The Strangest Things About Zooey Deschanel And Jonathan Scott's Relationship

Ever since Zooey Deschanel and Jonathan Scott started dating in 2019, they've not stopped gushing about one another. The former "New Girl" actor and "Property Brothers" star are extremely vocal about their love, often enthusing about their romance by sharing the sweetest sentiments with the world. "I waited my whole life to find Zooey, and I've now waited my whole life to have my dream home with someone like Zooey," Jonathan said on "Today" in 2022. And Deschanel is equally quick to get lovey-dovey. "5 years ago today I was lucky enough to go on a first date with this total dreamboat person. Here we are and he's still making me smile every day," she wrote on Instagram in August 2024 to celebrate their anniversary.

But, as we learned from the red flags in Blake Lively and Ryan Reynolds' marriage, even the romances that seem the most perfect from the outside have a few oddities. Deschanel and her man are no different, because there are some pretty strange things about their partnership we just can't ignore.

It's awkward enough to meet someone you like for the first time, but meeting them on TV alongside your sibling while being recorded? That's one strange way to start a romance. Twee trailblazer Zooey Deschanel and Jonathan Scott know that all too well, as they were introduced in August 2019 while filming "Carpool Karaoke" alongside her sister Emily Deschanel and his brother Drew Scott. She and her future fiancé sat in the front as she took the wheel, and both admitted they struggled to hide their affection for each other. Deschanel told Drew Scott and his wife Linda Phan on "At Home with Linda & Drew Scott" in 2020 that she was flirting with Jonathan and knew he was flirting back. Jonathan joked on the podcast, "I thought I was playing it cool. I didn't think anything of it. The producer said I was flirting so bad, so hard, they had to cut a bunch of that out." Drew then joked, "Otherwise, you looked like a creepy weirdo."

But even when Deschanel and Jonathan were ready to enjoy some time alone on their first proper date, that started out awkward too. She wasn't even sure it was a date because Jonathan asked her out and later messaged to see if she was attending alone. "He said, 'Are you bringing people?' and I was like, 'No, just me,'" she said. "And then I was like, 'Should I bring people? Should I call my sister?'" The first date turned out to be unconventional anyway, as they visited an escape room.

The timing of Zooey Deschanel and Jonathan Scott's relationship raised a few eyebrows, as the "Elf" star was still legally married to Jacob Pechenik — her second husband after Ben Gibbard — when their romance began. The exes announced their separation in a September 6, 2019 statement, which read (via Us Weekly), "After much discussion and a long period of contemplation we have decided we are better off as friends, business partners and co-parents rather than life partners."

But, as their breakup hit headlines, the Emmy nominee had already moved on with the HGTV star. Just seven days later, Hollywood Life reported Deschanel and Jonathan were dating (he later confirmed their anniversary to be August 4). They didn't care who saw them out either, as they enjoying a public date night at a California restaurant. "Zooey and Jonathan kept looking at each other and smiling and sat closely, cuddling constantly throughout their meal," an onlooker said. "They seemed giddy about one another and held hands as they arrived and whispered to each other often." Pechenik filed for divorce on October 22, 2019, but a People source denied any overlap between the two relationships. "They have been separated for several months. They are very private and are excellent parents and love their kids so much and want this to be smooth for them," the insider said.

Despite Zooey Deschanel and Jacob Pechenik not starting divorce proceedings, she didn't mind jumping headfirst into her relationship with Jonathan Scott — and things moved quickly early on. On October 21, 2019, Deschanel confirmed she'd met the other Property Brother when she made things Instagram official with her new man following a date night with Drew Scott and Linda Phan. The foursome enjoyed a night out at Halloween Horror Nights, and Jonathan cradled his new love as they posed together. The following month, the "500 Days of Summer" star had been further welcomed into the Scott family. Deschanel attended Jonathan and Drew's brother JD Scott's quirky wedding as her boyfriend's plus one, and the two got into the spirit in almost matching dark Batman and Catwoman costumes.

There's nothing wrong with throwing caution to the wind and letting yourself be in love sometimes, but, as therapist and relationship coach Matthew Pfifer told Bolde, it's imperative to see people at their best and worst before making big life decisions. "When you're in the honeymoon phase, you're only seeing the best parts of the other person. You haven't had any fights yet or seen each other when you're tired or stressed," he said. "...It's important to take things slow in the beginning and get to know the other person before getting too emotionally attached." For these two though, a fast-moving start clearly worked.

Though Zooey Deschanel and Jonathan Scott's relationship progressed quickly early on, strangely, things then slowed down a lot. Jonathan didn't pop the question until August 2023, four years after they started dating. Equally odd? Despite neither needing to save up for a big day (Celebrity Net Worth claims Deschanel is worth $25 million and Jonathan $100 million) they still hadn't set a wedding date well over a year after Jonathan got down on one knee.

"Now we're so focused on the holidays that we're waiting. In the new year, we'll start thinking about what we want to do and how we want to do it," Jonathan told E! News in December 2023. Drew Scott then joked, "I just need to know if I'm planning the bachelor party, so I can get started," suggesting his brother and future sister-in-law hadn't even planned their pre-wedding celebrations. But, despite Jonathan claiming they'd start preparations soon, they were still no further along by November 2024. Jonathan told Us Weekly even he was frustrated by their lack of plans, admitting, "I'm actually sick and tired of myself not figuring it out yet. We haven't had any progress." Drew joked he needed to know his brother's wedding date soon so he could book a vacation, proving he wasn't the only one growing restless over their lack of organization.

In January 2014, more than five years before Zooey Deschanel and Jonathan Scott started dating, "Property Brothers" fans were hoping for a romance between her and Jonathan's twin brother. Awkward! Social media users got their hopes up after Drew Scott and the "Yes Man" actor chatted on X, formerly known as Twitter, with their messages seeming a little flirty. Deschanel posted her Elle cover and Drew jokingly responded, "That's the same wardrobe I was going to wear for a GQ cover! Great. now I have to change." That inspired one fan to tweet, "You know....I could totally see you with [Zooey], ask her out!"

Deschanel and Drew's public social media exchanges didn't end there. The following month, she posted a photo of herself and her stunt double Monica Braunger. Drew saw the snap and joked, "Monica..if you ever need a back up double for Zooey, I'm there for you," alongside a winking face and the hashtag #6foot4double. He got Deschanel's attention that time, as she responded, "That's a great idea, since we look so much alike!" Despite fans hoping for a romance though, their online banter was all platonic. Drew was dating his future wife Linda Phan and Deschanel started dating her future ex-husband Jacob Pechenik a few months later. Still, their interactions are pretty interesting considering she eventually found love with his brother.