DWTS' Jackson Olson & Pat Sajak's Daughter Maggie Share Disney Date
Jackson Olson and Maggie Sajak are hitting their relationship out of the park.
Indeed, the Savannah Bananas baseball player and his girlfriend—the daughter of former Wheel of Fortune host Pat Sajak and his wife Lesly Brown Sajak—created their own magic while on a special trip to Disney World.
In a video shared to Instagram June 17, Jackson—who will be part of Dancing With the Stars’ season 35 cast—looked at the camera and mouthed sarcastically, “I wish I had a girlfriend to go to Disney with, that would be so fun.”
Then, the clip panned to Maggie, who similarly mouthed, “Yeah I wish I had a boyfriend to go with, how cool would that be.”
After the pair joined hands, the video—set to Taylor Swift’s song “Opalite”—featured clips of them laughing as they rode the Disney rides and smiling as they shared treats across the park. Not to mention, they twinned with matching Grape Soda pins as a nod to Pixar’s 2009 love story Up.
Since Jackson, 28, and Maggie, 31, hard launched their relationship in April, they have shared more glimpses inside their romance, like when she attended a Savannah Bananas game last month.
Meanwhile, the Georgia-based athlete recently detailed how he and the Los Angeles-based influencer—who works at Wheel of Fortune as a social correspondent—make their long-distance relationship work.
“It’s just about planning and making sure you’re setting aside time to see each other and make really cool experiences happen,” he told Us Weekly last month. “You only get one chance at a start of a relationship.”
As he described it, “We’re able to come together and just have an awesome relationship.”
And that also includes bonding with Maggie’s parents Pat and Lesly. As for how Jackson felt after meeting the legendary Wheel of Fortune host?
“He’s a great guy,” he added. “Everybody’s nervous to meet the father of the person they’re dating, or mother or both.”
Plus, he noted there is a freedom to having been his authentic, “weird” self with Maggie’s dad.
“I’m not going to hold back who I am as a person, and people seem to enjoy that company,” Jackson said. “I’m happy that I’m able to be myself truly in every aspect now.”
Ahead of Jackson’s appearance on Dancing With the Stars, read on to check out relationship details about other contestants from the show.
The season 33 partners dated for about seven months between 2024 and spring 2025.
Showmance or Real Deal: Real deal.
In April 2025, the fellow DWTS pros kissed on the lips onstage on the final night of the series' 2025 tour during their show-closing duet dance, confirming months of romance rumors.
Showmance or Real Deal: Real deal, as their colleague Ezra Sosa wrote "FINALLY" in response to a fans' video of the pair's smooch.
The former Bachelorette and the Jersey Shore star stoked dating rumors during their time competing against one another on season 31, thanks to their flirtations on social media and coy responses when asked about their possible romance.
"You get to know the other celebrities on Dancing with the Stars," Gabby told E! News in December 2022. "So, we formed a friendship right away and I feel like our senses of humor are really similar. I was so tunnel vision during the competition. I was like, 'I'm here to win' and I didn't have room for anything else. So, we live in different states, but we are having fun. We'll see."
Showmance or Real Deal: Forget GTL, this one was DOA. The pair never ended up officially dating and Gabby debuted her romance with comedian and TV writer Robby Hoffman in August 2023. The pair wed in January 2025.
Months after placing fifth in the 31st season of the dance show, the couple confirmed their romance on Valentine's Day 2023. "My Valentine," the CODA actor captioned a selfie with the choreographer. "Happy Valentine's Day!"
Britt and Daniel then announced their engagement in December 2023 and married in front of a trouple of DWTS pros in August 2025.
Showmance or Real Deal: Real deal.
While she was partnered with Hayes Grier, the two hit it off during season 21's Switch Up week, with Alek calling her "so hot." After her elimination, Emma spilled that she and Alek had yet to go on a date, saying, "We'll see."
Showmance or Real Deal: Given Alek's tendency to blush and avoid answering questions about his feelings for Emma, telling E! News "no comment!" we think this crush was very real. But Emma danced herself off the market following Skarlatos' 2015 run, so if it was real, it wasn't that real.
The dance pro and Bachelorette alum were romantically linked while competing together on DWTS' season 33 in 2024. However, their offscreen chemistry fizzled out by June 2025 shortly after Jenn returned to Miami to finish her master's degree.
Showmance or Real Deal: Unconfirmed.
Which bring us to these two. After dating a little on and off since 2011, the pros got engaged live on the show in October 2016, and were married in March 2018. However, in Aug. 2022, E! News confirmed that after four years of marriage, Slater and Farber were going their separate ways.
Showmance or Real Deal? Despite the outcome, they were still the real deal and have remained close friends and cordial co-stars after their split.
"It's not a nightmare at all," Emma exclusively told E! News. "We support each other so much that I want the very best for Sasha. We support each other, very, very truly."
Val and Jenna were dating in 2015, before she was promoted to pro dancer. They got engaged in June of 2018 before making it official and walking down the aisle in April of 2019. In July 2022, they announced they were expecting their first baby together. The two welcomed son Rome Valentin in January 2023.
"Life is awesome," Val told E! News in May 2023. Becoming a dad "definitely elevated my joy for life, my joy for my family, and every day I learn something new being a father."
Showmance or Real Deal? Real deal, y'all!
