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 early May 2021, starting with this famous rapper…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 on April 21.
Now keep reading for more of the week's biggest celeb love life updates…
Kathie Lee Gifford revealed there's a new man in her life: "I'm in a really special relationship with somebody that is nice and fun and healthy, and so that's good," she said on the April 29 episode of the "Today" show. "It's just happy, and I don't want to mess it up — and I probably already have by just even mentioning it." She later added of her mystery man, "I've just found somebody that is so much fun to be with. He is challenging to me. He's the smartest person I've ever met, but he's funny. And we have a great time together. And so at this point in my life, that's exactly what I need and exactly what I want, you know? Different seasons of life — we weren't meant to know each other before, it's right now. We don't know what the future holds at all, but we're having fun today."
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Late last month, E! News reported that Kylie Jenner and Travis Scott are just "good friends" who have a "great co-parenting relationship" for the sake of their daughter, Stormi Webster. But on May 5, "Entertainment Tonight" reported that, according to a source, the former couple are now "exploring their relationship romantically again." Said the source, "[They're] messing around and having fun together. They've always had a strong connection and chemistry. … They've been co-parenting so well together and have a lot of love for each other. Everyone around them can see that." The duo sparked the latest round of questions about the nature of their relationship with their flirty behavior while celebrating the rapper's birthday in Miami on May 2.
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On May 4, Us Weekly broke the news that, according to a source, Jennifer Garner and her ex-boyfriend, businessman John Miller, are "back on." The source added that the rekindled romance "started up a few weeks ago." The following day, "Entertainment Tonight" confirmed that, according to a source of its own, the duo "are seeing each other again." Said the "ET" insider, "John has shown Jen that he doesn't care about fame and Jen really likes that about him. He is a down to earth, hardworking guy and they have a strong, natural connection. They relate to each other because they are both very hands-on parents who love their children very much. John has made a big effort to be in Jen's life and they're rekindling their relationship." The pair split in mid-2020 after two years of coupledom. "He was ready for marriage and she just couldn't commit," an Us Weekly source said at the time, adding that the breakup was amicable.
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Sydney Chase isn't backing down from her claims that she hooked up with Tristan Thompson amid his rekindled romance with Khloe Kardashian. On May 1, she took to her Instagram Story to share a screenshot of DMs purportedly sent by Khloe. The messages read, "Hey Sydney, this is Khloe. … I would appreciate if our conversation can remain confidential." (It's possible the screenshot was doctored.) Tristan then sent a cease-and-desist to Sydney, claiming through his lawyer (who also happens to be Khloe's lawyer) that her allegations are "malicious defamatory fabrications" and that he "had no relationship" with her and "never sent" any texts that would indicate they were sexually involved. On May 5, after she received Tristan's cease-and-desist letter, Sydney wrote on her Instagram Story, "I'm moving forward with the truth & am choosing not to comply. … I will not be called a liar."
Bennifer round two? On April 30, Page Six reported that Jennifer Lopez and ex-fiancé Ben Affleck have been spending time together again in the wake of her breakup from Alex Rodriguez. "Security picks him up at a nearby location and drops him off after spending a few hours at her house," said a source. They've reportedly hung out at least three times in recent weeks. But according to a second Page Six source, Bennifer shippers shouldn't get their hopes up for a romantic reconciliation: "They are friends. … They've never not been," said the second source. An E! News source echoed that the exes are "just friends." Confirmed a People magazine source on May 5, "They have a great time hanging out. It's been years since they caught up properly. They have lots to talk about. … They plan on hanging out again." Following his hangouts with J.Lo, Ben made headlines again when a woman named Nivine Jay took to TikTok in early May to reminiscence over the time she matched with the A-list actor on Raya — an uber-exclusive dating app for the rich and famous — but "thought it was fake" and "unmatched him." He then sent her a video on Instagram to confirm his identity: "Nivine, why did you unmatch me?" he asks in a quick clip the beauty shared on TikTok. It's unclear when the interaction took place, though there were reports in late 2019 that the Oscar winner was on Raya.
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.
Did Justin Harley and Sofia Pernas secretly tie the knot? The couple of about a year were photographed wearing what appeared to be wedding bands while drinking on the beach with friends in Malibu on May 1. (See photos here.) The pair have yet to publicly acknowledge a change in their relationship status.
