Pat Sajak’s Daughter Maggie Sajak Debuts Romance With Jackson Olson

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Maggie Sajak has come into some good fortune. 

Pat Sajak’s daughter has recently gone public with her relationship with Jackson Olson, a player for the Savannah Bananas baseball team.

Jackson shared a cute photo of the pair posing in front of Cinderella’s castle at Disneyland on April 21st, and playfully captioned it, “Applications are now closed.”

I was absolutely cracking up last year when one of the Banana Ball players posted this funny video online! He was basically asking social media to help him find a girlfriend, and he did it with this hilarious ‘boyfriend application.’ It was such a clever and amusing way to put himself out there!

In a recent TikTok video, Jackson revealed they’ve been single for more than five years and are now ready to find someone. They jokingly announced they’re accepting applications for a boyfriend starting in 2026.

Jackson’s strengths included his passion for Disney, Taylor Swift’s music, and musicals. He also dances on baseball fields as part of his job in a performing sports league, which he jokingly refers to as his livelihood.

He also jokingly mentioned his parents are eager for him to find a girlfriend, saying they’ve been giving him a lot of encouragement – and gentle pressure – to start dating.

Beyond his talent, Jackson revealed he still enjoys building with Legos and jokingly admitted to eating like a kid. He also confidently declared he’d be an excellent Instagram boyfriend.

“I’m very unphotogenic,” he added, “So I’ll make you look great in photos.”

Maggie, who dated Ross McCall earlier in 2024, really caught people’s attention on the show. Meanwhile, Jackson received a lot of supportive responses after asking for connections on social media.

As one TikTok user joked in the comments, “Green flag after green flag.”

Meanwhile, another teacher influencer’s comment earned a like from Jackson himself. 

“If I was 20 years younger,” she joked. “Best of luck. You are so fun!”

Following the public reveal of his relationship with the Wheel of Fortune social correspondent, Jackson playfully shared a clip from the movie Elf. The clip features Will Ferrell, as Buddy the Elf, enthusiastically declaring, “I’m in love, I’m in love and I don’t care who knows it!”

Alongside the clip, Jackson joked, “Me right now.”

For more stars who have hard launched their romance on social media, keep reading… 

Okay, so everyone’s buzzing about Zara and Louis finally confirming they’re a couple! They officially went public with their relationship in August 2025, which is so sweet – it was about six months after people started wondering if they were dating. Zara posted an adorable selfie of them being affectionate on her social media, just with a heart, and Louis replied with a simple ‘I love you x’. It’s lovely to see them so happy and open about things!

Luke Newton and Antonia Roumelioti have confirmed they are dating. Newton shared a photo on Instagram on May 9th of Roumelioti kissing him on the cheek. The couple, who were first linked in June 2024, made a public appearance together at the pre-BAFTA TV Awards party hosted by British Vogue and Netflix.

Gigi Hadid confirmed her relationship with Bradley Cooper by sharing a photo of them kissing at her 30th birthday party on May 3rd, a week after the event. She celebrated the milestone birthday on Instagram, writing about how grateful she is for all of life’s experiences – the good and the bad – and for the amazing people in her life, including her role as a mom, friend, partner, and daughter. Gigi and Bradley began dating in 2023, but only recently revealed their relationship to the public. In an interview with Vogue on March 11th, Gigi described their connection as “very romantic and happy.”

Ice Spice shared a glimpse of her relationship with Sauce Gardner in a recent photo, including a mirror selfie posted on April 29th. Rumors about the couple began in September when Ice Spice went to a New York Jets game, and they’ve been seen together since, including at the 2025 Vanity Fair Oscars Party.

Lucas Bravo and Shailene Woodley have publicly confirmed their relationship with photos from a trip to Slab City, California. Bravo shared a series of pictures in April 2025 showing the couple holding hands in the desert, wearing cowboy hats, and posing with Sophie Hawley-Weld of the band Sofi Tukker. This follows Lucas telling People magazine just a month prior that he was “really happy.” Rumors of their romance began when they were photographed on a romantic walk in Paris, with Lucas holding Shailene’s hand.

I was so excited to finally see Inka Williams and Channing Tatum make things official on Instagram! It’s been a couple of months since they were first spotted together at the Oscars after-party, and this post just confirmed what we all knew – they’re totally smitten. She shared a sweet Instagram story wishing him a happy birthday, and you can see him kissing her forehead in the pic! Her caption was just adorable – she called him the ‘handsomest, kindest, funniest, stoopidest most gorgeous human ever’ and thanked him for making life more beautiful. It’s so lovely to see them so happy together!

Madelaine Petsch and Tyga confirmed their relationship on Instagram with photos shared by the Riverdale actress on April 21st. The pictures showed them together at Coachella, including one of Madelaine resting her head on Tyga’s shoulder and another of them hugging under the stars. Rumors about the couple began in February when they were seen together at a Los Angeles Lakers basketball game. They were also spotted at Vanity Fair‘s Young Hollywood party later that month.

Nicola Coughlan, known for her role in Bridgerton, subtly confirmed she’s dating Jake Dunn in a February Instagram post. She wished the Renegade Nell actor a happy birthday and shared a photo of him on her Instagram Stories. Rumors about the couple began last summer at the All Points East festival, and were further fueled by sightings of them together in London in recent months.

Just one month after finalizing his separation from Britney Spears, Sam Asghari publicly announced his new relationship with Brooke Irvine, posting heartwarming photos to celebrate the new year.

Katie Maloney confirmed her relationship with Nick Martin on Instagram in December with a touching birthday post featuring a photo of them together. Nick shared the same picture, playfully calling it their “Casa Vega Xmas Card.” While she had kept his identity a secret beforehand, Katie had previously told fans she was in love. In an October episode of her friend Dana Kathan’s podcast, Disrespectfully, Katie revealed, “I have a boyfriend. He just makes me feel really special, and he’s really special.”

Okay, so things are definitely heating up for Joe Manganiello! He’s officially introduced the world to his new girlfriend, Caitlin O’Connor – they made their red carpet debut back in December, and he’s now sharing sweet moments from their time together. It’s a lovely new chapter for him, especially after announcing his divorce from Sofia Vergara after seven years of marriage last year. He recently posted a ‘week in review’ with some adorable photos of him and Caitlin, including a really cute selfie of her with flowers and a heart-shaped candy box. It’s clear he’s happy, and it’s lovely to see!

Halsey and Avan Jogia confirmed they are dating with a Halloween post in 2023, putting an end to speculation. The photos showed Halsey holding Avan’s hand while facing away from the camera. They were first seen kissing on a date in Hollywood a month earlier, and now they’re engaged! Halsey confirmed the news in September by responding to a post on X about her hoping to marry Avan, simply calling him her “fiancé.”

Jana Kramer publicly revealed her relationship with soccer player Allan Russell in January 2023 with a happy photo of them together, captioning it “Back where it all started.” More than a year later, in July 2024, they got married in Scotland. However, she later shared that they had actually legally married in January of that same year. Jana, who also has children Jolie and Jace with her ex-husband Mike Caussin, explained on her Whine Down podcast in March 2025 that they wanted a private moment just for themselves before announcing it to the world. The couple share a son named Roman Russell.

In October 2022, Charlie Puth revealed on the Howard Stern Show that he was dating someone and was “definitely” in love. He later shared the identity of his new partner, Brooke Sansone, in a December Instagram post celebrating his 31st birthday. He posted pictures of them kissing in a photo booth with a playful caption about not being a “loser” for having found her. Charlie Puth and Brooke Sansone got married in September 2024.

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2026-04-22 16:17