In December 2020, E! News learned the Selling Sunset star was dating the Dancing With the Stars pro after they had competed separately on season 29.
However, after two months of dating, E! News exclusively confirmed they had called it quits. At the time, a source close to the realtor said, "They had a fun time together but in the end, decided it would be best if they part ways. They are still friendly and cordial. It wasn't a messy breakup, just wasn't the right fit or right timing."
Chrishell has since found love with partner G Flip.
Showmance or Real Deal: We're calling Chrishell and Keo's romance the real deal.
Platonic throughout their seventh-place-finishing 2017 run, the Total Bellas star and the former Dancing With the Stars pro found their way back to each other after her split from John Cena in 2018. Nikki confirmed her relationship with Artem in May 2019, and they got engaged later that year.
The WWE Hall of Famer learned she was expecting soon after their Paris engagement, with them welcoming son Matteo Artemovich Chigvintsev in 2020.
Sadly, though, the pair are no longer partnering up. Nikki filed for divorce in September 2024, two weeks after Artem was arrested on suspicion of domestic violence. Ultimately, the Napa County District Attorney's office announced they decided not to file charges against him "after a thorough review of the criminal investigation and careful evaluation of the evidence presented to the DA’s Office."
Nikki and Artem settled their divorce in November 2024, with her rep noting the two also dropped their "the domestic violence restraining orders against each other in an effort to move on with their lives and effectively co-parent their son."
Showmance or Real Deal? Real deal.
Model Alexis and relatively new pro Alan flirted up a storm throughout season 27, and Ren had admitted on the show that she had a crush on him. At the time, a source even told E! News that they "really enjoy each other's company" and were "seeing where things go."
Showmance or Real Deal? Largely for the cameras, unfortunately. Multiple outlets reported their split in December 2018, blaming it on long-distance and demanding schedules.
The professional dancers got engaged on Dec. 5, 2015 after dating since 2012. Maks proposed onstage at the SWAY: A Dance Trilogy event in Miami. Six months after welcoming their son Shai, the lovebirds exchanged vows during a lavish ceremony in July 2017. They then welcomed baby Rio in June 2023 and their third son Milan in July 2024.
Showmance or Real Deal: A match made in DWTS heaven!
The partners struck up a romance in season five, but broke up a few months after their shocking exit. Still, Sabrina and Mark remained friendly, with The Cheetah Girls star even returning to the ballroom to cheer for him the following season.
Showmance or Real Deal: Real deal.
Funnily enough, the duo had gone out on several dates before he even signed up for the show. And while they denied any romance rumors during season 18, that didn't stop them from playing up their chemistry during performances.
Showmance or Real Deal: Total showmance.
Soon after the Shark Tank star announced he was separating from his wife of 14 years Diane Plese, sources confirmed to E! News that he and Kym Johnson, his pro partner from season 20, were dating and "really happy together."
While Robert and Kym at first played coy about the nature of their relationship, that quickly stopped. They were engaged in February 2016, married by June 2016, and welcomed twins in April 2018.
Showmance or Real Deal: Very, very, very real.
Partnered in season three, Karina and Mario quickly struck up a romance, which went on for two years, before they called it off for good in 2008. "The relationship wasn't heading in the right direction," Smirnoff's rep said in a statement, after rumors of infidelity on Lopez's part.
Showmance or Real Deal: Real deal.
The professional dancers got engaged in 2009 following just six months of dating, shortly after her split from Mario Lopez. Sadly, they called it off later that same year. But the duo remained friendly, even going on vacations together.
Showmance or Real Deal: Real deal.
Married since 2014, the pros announced the arrival of their daughter Nikita in May 2023.
Daniella shared the happy news by posting a photo and video of Pasha with Nikita to Instagram Stories. She wrote "daddy's girl" alongside the clip and "My Geminis" beside the picture.
Showmance or Real Deal: Real deal, baby!
After showing off their insane chemistry during the sixth season, the duo dated for nearly a year before announcing their 2009 breakup in the most cordial way ever: matching tweets! "Hi everyone, we wanted you all to know directly from us, that Shannon & I have decided to end our relationship as boyfriend & girlfriend...," Derek tweeted that August. Finished Shannon, "However, we love and care about each other very much and will remain friends and in each others lives."
Derek is now married to his dance partner Hayley Erbert.
Showmance or Real Deal: Real deal.
Though they dodged questions about their reported romance during season 18, a source told E! News that the eventual champs were just friends.
Showmance or Real Deal: This time, 'twas a showmance.
While they never technically dated, it didn't stop him from trying to woo his professional partner during season 10, even buying her gifts like a diamond necklace and a diamond ring, which she eventually gave back. "We had a fling," Cheryl later told Wendy Williams. "A little flirty fling. Like, a little flirt, flirt. That's it."
Showmance or Real Deal: Showmance!
One of DWTS' most playful pairings, rumors continued about their relationship for all of season 10. And they weren't doing anything to stop them! Seriously, they staged an almost-kiss on a bed for one of their finale performances. Their banter continued eight cycles later when Erin signed on as the show's co-host.
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.
While rumors ran rampant that the duo struck up a romance during season 17, the Pretty Little Liars star always denied that he was dating Peta.
Showmance or Real Deal: Showmance!
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