JoJo & Dexter Darden’s Relationship Timeline Is Full Of Intimate Instagram Photos

The singer announced her engagement to the Maze Runner star on Christmas Day.

Singer JoJo and actor Dexter Darden
Amy Sussman/Alberto E. Rodriguez/Getty Images Entertainment/Getty Images

JoJo will not be telling her man to “Leave (Get Out)” anytime soon. The “Too Little, Too Late” singer is engaged to actor Dexter Darden, and they announced their engagement in a joint Instagram post on Christmas Day. “Forever with YOU? Sign me UP,” JoJo captioned the post. “Celebrating Christmas a whole fiancé!!! the most thoughtful, creative, positive, handsome, strong, loving, uplifting human being asked me to marry him. so obviously I said YESSS!!!”

Many fans were caught by surprise, having no clue that JoJo even had a man. While it’s not known how long JoJo and Darden have been an item, the couple reportedly started dating in the summer of 2020, as hinted in an Instagram post from June 2020. After that, they kept silent about their relationship for more than a year, with the Maze Runner star even gushing about his girlfriend on Instagram without hinting at her identity.

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When the singer’s mixtape trying not to think about it dropped in October 2021, Darden made it known how supportive he was of her, finally confirming what some eagle-eyed fans had suspected. After that, the couple has been vocally supportive of each other on social media, culminating with the news of their Christmas engagement.

Here is JoJo and Dexter Darden’s full relationship timeline, so far.

June 2020: Dexter Appears On JoJo’s Instagram

The first sign of JoJo and Darden’s romance popped up in June 2020, according to US Weekly, when Darden appeared on JoJo’s Instagram page to read a poem about racial injustice amid Black Lives Matter protests of the killings of George Floyd and Breonna Taylor. However, the evidence has since been deleted, given that the singer wiped out her Instagram page prior to August 2021.

July 2021: Dexter Hints At His Girlfriend

Darden made it clear that he officially had a new flame in summer 2021 — by posting a selfie of himself, on a dinner date, where JoJo’s hand can be seen lurking in the corner. “She caught me by surprise I must say,” he wrote. “Because I never have seen such a pretty face. With such a warm and beautiful smile, It wasn’t hard for me to notice her style.”

October 2021: Dexter Praises JoJo’s Music

On Oct. 1, Darden took to Instagram to praise JoJo’s newest project trying not to think about it, calling her “the bravest artist I know” and commending the singer for being so open about her mental health through music. “Trying Not To Think About It is a project that is Vulnerable, Honest, Motivational, Emotional, and most importantly True!” he captioned a photo of them lovingly hugging each other on a street corner. “So many people Battle with their Brain, and are afraid to express when they feel like they’re losing this battle. You guys are NOT ALONE! @iamjojo thank you for not only creating a Piece of Art, but for also encouraging others to talk about the state of their mental health!”

While he did not explicitly refer to his romance with JoJo, Darden made it clear that he was devoted to her and only her: “I’m so grateful I got to support you through this thing from beginning to end!!!”

November 2021: Celebrating Thanksgiving

JoJo made it Instagram-official with Darden on Nov. 26, sharing a slideshow of their Thanksgiving celebrations with her and Darden’s extended families. “happy THANKS DAY from our families to yours,” she captioned the post, which was led by a sweet snapshot of Darden kissing her cheek.

December 2021: JoJo & Dexter Get Engaged

Just days before their engagement, Darden paid tribute to JoJo on her 31st birthday, sharing a slideshow of memories from their relationship. “Happy Birthday To the Brightest Star In My Universe, The Beat To My Heart, The Woman I prayed for @iamjojo!” he wrote. “Jo Thank you for challenging me, Pushing me to be the best Man I can be, and Making me smile when no one else can. You are Gift from God to the world, and the best present I’ve ever received. TO THE MOON AND BACK, I got Your back!” JoJo gave him love back in the comments, writing, “ILY BABY, thank u for always going above and beyond for me/ us.”

On Christmas, the couple announced their engagement with a slideshow from their intimate proposal, including the obligatory ring picture. Darden got down on one knee during a trip to Puerto Rico at the La Concha Resort, where both of their mothers and best friends were waiting after the proposal. “Thank you for the most epic birthday surprise ever,” she wrote. “And for flying out my mom, your mom, and both of our best friends to share in that incredible moment with us. you are one of one. LFG @dexterdarden.” The actor responded in JoJo’s comments section, writing, “Yupppppp thank you for being my forever,” complete with ring and heart emojis.

February 2022: Super Bowl

Some couples just go to dinner or buy flowers for Valentine’s Day, but not JoJo and Darden. One day before the holiday, the pair attended the 2022 Super Bowl together. Darden shared several pictures of them at the game in what appears to be a box, captioning it, “Got to take my Valentine on a date yesterday! She wanted soup in a bread bowl, but instead We went to see some friends in one of the illest concerts since Covid, and I got to watch a football game🏈! Happy Valentine’s Day to The One who makes my heart Sing! . I Love you Baby!”