Us Weekly reported on April 30 that Lucy Hale's brief fling with Skeet Ulrich recently came to an end. "It was more of a trial run," said a source. "They wanted to see if they could be more than friends, but it didn't feel right. Skeet was pushing harder, but he's cool with it ending." They reportedly dated for three months.
On April 29, artist Alexis Mixter announced on Instagram that she and Jason Segel had called it quits after eight years of coupledom. "This is a photo of two best friends," she captioned a selfie with the "How I Met Your Mother" alum. "This guy and I have shared so much life together. Changed each other at a soul deep level. All for the better. The depth of our bond was something I could never have anticipated. I've never spent so much time with another person, grown so much alongside someone else, laughed so much, cried so much, shared so much. It is odd to write about the end of a relationship, especially when the friendship that still exists is so full of life. But change happens and we made the decision quite a while ago to let ourselves grow away from what our relationship had been and into what it was becoming. Announcing a breakup on social media is a strange feeling. Some won't understand why it is necessary and that's okay. Having a public romantic relationship is not easy. Ending one feels like navigating a road that doesn't even exist. We are private people when it comes to our personal lives and I intend to keep it that way. My feelings while writing this are only ones of love and gratitude. Gratitude to the universe for putting this man in my life the way it did and then allowing us the grace to decide that what we had, could become more. Because that is what our friendship feels like. More. More than either of us could have asked for in another person. This post is a tribute to love and friendship and those relationships that make life worth living. Thank you J for being my best friend. The person who shares all my favorite jokes, sees who I really am and all I want to be, loves me unconditionally and makes me always strive to be bigger and better than I was yesterday. I will never stop cheering you on with every cell of my body. I will never stop loving you unconditionally."
On April 29, Kat Dennings took to Instagram to share a slideshow of photos of rocker Andrew W.K., which she captioned with a simple black heart emoji. Two days later, she returned to Instagram to share this loved-up selfie revealing they're an item. (It's unclear when exactly they started seeing each other.)
On April 30, multiple media outlets reported that "The Bachelor" alum Cassie Randolph and longtime family friend Brighton Reinhardt finally took their relationship to the next level earlier this year after denying they were a couple in mid-2020. "[They've] been seeing each other since the beginning of the year," said an E! News source. "They recently have become more serious and are dating. Cassie has been really focusing on her school and work transition this year and Brighton has been a huge support system for her." He's also helped her move on from former "The Bachelor" star Colton Underwood. "After last year's events with Colton, she feels she is in a really stable and healthy relationship," said the source. "Things are going well and her family likes [Brighton] a lot. They like to do low-key things and love to be by the beach and cook at home. Cassie is really happy and in a good place." According to an Us Weekly source, "Right now, they're still enjoying spending time with one another and just seeing where things go."
On April 28, former blink-182 rocker Tom DeLonge took to Instagram to reveal he'd gotten engaged by sharing a photo of a woman's hand rocking a hefty engagement ring. Five days later, he returned to Instagram to reveal he and his love, a woman named Marie, quietly tied the knot. "Today, I married my love Marie with a simple little courthouse visit after being engaged for over a year and a half (sorry I only told you all a couple days ago, ha). She is the most amazing person I have ever met. She never judges, totally accepts you for who you are, and is full of love for everyone and everything. She has made everything in my life better, while genuinely supporting my endless quest to create ambitious art and contribute a positive influence to the world as much as possible. She just lets me be free… with her, I feel free. She is the BEST, congrats to us," he captioned a May 3 selfie.
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, separated after shooting wrapped. "This was a really tough season for me and watching it back, I realized how much hurt [I was feeling] and how much I was struggling in my life. As I watched it, I realized how in pain I was. My marriage was falling apart, and I didn't want to admit it," she said. "After the show finished, me and Eduardo had to have a real heart-to-heart talk, and we decided we needed to go our separate ways." (According to an Us Weekly source, the breakup reveal came as a surprise to Kary's co-stars: "Nobody knew it was coming. She kept it quiet the entire time, but it made sense once she told the women," said the source.) Also on May 4, Kary addressed the split on Instagram, captioning a family photo, "Eduardo and I have made the very tough decision to separate. He has been the most amazing father these past 17 years to my four kids and for that I am eternally grateful. We are stepping into this new journey as co-parents together and while I know it's going to be an adjustment, I am confident that we can handle this next chapter of life with the same amount of mutual respect and love we've shared with each other for so long. … Starting over at 50 is scary and change can be hard, but I know that we are doing the right thing for ourselves and our children." Kary and Eduardo share one daughter. He also helped raise her three older children from a previous relationship.
