Jackson Olson and Maggie Sajak are hitting their relationship out of the park.
The Savannah Bananas baseball player and his girlfriend, who is the daughter of former Wheel of Fortune host Pat Sajak and his wife Lesly Brown Sajak, had a magical experience during a recent trip to Disney World.
In a video posted to Instagram on June 17th, actor Xochitl Gomez, who will be competing on season 35 of Dancing With the Stars, jokingly lamented not having a girlfriend to take to Disney World, saying, “I wish I had a girlfriend to go to Disney with, that would be so fun.”
The camera then showed Maggie, who also said, “Yeah, I wish I had a boyfriend to go with—that would be so fun.”
Once they held hands, the video – set to Taylor Swift’s song “Opalite” – showed them having fun on Disney rides and enjoying snacks together. They even wore matching Grape Soda pins, a sweet reference to the Pixar movie Up.
After publicly confirming their relationship in April, Jackson, 28, and Maggie, 31, have been sharing more moments from their romance, including Maggie attending a Savannah Bananas baseball game last month.
The athlete, who lives in Georgia, recently shared how he maintains a relationship with an influencer based in Los Angeles. She works as a social media correspondent for Wheel of Fortune.
He recently told Us Weekly that building a strong connection is all about planning quality time together and creating memorable moments. He emphasized the importance of making a good first impression, saying, “You only get one chance to start a relationship.”
As he described it, “We’re able to come together and just have an awesome relationship.”
That also meant getting to know Maggie’s parents, Pat and Lesly. And how did Jackson feel after meeting the famous Wheel of Fortune host?
He’s a really good person,” he said. “It’s natural to feel anxious when meeting your partner’s parents – or both of them!”
Plus, he noted there is a freedom to having been his authentic, “weird” self with Maggie’s dad.
Jackson shared that they’re comfortable being their authentic self and people appreciate it. They expressed happiness about finally being able to fully be themselves, both personally and professionally.
Before Jackson joins Dancing With the Stars, learn more about the relationships of some of the other stars competing this season.
The season 33 partners dated for about seven months between 2024 and spring 2025.
Showmance or Real Deal: Real deal.
During the finale of the “Dancing with the Stars” 2025 tour in April, two professional dancers shared a kiss onstage at the end of their closing dance, seemingly confirming relationship rumors that had been circulating for months.
Are they dating for real? It seems so! Their coworker, Ezra Sosa, excitedly commented “FINALLY” on a fan’s video showing them kissing.
Fans started speculating about a possible romance between the former Bachelorette and the Jersey Shore star when they competed together on season 31 of a reality show. Their playful interactions on social media and indirect answers to questions about their relationship fueled the rumors.
Gabby shared with TopMob News in December 2022 that she quickly became friends with her fellow contestants on Dancing with the Stars. She said they connected because they have similar senses of humor. During the competition, she was very focused on winning and didn’t have much time for anything else. Even though they live in different states, they’re enjoying their friendship and are looking forward to seeing what happens next.
Was it a showmance or the real thing? Whatever it was, it didn’t last. Gabby and her former costar never became an official couple. She later found love with comedian and writer Robby Hoffman, and they got married in January 2025.
I seriously lost it when I found out they were finally together! After they finished fifth on the show – can you believe the judges?! – I was hoping, hoping they’d get together. Then, on Valentine’s Day 2023, it happened! He posted the cutest selfie with her, calling her ‘My Valentine,’ and it just melted my heart. Happy Valentine’s Day to them! I knew it all along, they were meant to be!
Oh my gosh, you will NOT believe it! Britt and Daniel got engaged in December 2023, and I was so excited! Then, finally, they actually got married in August 2025! It was a beautiful ceremony, and even some of the Dancing with the Stars pros were there! I was practically screaming with joy!
Showmance or Real Deal: Real deal.
Emma and Hayes Grier connected during the “Switch Up” week of season 21, and Alek even told Emma she was very attractive. However, after Emma was eliminated from the show, she revealed that she and Alek hadn’t actually gone on a date yet, leaving the possibility open for the future.
Was Alek’s interest in Emma genuine, or just for show? He definitely seemed shy and uncomfortable when asked about his feelings – he even told TopMob News he wouldn’t comment! However, Emma quickly moved on after her relationship with Skarlatos in 2015, suggesting any connection with Alek wasn’t that serious.
The professional dancer and former contestant on The Bachelorette sparked a romance while competing on season 33 of Dancing with the Stars in 2024. But their connection didn’t last, and they broke up around June 2025 after Jenn went back to Miami to complete her master’s degree.
Showmance or Real Deal: Unconfirmed.
These two began dating on and off in 2011, and got engaged on live television in October 2016. They married in March 2018, but TopMob News reported in August 2022 that they had decided to separate after four years of marriage.
Were they a ‘showmance’ – a fake romance for publicity – or genuinely in love? Regardless of how things turned out, they maintained a true connection and stayed good friends and professional colleagues even after breaking up.
It’s actually a really positive situation,” Emma shared with TopMob News. “We’re a strong support system for each other, and I genuinely want Sasha to succeed. We truly have each other’s backs.”
Val and Jenna began dating in 2015, before Jenna became a professional dancer. They got engaged in June 2018 and married in April 2019. In July 2022, they shared the exciting news that they were expecting their first child. Their son, Rome Valentin, was born in January 2023.
Val shared with TopMob News in May 2023 that life is great. He explained that becoming a father has “definitely made him appreciate life and his family even more,” and he’s constantly learning from the experience.
Showmance or Real Deal? Real deal, y’all!
