acre estate in Bucklebury, England. May 23, 2017: Pippa Middleton and James Matthews jet off to their honeymoon Following their nuptials, Middleton and Matthews took off for their honeymoon in French Polynesia. The couple were spotted touching down at Los Angeles International Airport on their way to their island getaway. May 25, 2017: Pippa Middleton earns a new title Marrying Matthews earned Middleton a new title: the future Lady of Glen Affric. Matthews is set to inherit the title of Laird of Glen Affric from his father, David. Until that happens, the couple can call themselves "Mr. and Mrs. Matthews of Glen Affric" if they so choose. May 31, 2017: Pippa Middleton and James Matthews continue their honeymoon in Australia Middleton and Matthews continued their post-wedding celebrations with a trip to Australia. The pair was photographed holding hands as they boarded a seaplane in Sydney, where they dined at the Cottage Point Inn. The couple stayed at the Park Hyatt hotel in the city, which has a view of the iconic Sydney Opera House, and climbed the Sydney Harbour Bridge during their trip. June 11, 2017: Pippa Middleton and James Matthews attend a wedding in Sweden The newlyweds attended the wedding of friends Jöns Bartholdson and Anna Ridderstad in Stockholm on June 11, 2017. Middleton wore a long-sleeved white floral print dress with black trim, while Matthews opted for a full tuxedo with tails, a white cummerbund and bow tie. Stockholm was reportedly the last location on their three-week honeymoon. July 2, 2017: Pippa Middleton and James Matthews attend another wedding in Ireland Middleton and Matthews attended yet another wedding in July 2017, this time in Ireland for her longtime close friend Camilla Campion-Awwad. Middleton wore a green A-line knee-length dress with a single red flower design from Alice Archer, accessorizing with a black-and-gray fascinator, gray pointy-toe pumps and a small gray clutch. July 14, 2017: Pippa Middleton and James Matthews watch Wimbledon together Karwai Tang/WireImage Matthews and Middleton took in Wimbledon together for the first time as a married couple on July 14, 2017. The pair sat in Centre Court as they watched Sam Querrey's match against Marin Cilic. May 20, 2018: James Matthews and Pippa Middleton celebrate their first wedding anniversary Max Mumby/Indigo/Getty Middleton and Matthews rang in their first year of wedded bliss on May 20, 2018 — just one day after Prince Harry and Meghan Markle walked down the aisle in their own royal wedding. Middleton and Matthews also attended Meghan and Harry's nuptials, though Meghan wasn't present for their 2017 ceremony, just the reception. June 2018: Pippa Middleton confirms she's pregnant with her first child with James Matthews Six weeks after reports first surfaced that Middleton was pregnant with her first child, she confirmed in a column for Waitrose Kitchen magazine that she and Matthews were expecting their first child together. Middleton also shared that unlike her sister Kate, she did not experience severe pregnancy sickness, or Hyperemesis Gravidarum (HG). "I was lucky to pass the 12-week scan without suffering from morning sickness. That meant I was able to carry on as normal," she wrote. October 12, 2018: Pippa Middleton and James Matthews attend Princess Eugenie's wedding to Jack Brooksbank James Matthews and Pippa Middleton. Max Mumby/Indigo/Getty Matthews and Middleton, then-nine months pregnant, attended Princess Eugenie's royal wedding to Jack Brooksbank. Middleton wore a tea-length emerald-green long-sleeved dress with a matching fascinator and heels to the ceremony. October 15, 2018: Pippa Middleton and James Matthews welcome their first child Middleton and Matthews welcomed their first child, a baby boy, on Oct. 15, 2018. The baby was born at 1:59 p.m. local time and weighed 8 lbs., 9 oz. "Everyone is delighted, and mother and baby are doing well," Middleton's rep told PEOPLE. In a statement, Kensington Palace told the press, "The Duke and Duchess of Cambridge are thrilled for Pippa and James." November 11, 2018: Pippa Middleton and James Matthews' son's name is revealed Middleton and Matthews' revealed their baby boy's name, Arthur Michael William, to the world on Nov. 11, 2018. The name Michael is speculated to be a tribute to James' late brother, Michael, as well as to Middleton's father. December 4, 2018: Pippa Middleton and James Matthews make their first post-baby public appearance Ricky Vigil M/GC Images Matthews and Middleton made their first public appearance since becoming parents on Dec. 4, 2018. Clad in coordinating burgundy (his tie matched her coat), Middleton and Matthews attended the Henry van Straubenzee Memorial Fund Christmas carol concert. May 18, 2019: Pippa Middleton and James Matthews attend a wedding just before their second anniversary Pool/Max Mumby/Getty Just days before their second wedding anniversary, Middleton and Matthews attended the nuptials of Lady Gabriella Windsor and Thomas Kingston. July 12, 2019: James Matthews and Pippa Middleton enjoy a date at Wimbledon Karwai Tang/Getty Tennis fans Middleton and Matthews attended the men's semifinal matches at Wimbledon on July 12, 2019. The couple held hands as they walked the grounds and were seen laughing and chatting in their royal box seats. December 25, 2019: James Matthews joins Carole and Pippa Middleton in St. Barts Skipping the snow and sleds for Christmas, Matthews, Middleton and her mother Carole enjoyed a trip to St. Barts for the holidays. Middleton, wearing a white-and-black polka dot bikini, and Matthews, sporting swim trunks with a landscape design, were photographed on the beach with goggles in hand. Dec. 14, 2020: Pippa Middleton and James Matthews reveal they're expecting their second child On Dec. 14, 2020, reports revealed that Matthews and Middleton were expecting baby number two. A source told Page Six, "Pippa and James are thrilled. It's fantastic news amid a difficult year. The entire family is delighted." March 15, 2021: Pippa Middleton and James Matthews welcome a baby girl Middleton and Matthews welcomed daughter Grace Elizabeth Jane on March 15, 2021. A source told PEOPLE that the little girl was born at 4:22 a.m., weighing 6 lbs., 7 oz. The insider said, "She's perfect. Everyone is overjoyed at such a happy arrival." A rep for Kate Middleton and Prince William told PEOPLE in a statement that they were "overjoyed" at the news of their new niece's birth. May 20, 2021: Pippa Middleton and James Matthews celebrate their fourth wedding anniversary Time flies when you're in love. Middleton and Matthews marked their fourth wedding anniversary on May 20, 2021, two months after welcoming their daughter, Grace. January 14, 2022: Pippa Middleton and James Matthews enjoy a date night PIppa Middleton and James Matthews. Ricky Vigil M/GC Images Though Middleton and Matthews largely flew under the radar after welcoming their son and daughter, they enjoyed a rare date night out together on Jan. 14, 2022. The couple attended the Cirque du Soleil's Luzia show at the Royal Albert Hall in London. June 5, 2022: Pippa Middleton and James Matthews are expecting their third child Multiple sources confirmed to PEOPLE that Middleton and Matthews were expecting their third child together in June 2022. The mom of two displayed a growing baby bump while attending the "Party at the Palace" concert outside of Buckingham palace to celebrate Queen Elizabeth's 70-year reign. July 11, 2022: PEOPLE confirms that Pippa Middleton and James Matthews welcomed their third child One month after the couple's third pregnancy was announced, PEOPLE confirmed that Middleton and Matthews had welcomed a baby girl in June. July 26, 2022: Pippa Middleton and James Matthews reveal the name of their third child In late July 2022, PEOPLE learned that the couple named their baby daughter Rose, which is the birth month flower for June.