In other "Housewives" news… During an interview with Page Six that debuted online on May 4, Luann de Lesseps described her late-2020 fling with personal trainer Garth Wakeford as a "COVID thing" and said that it was "nice to have male company" while in quarantine. "I felt like I was lucky to meet somebody who I liked," said the "Real Housewives of New York City" star, noting that "nothing big, explosive happened" to end the relationship. "It started with a sizzle and it kind of fizzled," she said. "That's OK, though, because it's spring. Spring is in the air. I'm single. … Third time's the charm, they say, right? I've been married twice. I'm a hopeless romantic. And I feel like, you know, when you're not looking, that's when it happens." She added that there's "no bad blood" between herself and Garth.
Wait, what?! During an interview with the Spanish-language YouTube channel Mirá a Quién Encontré that debuted in late April, "10 Things I Hate About You" director Gil Junger claimed that co-stars Julia Stiles and Joseph Gordon-Levitt dated "for a minute or 10" while shooting the 1999 teen rom-com. "They were very, very attracted to each other, which was cute. She's professing her love to [Heath Ledger's character in the movie] and she's in love with a guy waiting in his trailer to shoot the next scene," said the filmmaker, according to People magazine. "Watching them, it was beautiful how much they enjoyed each other." Gil also implied that Julia said she was thinking about JGL when she delivered the titular poem during the film's emotional climax. "She told me, 'I was just thinking about' that person's name that she was deeply in love with at the time," he said. "It wasn't me, certainly, but it wasn't Heath either. That was one of the magical performances that I've recorded in my lifetime." In "10 Things," Joseph's character pursues Larisa Oleynik's on-screen alter ego, while Julia's character couples up with Heath's.
During an interview with WSJ. Magazine that debuted online on May 5, former "The Bachelor" star Matt James opened up about how he and Rachael Kirkconnell were able to move forward as a couple following her racism scandal: "I think the best way to put it is that we can have critical conversations about being in this relationship and what I need in a partner — especially if that woman isn't Black — to understand what comes with me and my life and being Black," he said. "It's on people who care about being allies to do the work to be truly antiracist. And I think it's unfair to leave people without the ability to unlearn and be better." A day earlier, E! News reported that, according to a source, "Matt and Rachael are working on getting back together but are not putting pressure on their relationship. They are in a great place right now. [They] talk every day and have seen each other multiple times in the last few weeks. … They both want to make it work and are still working on their issues. [They] both want to get back together and be exclusive. They are taking it slow and seeing where it goes." Echoed a second E! source, "The two are working toward finding forgiveness in each other and having conversations about what the future can hold."
On the May 4 episode of "Late Night with Seth Meyers," Jodie Turner-Smith revealed that her relationship with her husband, "Dawson's Creek" alum Joshua Jackson, started off as a one-night stand. "We had a one-night stand. We're in a two-, three-year one-night stand now," she joked. She went on to confirm rumors she was a "Dawson's Creek" fan growing up. (When Seth asked if she was Team Pacey, she replied, "Let's be real: Who wasn't Team Pacey? Let's be real. I mean, no offense to Dawson, but, like, it was all about Pacey.") The "Queen & Slim" actress then detailed the first time she met the former teen heartthrob at a party. (She kept her identity as a fan under wraps until about a month into their relationship, she said.) "I saw him before he saw me, and when I saw him, I was like, 'I want that,'" she recalled. "And then when he saw me, I was pretending like I didn't see him. So he had to yell across the room to me." He used her T-shirt — which referenced a line from the 2018 film "Sorry to Bother You" — as an opening line to strike up a conversation with her. "He comes over and he's like, 'Hey,' and does this really cute, charming thing that he does. And all night he just basically followed me around the party." Clearly, he was picking up on her interest: "He felt the energy. He felt it," Jodie mused.
Kelly Ripa and Mark Consuelos took to Instagram on May 1 to mark their 25th wedding anniversary. "Happy 25th Anniversary to the love of my life. … In the blink of an eye. Because when you know, you know. Thank you for all of the dreams you made reality," the mother of three captioned a collage of photos from over the years. The "Riverdale" actor, meanwhile, captioned a video montage, "'I'll be loving you until the rainbow burns the stars out in the sky… always.' Happy 25th."
