5:35pm PDT, May 25, 2021
Wonderwall.com is taking a look back at the celebrities who found love, suffered heartbreak or experienced some other major event in their love lives in May 2021, starting with this back-on power couple… In late April and early May, multiple media outlets reported that Jennifer Lopez and Ben Affleck were spending time together again but keeping things platonic in the wake of her April split from Alex Rodriguez. Then on May 8, the duo were snapped driving in an SUV while visiting a luxury ski resort in Montana for a week-long romantic getaway. Later that day, they were photographed purportedly holding hands as they deplaned from a private jet in Los Angeles before sharing a ride back to her L.A. home. (See photos here.) According to multiple media outlets, the erstwhile Bennifer kept in touch following their 2004 split but truly reconnected after he “started flooding her with emails” while she was shooting the upcoming action flick “Shotgun Wedding” in the Dominican Republic earlier this year. (According to TMZ, they started communicating after A-Rod was first accused of cheating on J.Lo with “Southern Charm” star Madison LeCroy but didn’t start hanging out again until after the former professional baseball player — who was still hoping for a reconciliation — was fully out of the picture.) By the end of the month, it was clear that Bennifer was officially back on: According to an Us Weekly source, “the attraction is hot” between the pair, who are “making up for lost time.” On May 23, they were photographed spending time together in Miami, where she’s been working on various projects. In other words, they’ve now been seen together in three states in as many weeks!
Now keep reading for more celeb love life updates for May 2021…
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In mid-May, Travis Barker’s ex-wife, Shanna Moakler, alleged that the blink-182 drummer had affairs with Kim Kardashian and Paris Hilton during their tumultuous marriage. According to multiple Page Six sources, however, Travis — who previously fessed up to having a crush on Kim early in their friendship and has been dating her older sister, Kourtney Kardashian, since early 2021 — “never had a romantic relationship” with Kim and “has been in love with Kourtney for forever.” Shanna actually spent most of the month running her mouth about Travis and Kourtney: During an interview with People magazine, she insisted that although she’s “very much over” the rocker, has “no ill will” toward him or his new love and is “genuinely happy” for them, she thinks “some of the PDA that he’s doing with her is weird.” She added that her social media posts with boyfriend Matthew Rondeau spoofing Kourtney and Travis were not meant as an “attack” on the couple — but rather an attempt to rile up her fans — and that she and the male model are still going strong after briefly pressing pause on their relationship earlier this year. Meanwhile, Kourtney reportedly has “a tense relationship right now” with her former long-term partner, Scott Disick, who’s struggling with the fact that she’s “in love with someone else” and is “really distancing himself” from her. An “Entertainment Tonight” source explained that Scott “has come to terms with the fact that Kourtney and Travis are serious and has accepted it,” although “he previously had high hopes that Kourtney and him might get back together one day.” Still, he and his new girlfriend, Amelia Gray Hamlin, are “doing well.” (The 37-year-old father of three is the teen model’s “first serious boyfriend” and “she’s really into him.”) Amid all the drama with their exes, “Entertainment Tonight” reported that Kourtney and Travis have discussed “getting engaged and married one day.” According to a source, Travis “would absolutely love to tie the knot with Kourtney” — he called her the love of his life in the comments section of a May 20 Instagram post! — but she “doesn’t feel the need or want the pressure of getting married” just yet, though a second source noted that she “can see a forever with Travis.”
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In early May — after Kylie Jenner and Travis Scott sparked questions about the nature of their relationship with their flirty behavior while celebrating his birthday in Miami — “Entertainment Tonight” reported that, according to a source, the former couple are “exploring their relationship romantically again.” Then on May 21, TMZ reported that, according to multiple sources, they’re actually in an open relationship: They’re back together but aren’t exclusive and have both signed off on the arrangement. After the TMZ report hit the Internet, however, Kylie took to Twitter to shoot it down, tweeting that it’s “careless and disrespectful to throw this narrative out there without knowing what’s true.” She did not, however, deny that she and Travis are an item again.
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On May 9, Porsha Williams sparked questions about the nature of her relationship with Simon Guobadia — the estranged husband of “The Real Housewives of Atlanta” newbie Falynn Guobadia — when she took to Instagram to share a slideshow of photos of herself celebrating Mother’s Day with him (and her ex-fiancé, Dennis McKinley!) as she rocked what appeared to be a massive engagement ring. Her ex — with whom she shares daughter Pilar Jhena — further fueled engagement rumors when he wrote in the comments section, “Congrats P! Cheers to your next chapter!” The following day, Porsha confirmed on “Dish Nation” that she’s “happy” and “in love” with Simon. She then wrote on Instagram that her relationship with Simon “began a month ago,” that he filed for divorce from Falynn in January, that she “had nothing to do with their divorce” and that she and Falynn “are not friends.” Simon, meanwhile, confirmed they’re engaged in the caption of a slideshow of photos with Porsha on Instagram, writing, “I asked her to marry me because we checked ALL of each other’s boxes, and then some.” In the wake of the news, Falynn released a statement saying she was “focusing on finalizing my divorce and healing.” (Curiously, Falynn said back in March that she and Porsha “clicked” after they met through Simon and Dennis, who run in the same social circles.)
