January 2020: Happy New Year...
Dobrev and White hit it off after they partied together with friends, including her Vampire Diaries co-stars Kayla Ewell and Candice Accola King, at the opening of the Bellagio Resort & Casino's new supper club The Mayfair in Las Vegas on New Year's Eve.
A year later, amid the coronavirus pandemic, Dobrev would share this photo of her and White at the bash, as well as a video of him lifting her up Dirty Dancing-style only to have them both topple into the snow. She wrote, "How we thought 2020 would go...how it actually went."
March 2020: Romantic Bike Ride
Dobrev and White spark romance rumors after they are spotted riding bikes together in Malibu, Calif. A source tells E! News that the two began to "ease into a relationship" after spending New Year's Eve together, adding that things "really accelerated" between the two after the coronavirus pandemic broke out.
"After spending weeks together during quarantine," the source says, "Nina and Shaun have made it clear to their friends that they are a serious couple."
May 2020: Snip Snip
The two make their relationship Instagram official when both share a photo of the actress trimming White's red hair. Most hair salons closed due to COVID-19 restrictions. Under her post, Dobrev writes, "Adding to resume: hairdresser."
November 2020: Happy Thanksgiving
Dobrev and White celebrate Thanksgiving with his family, as seen in photos he posts on Instagram.
December 2020: Road Trip!
Judging from their Instagrams, Dobrev and White vacationed together in the Zion National Park area in Utah twice in 2020, in May and in December.
December 2020: Happy Holidays
The two spend the holidays together in December 2020.
December 2020: "So In Love"
Just before New Year's Eve, another source tells E! News that the two "are genuinely so in love."
"They openly talk about their future together," the insider continued. "They're just super happy, and things are going really well with them."
January 2021: Happy Birthday, Nina... Again!
Dobrev celebrated a "redo" of her 31st birthday on her 32rd and White paid tribute to her with photos of the two sporting these looks.
October 2021: Check Mate
Alonside pal Adam DeVine, the couple dressed up as characters from The Queen's Gambit for Halloween with White going as as the iconic Beth Harmon and Dobrev channelling U.S. chess champion, Benny Watts.
January 2022: Snow Bunnies
Dobrev hit the slopes with her pro snowboarder love at Copper Mountain in Colorado.
February 2022: Last Olympics
After White finished fourth in the Men's Snowboard Halfpipe at the 2022 Olympics and officially retired from competing, Dobrev expressed how proud she was of him.
"The end of one chapter, means the beginning of an exciting new one with endless possibilities," she wrote in part of an Instagram post. "You will forever be the G.O.A.T. of snowboarding. Not to mention you are also the G.(B).O.A.T. = Greatest Boyfriend Of All Time."
May 2022: Red Carpet Debut
The couple finally went red carpet official at the Top Gun: Maverick film premiere in London.
May 2022: Red Hot Romance
Alongside her tux-clad boyfriend, Dobrev sizzled in a red Monot gown at the 28th annual amfAR Gala during the 75th Cannes Film Festival.
May 2022: Hearts Racing
The pair watched the qualifying for the F1 Grand Prix of Monaco ahead of the big race. For the occasion, Dobrev looked wore a chic, chalk-colored suit by Smythe.
June 2022: Fun in the Sun
The two turned up the heat while vacationing in the Maldives.
September 2022: Birthday Boy
"I really picked a winner [ and he really picked a booger ]," Dobrev wrote in an Instagram tribute for White's 36th birthday. "Happy belated Birthday you weirdo. My weirdo. @shaunwhite."
October 2022: Degrassi Days
What did White really think of Dobrev's cheerleading scene from Degrassi: The Next Generation? The athlete gave his reaction on TikTok and proved once again they're always on each other's squads.
December 2022: Family Time
The duo celebrated the holidays with a family trip to Mexico.
January 2023: An Out-of-This-World Tribute
"What planet are you from and will you take me with you?!" White wrote on Instagram for Dobrev's 34th birthday during their trip to Antarctica. "Thanks for making life incredible! Happy birthday my love."
February 2023: Valentine's Day
"Life is a roller coaster with you," the actress wrote on Valentine's Day 2023. "It goes from serious to baby birding in seconds … thank you for always making me smile. happy valentine’s day @shaunwhite."
January 2024: Sweet Shout-Out
"Life with you has been my greatest adventure!!" White wrote on Instagram for Dobrev's 35th birthday. "Happy birthday my love!!"
March 2024: Oscars Night
The duo looked so sharp at the 2024 Vanity Fair Oscar Party they deserve their own trophy.
July 2024: Happy Independence Day
The two celebrated the Fourth of July with several celebrity friends, including Miles Teller and Keleigh Teller and Usher.
October 2024: Engaged
Shaun and Nina announced their engagement Oct. 30, 2024. A week later, they walked their first red carpet as an engaged couple, at the 2024 Earthshot Prize Awards in Cape Town, South Africa.