On the May 3 episode of "The Voice," Blake Shelton gushed of his fiancée and fellow "The Voice" coach, "It's hard to resist Gwen Stefani. You know, here's this iconic rock star coming to be a coach on 'The Voice' in a black minivan. That was cool to me. … If you had told me back in 1996 that Gwen Stefani was going to be my girlfriend, I would have laughed you out of the room." The country music star proposed to the No Doubt frontwoman back in October.
According to TMZ, Cat Cora's second wife, music exec Nicole Ehrlich, filed for divorce in Los Angeles on April 26 — less than a week after their third wedding anniversary. Last year, the "Iron Chef" and "Around the World in 80 Plates" star made headlines when she claimed in legal documents that her first wife, Jennifer Cora, was trying to "destroy my life at any cost." (Cat and Jennifer, who share four children, divorced in 2015 following 17 years as a couple but just two years of marriage.)
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. "After my engagement to Matt ended … I was devastated and still in search of what I was originally seeking, which was to find love and start a family," Shayne told the New York Post's gossip column when asked for comment on her breakup with Nik. "Shortly after 'The Bachelor' and 'Leave It to Lamas,' I married a man in Vegas after knowing him less than 24 hours on a complete whim. But I can honestly say after 11 years of marriage and two beautiful and thriving children, it was a successful decade. Nik and I are best friends and will continue to raise our children as a team but our marriage has been empty for years. Nik and I have not been intimate in almost a year and it doesn't take a rocket scientist to know that will take a toll on any marriage no matter how much respect you have for each other." She called their decision to separate "pure common sense" and added that what they once had "is no longer there."
Hannah Gadsby revealed on Instagram on April 28 that she secretly married producer Jenney Shamash back in January. "I would like to introduce all y'all to Jenney Shamash. She is a producer extraordinaire. She is very funny and is really talented at reciting facts. It is a joy to behold. We got married in January and we are very chuffed about it. For the record: this is me gushing. I am full of very positive feelings. This is a nice story. My heartfelt thanks to everybody who voted for marriage equality. #married #really? #yeahtotally," the Emmy-winning comedian captioned a slideshow including this shot with her new missus.
Tallulah Willis took to Instagram on May 4 to announce that she's engaged to director Dillon Buss. "With absolute most certainty," she captioned a slideshow of photos depicting the proposal. Dillon, meanwhile, captioned a slideshow of his own, "I can finally call you my fiancée. Love you forever Buuski Lu, you are my best friend.
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. "My wedding was the happiest day of my life," he said, adding that he and his missus delayed their nuptials amid the coronavirus pandemic but ultimately decided to exchange vows at a courthouse. "I've never felt this way about anyone before," he gushed. "I had no idea what it is like to marry your rock, your soulmate, the person you spend every minute of the day with. Stormey completes me and we are deeply in love." He also said that he, Joe Exotic and Travis Maldonado faked their 2014 three-way wedding. "My fake wedding didn't feel right at all. This is a totally different feeling," he said. "The fake one was basically a publicity stunt so Joe could get his own reality TV series. This [wedding] was the real thing." His wife is apparently aware of his past: "I told her everything because she was that important to me. I was nervous because most people would run away screaming. But she stuck with me, and that showed she is The One," he said. John added that his "only short-term goal" is to cover up his tattoos dedicated to the imprisoned "Tiger King" star.
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: "It's not in any sort of a stage right now that I feel it's important to make public at this point in time. But I am seeing someone that I did meet on a yacht, so it's been a lot of fun and he's a great guy," she said, adding that she and her new beau have been working together for "the past year and a half." As for former co-star Alex Radcliffe, "We've remained close friends for sure," she said. "We work on completely different boats. We're never really in the same place a lot of the time. … We've obviously not gone further in our relationship past the friendship because of that. We don't see each other much, but you know, you never know what might happen in the future. If we get on the same yacht again, that would be kind of fun."
On May 3, famed philanthropists Bill Gates and Melinda Gates — who founded the Bill & Melinda Gates Foundation in 2000 — took to Twitter to announce they're divorcing after nearly three decades of marriage. "After a great deal of thought and a lot of work on our relationship, we have made the decision to end our marriage. Over the last 27 years, we have raised three incredible children and built a foundation that works all over the world to enable all people to lead healthy, productive lives," they wrote in a joint statement. "We continue to share a belief in that mission and will continue our work together at the foundation, but we no longer believe we can grow together as a couple in this next phase of our lives. We ask for space and privacy for our family as we begin to navigate this new life." The same day they announced their split, Melinda 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."