On May 13, People magazine broke the news that John Mulaney and Olivia Munn — who gushed back in 2015 that she was “so obsessed” with the comedian — are dating amid his split from his wife of six years, Anna Marie Tendler. “This is very new, they’re taking it slowly,” said a source, noting that the new couple “met at church in Los Angeles.” Just three days earlier, Page Six broke the news that John asked his artist wife for a divorce about three months ago — around the time he completed a 60-day stint at a Pennsylvania rehab center, where he sought treatment for alcohol and cocaine addiction. His rep confirmed the breakup news, which Anna Marie also addressed in a statement to the New York Post’s gossip column: “I am heartbroken that John has decided to end our marriage. I wish him support and success as he continues his recovery,” she said.
On May 11, People magazine broke the news that Armie Hammer is dating a local dental hygienist in the Cayman Islands, where he’s been living in the wake of a sexual abuse scandal. Two days later, DailyMail.com identified his new real-life leading lady as Lisa Perejma. According to a source, he’s “happier and healthier” than he’s seemed “in a long time” thanks to the Canadian beauty, who’s “really helped turn [his] life around” and is “so good for him.” The insider went on to say that the only “obstacle” in the new relationship is the embattled actor’s estranged wife, Elizabeth Chambers, who’s “made his life a living hell” amid their breakup. Alleged a Page Six source, “Elizabeth was sending [Lisa] horrible messages from a fake Instagram account. … I was shocked with her behavior.” Earlier this year, it was Elizabeth who was said to be “in shock” over the allegations against her husband.
Kat Dennings took to Instagram on May 13 — just 10 days after she first revealed that she and rocker Andrew W.K. are an item — to announce that they’re engaged.
During an interview with GQ that debuted online on May 19, A$AP Rocky finally confirmed long-standing rumors that he and Rihanna are an item, calling her “the love of my life,” “my lady” and “The One.”
On the May 12 episode of the “Hollywood Raw” podcast, Audrina Patridge finally confirmed longstanding rumors that she once dated Chris Pine. They met when he approached her at an award show in Las Vegas about a decade ago, she revealed, adding that she wasn’t familiar with him at the time. They ended up going out “more than a few times” but ultimately discovered they didn’t have enough in common to make a relationship work. Still, she had nothing but good things to say about the “Star Trek” star, with whom she “kept in touch for a little bit” after they went their separate ways. Audrina also noted on the podcast that she’s currently single and hasn’t dated anyone since she went out with Sean Stewart in late 2020.
Longtime pals John Mayer and Cazzie David — who previously romanced “Saturday Night Live” star Pete Davidson — sparked a fresh round of questions about the nature of their relationship when they stepped out for dinner in the Los Angeles area on May 2. An E! News source, however, insists that despite how things may appear, the chart-topper is single and there’s nothing romantic going on between him and Larry David’s daughter.
It was a big month for Bachelor Nation engagements… On May 11, Kaitlyn Bristowe, who headlined season 11 of “The Bachelorette,” and Jason Tartick — who competed for Becca Kufrin’s heart on season 14 of “The Bachelorette” in 2018 — took to Instagram to announce they’re engaged after more than two years of coupledom. … On May 15, Sarah Herron — who competed for Sean Lowe’s heart on season 17 of “The Bachelor” in 2013 and then appeared on two seasons of “Bachelor in Paradise” — got engaged to her boyfriend of four years, Dylan Brown. … That same day, Sydney Hightower — who competed for Peter Weber’s heart on season 24 of “The Bachelor” in 2020 — got engaged to San Francisco 49ers linebacker Fred Warner. … Two days earlier, Haley Ferguson — who competed for Ben Higgins’ heart on season 20 of “The Bachelor” in 2016 and then appeared on three seasons of “Bachelor in Paradise” — accepted a marriage proposal from her boyfriend of a little more than a year, hockey player Oula Palve. (Late last year, her twin sister, Bachelor Nation’s Emily Ferguson, also got engaged to a professional hockey player.) … And “Bachelor in Paradise” alum Lauren Iaconetti took to Instagram on May 6 to announce that she and Hunter McFadden are engaged.