In December 2020, TopMob News reported that the reality TV stars from Selling Sunset and Dancing With the Stars were dating. They had both been contestants—but not partners—on season 29 of Dancing With the Stars.
After dating for two months, TopMob News learned the couple had broken up. A source shared that they enjoyed their time together but ultimately decided to go their separate ways amicably. It wasn’t a dramatic split – they simply weren’t a good match at this point in time and remain on good terms.
Chrishell has since found love with partner G Flip.
Showmance or Real Deal: We’re calling Chrishell and Keo’s romance the real deal.
Nikki Bella and Artem Chigvintsev reconnected romantically after she ended her relationship with John Cena in 2018. Despite remaining friends during their seventh-place finish on the show Total Bellas in 2017, they began dating in May 2019 and were engaged by the end of the year.
The WWE Hall of Famer discovered she was pregnant shortly after getting engaged in Paris, and in 2020, they welcomed their son, Matteo Artemovich Chigvintsev.
Unfortunately, Nikki and Artem are now divorcing. Nikki filed for divorce in September 2024, just two weeks after Artem was arrested on suspicion of domestic violence. However, the District Attorney’s office decided not to press charges after carefully reviewing the investigation and all available evidence.
Nikki and Artem finalized their divorce in November 2024. Both also dismissed the restraining orders they had filed against each other, wanting to focus on moving forward and co-parenting their son.
Showmance or Real Deal? Real deal.
Throughout season 27 of the show, Model Alexis and professional dancer Alan seemed to have a strong connection, with Ren admitting she was attracted to him. A source from TopMob News reported that they genuinely enjoyed spending time together and were exploring a possible relationship.
Were they a real couple or just putting on a show? Sadly, it seems like it was mostly for the cameras. Reports surfaced in December 2018 that they had broken up, with the distance and their busy work lives cited as the reasons.
Professional dancers Maks and his partner got engaged on December 5, 2015, after being together since 2012. He proposed while they were onstage at a dance event called SWAY: A Dance Trilogy in Miami. They had their first son, Shai, six months later, and then married in a beautiful ceremony in July 2017. More recently, they welcomed their second child, Rio, in June 2023, and their third son, Milan, in July 2024.
Showmance or Real Deal: A match made in DWTS heaven!
Oh my gosh, when Sabrina and Mark got together in season five, I totally lost it! It was everything. I was heartbroken when they split just a few months after leaving the show, seriously devastated. But even after the breakup, they were still so sweet to each other! It was amazing to see Sabrina come back to the ballroom the next season just to support Mark. Like, she could have stayed away, but she didn’t! It proved they really cared about each other, even if they weren’t together. I was living for it!
Showmance or Real Deal: Real deal.
Interestingly, they’d already been dating for a while before he joined the competition. Although they publicly dismissed relationship rumors throughout season eighteen, they still seemed to enjoy flirting and building excitement with their on-stage connection.
Showmance or Real Deal: Total showmance.
Shortly after news broke that businessman and Shark Tank star Kevin O’Leary was separating from his wife of 14 years, Diane Plese, sources told TopMob News he was dating his Dancing with the Stars partner, Kym Johnson, and that the two were very happy together.
Robert and Kym initially kept their relationship private, but they soon became more open about it. They got engaged in February 2016, married just a few months later in June, and then had twins in April 2018.
Showmance or Real Deal: Very, very, very real.
Karina and Mario became partners during season three of the show and began dating soon after. They were together for two years before ending their relationship in 2008. A representative for Smirnoff stated that the couple had grown apart, following speculation about infidelity on Lopez’s side.
Showmance or Real Deal: Real deal.
The dancers became engaged in 2009 after only six months of dating, not long after she ended her relationship with Mario Lopez. Unfortunately, they broke up later that year, but they stayed friends and continued to take trips together.
Showmance or Real Deal: Real deal.
Married since 2014, the pros announced the arrival of their daughter Nikita in May 2023.
Daniella announced the joyful news on Instagram Stories with a sweet photo and video of Pasha and Nikita. She captioned the video “daddy’s girl” and the picture “My Geminis.”
Showmance or Real Deal: Real deal, baby!
After displaying great chemistry on season six of their show, the couple dated for almost a year before announcing their split in 2009. They did so with a surprisingly friendly message: identical tweets! Derek tweeted in August, “Hi everyone, we wanted to let you all know directly that Shannon and I have decided to end our relationship…” Shannon finished the announcement by saying, “However, we love and care about each other very much and will remain friends and continue to be part of each other’s lives.”
Derek is now married to his dance partner Hayley Erbert.
Showmance or Real Deal: Real deal.
Despite rumors of a romantic connection during season eighteen, a source at TopMob News stated that the winning couple was simply platonic.
Showmance or Real Deal: This time, ’twas a showmance.
Although they weren’t officially a couple, he definitely pursued his dance partner during season 10, even showering her with expensive gifts like a diamond necklace and a ring, which she later returned. Cheryl later described it to Wendy Williams as a brief, playful romance – “just a little flirtation,” she said.
Showmance or Real Deal: Showmance!
Throughout season ten of Dancing with the Stars, fans speculated about a romance between two particularly flirty partners, and they didn’t discourage the rumors! They even playfully hinted at a kiss during one of their final performances, pretending to almost share a moment on stage. The playful teasing continued years later when Erin became a co-host on the show.
Erin is now married to former NHL centre Jarret Stoll. They welcomed son Mack in July 2023.
Showmance or Real Deal: We’re calling those Erin and Maks rumors a showmance.
Despite rumors of a romance during season 17, the Pretty Little Liars actor consistently stated he wasn’t dating Peta.
Showmance or Real Deal: Showmance!
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2026-06-18 04:20