Did Drake break up an engagement? That’s the rumor that started circulating in early May after singer Jamie Sun alleged on Instagram that he and longtime love Naomi Sharon recently split after nearly a decade of coupledom because she was unfaithful. “Imagine having the most beautiful, supportive, and faithful relationship 8 years long with an engagement and wedding planned. A beautiful woman on your side as ride or die. Then this major opportunity comes and a world star calls your fiancée to sign a record deal. Flies you both over and then out of nowhere all the trust is vanished with knives in your back and in your heart. Imagine,” he captioned a since-deleted Instagram post. As for the evidence Drake is the “world star” to whom Jamie was referring? Jamie shared a video of himself working out with Drake (see it here), while Drake’s personal photographer reportedly snapped Naomi in the recording studio during a session for the rapper’s upcoming “Certified Lover Boy” album. Jamie first alluded to the breakup on Instagram in late April.
On May 17, Anya Taylor-Joy was snapped packing on the PDA with Malcolm McRae during an outing in New York City. (See photos here.) It’s unclear how long the “Queen’s Gambit” actress — who was previously linked to photographer Ben “Pip” Seed and to actor Eoin Macken — and the rocker have been an item.
On May 7, Aubrey Plaza casually revealed on Instagram that she’d secretly married her love of a decade, Jeff Baena. While announcing their new collaboration “Spin Me Round” — he co-wrote and intends to direct the indie comedy, while she’s set to star — she referred to him as her “darling husband.” Her rep later confirmed to People magazine that the duo did, in fact, tie the knot, though it’s unclear when exactly they exchanged vows.
On May 17, Deux Moi reported that, according to multiple anonymous sources, Ansel Elgort and his high school sweetheart, ballerina Violetta Komyshan, called it quits again sometime earlier this year. (They briefly split back in 2014.) The news came to light after several spies peeped Violetta dining with Brett Eldredge in Nashville, though Deux Moi’s sources were split over whether or not she and the country music star are dating or just friends.
During an interview with “Entertainment Tonight” that debuted online on May 17, “Dancing With the Stars” pro Gleb Savchenko described himself as “single and ready to mingle,” indicating that his rebound romance with Cassie Scerbo — which followed his late 2020 split from Elena Samodanova — had come to an end. In other “DWTS” breakup news, judge Carrie Ann Inaba took to her Instagram Story on May 12 to announce that she and Fabien Viteri — to whom she was first linked in the summer of 2020 — recently called it quits.
In early April, Us Weekly reported that, according to a source, Luann de Lesseps was “completely smitten” with a man she met while vacationing in Tulum, Mexico, earlier this year. She was finally seen with her mystery man in New York City on May 20. Then over the weekend of May 22, they were snapped packing on the PDA in the Hamptons. (See photos here.) According to a Page Six source, he’s the same man she met in Mexico. They’re reportedly “having a great time” together, though she still “considers herself single and dating.” On May 25, Page Six identified her new beau as Mexico City native Radamez Rubio Gaytan, a chef and former soccer player who once tried out for the Miami Dolphins. “I think she fell madly in love with this one. He flew in from Mexico and he’s been taking her everywhere. … Se’s so happy,” said a second Page Six source.
In other “Housewives” news… On the second part of the “Real Housewives of Dallas” reunion special, which aired on May 11, Brandi Redmond finally addressed the viral video of her husband, Bryan Redmond, kissing another woman. After confirming that it is, in fact, her hubby pictured in the headline-making clip, she revealed that the indiscretion went down in Las Vegas in 2018 during a dual bachelor and bachelorette party for her sister and brother-in-law. The mother of four — who claimed someone leaked the three-year-old video to intentionally cause her harm — said that she and her husband of nearly two decades are still together and trying to work through their issues. Meanwhile, on the first part of the “Real Housewives of Dallas” season 5 reunion, which aired on May 4, Kary Brittingham revealed that she and her husband of more than a decade, Eduardo Brittingham, “decided we needed to go our separate ways” after shooting wrapped.
In mid-May, Mike Esterman told multiple media outlets that his relationship of a few months with Wendy Williams fizzled out due to his busy work schedule. He also said they were “never an item” and only went on three dates. The talk show host was less than thrilled when she heard Mike was running his mouth to the press. On her eponymous talk show, she called him “childish” and griped, “We were never boyfriend and girlfriend, so it wasn’t a thing!” In response to her comments, Mike told Page Six, “Of course she has to have the last word, and because she is the kind of person that she is, she’s the only thing that will make herself look best. … All that I said was I had no time to make any plans when people kept asking when we [would] see each other again, and they took that as a major breakup, which I didn’t even think we had that big of a relationship to begin with other than getting to know each other on a few dates.”
On May 8, Torrey DeVitto took to Instagram to reveal her new boyfriend: Chicago Cubs manager and former professional baseball player David Ross, who came in second on season 24 of “Dancing With the Stars” in 2017. It was the first indication that her quarantine romance with “Blue Bloods” star Will Estes had come to an end. It’s unclear when they called it quits, though David confirmed in early 2020 that he’d finalized his divorce from high school sweetheart Hyla Ross, with whom he shares three children.
On May 22, “Mr. Robot” star Grace Gummer sparked rumors that she and her boyfriend, Mark Ronson, are engaged when she sported a massive diamond sparkler during a PDA-packed outing with the music producer in London. (See photos here.)
On May 14, “Vanderpump Rules” co-stars James Kennedy and Raquel Leviss got engaged during a Coachella-themed bash in Indio, California.
People magazine reported on May 20 that Lindsey Vonn is dating actor and Tequila entrepreneur Diego Osorio. “It’s new and they’re enjoying getting to know each other,” said a source, noting that the duo met through mutual friends. A day earlier, the pair were snapped walking arm-in-arm in New York City. (See photos here.)
On May 5, Page Six broke the news that former “The Bachelor” winner Shayne Lamas — who got engaged to Matt Grant on the finale of season 12 in 2008 and then starred on the reality show “Leave It to Lamas” with dad Lorenzo Lamas — and her husband of 11 years, gossip blogger Nik Richie, recently called it quits. Shayne later confirmed the news to the New York Post’s gossip column, admitting that their “marriage has been empty for years” and that she and her hubby had “not been intimate in almost a year.”
On May 3 — five days after he announced on Instagram that he’d gotten engaged to a woman named Marie — former blink-182 rocker Tom DeLonge returned to the social media platform to reveal they quietly tied the knot in a simple courthouse ceremony “after being engaged for over a year and a half.”
On May 6, Brides magazine revealed that “You” actress Elizabeth Lail married pediatric dentist Nieku Manshadi in front of just 22 guests at Hasbrouck House in Stone Ridge, New York, on April 24, 2021. The uber-private pair got engaged in August 2020.
Tallulah Willis took to Instagram on May 4 to announce that she’s engaged to director Dillon Buss.
The May 9 episode of “90 Day: The Single Life” showed that the rumors from late 2020 were true: Colt Johnson proposed to longtime pal Vanessa Guerra in November after just a month of dating. On the May 23 episode, the duo revealed they’d also eloped: According to Vanessa, the nuptials went down “about a month ago” during a road trip to Reno, Nevada. (It’s unclear when exactly the episode was filmed.) Meanwhile, another “90 Day Fiancé” couple — Armando Rubio and Kenneth Niedermeier — tied the knot at Mansarda winery in Ensenada, Mexico, on May 22.
During an interview with The Sun that debuted online on May 3, “Tiger King” personality John Finlay revealed that in June 2020, he married a woman named Stormey whom he met on a dating app in April 2019. He also said that he, Joe Exotic and Travis Maldonado faked their 2014 three-way wedding, which he called “basically a publicity stunt so Joe could get his own reality TV series.”
Country music singer-songwriter Drew Baldridge married model and dental treatment coordinator Katherine Kraus at Saddle Woods Farm in Murfreesboro, Tennessee, on May 7. According to People magazine, the groom’s cousin, who’s a pastor, officiated the ceremony — during which the bride went barefoot. The duo met back in 2014 and developed a friendship but didn’t take their relationship to the next level until a year and a half later.
“Bringing Up Bates” star Nathan Bates proposed to his girlfriend, Esther Keyes, at a family friend’s home in Orlando, Florida, on May 22.
During an interview with Us Weekly that debuted online on May 4, “Below Deck Mediterranean” alum Bugsy Drake revealed that she has a new boyfriend: a mystery man she met on a yacht with whom she’s been working for “the past year and a half.” She also noted that she and former co-star Alex Radcliffe have “remained close friends” but “work on completely different boats” which is why they’ve “not gone further in our relationship past the friendship.” She added that “you never know what might happen in the future” if they’re ever “on the same yacht again.”
On May 3, famed philanthropists Bill Gates and Melinda Gates took to Twitter to announce they’re divorcing after nearly three decades of marriage. The same day they announced their split, she filed for divorce in King County, Washington. In legal paperwork, she said that the marriage is “irretrievably broken” and that she and Bill — who have a reported net worth of more than $130 billion — do not have a prenuptial agreement and want a judge to divide their assets according to a separation agreement. She also noted in her petition for divorce that “spousal support is not needed.” In the wake of the breakup news, Bill’s past infidelity came to light: He had at least one affair with a Microsoft employee in 2000. On May 16, The New York Times reported that Bill frequently pursued female colleagues over the years.