Bailee Madison's Complete Relationship History

Fans of celebrities likely find it hard not to be curious about their day-to-day lives. Specifically, celebrities' romantic relationships are something that people will always want to know more about. Actor and singer Bailee Madison has been dominating the entertainment industry since she was a child, starring in projects like "Bridge to Terabithia" and the Hallmark series "Good Witch." While her relationship history is on the shorter side compared to her work resume, it's full of fellow a bit of heartbreak and drama.

The talented star has gained many fans of all ages, so it makes sense that her relationships have garnered attention over the years. Madison also has been pretty vocal about her dating life over the years, finding love with other singers and influencers. At the time, she acknowledged that her partners had sparked happiness and inspiration in her life. However, she has kept quiet on many details about the reason behind any of her sad breakups. Nonetheless, the actor still appears to be a hopeful romantic!

Emery Kelly was Madison's first boyfriend

"Forever In Your Mind" singer Emery Kelly was Bailee Madison's first relationship in the public eye.The pair confirmed that they were dating in August 2015, when Madison posted a picture of the two of them together on Instagram with the caption, "One month of smiles with him." Fans were happy for the "Good Witch" actor, but it wasn't meant to be, as the couple broke up a few months later. No reason was given for the split, but in February 2016, Madison opened up to Clover Letter (via J-14) about some issues that took place in her first relationship, presumably about Kelly.

While she didn't mention his name in this instance, the actor referred to one comment her first boyfriend had made about her. "The person who called me a prude was the first relationship I'd ever been in," Madison revealed. "I honestly didn't even know what that word meant; I had to look it up online."

Madison also discussed her relationship and the fallout from her breakup with Kelly in a 2016 interview with (via Just Jared Jr). "I realized recently if a guy goes out and shares an opinion, he's applauded, and then when girls do it, they're over-sharing," the actor shared. She also admitted that, since this was her first public boyfriend and split, it made it even harder to get over. She learned to ignore the chatter online and focus on herself after this public breakup.

Madison dated Alex Lange for two years

Bailee Madison's second relationship was with social media influencer and YouTube personality Alex Lange. The couple started dating in 2016, and Madison talked about how they met during a March 2018 interview alongside Lange with Raw Magazine (via J-14). "I designed a T-shirt with two of my pals and I flew out for a store launch opening," she recalled. "He was friends with a couple of my mutual friends, he walked in and I turned to a couple of my friends and asked who that was. Then he positioned himself next to me and we just talked all night. I wanted to get his number but I didn't have the guts to ask, so I made my friends put me in a group chat with him."

The actor also opened up about their relationship on her podcast, "Just Between Us." She remembered how she would stay up until all hours of the night talking and texting with Lange when they were in the early stages of their relationship. 

While it seemed as if Madison and Lange were perfect for each other — he even admitted on her podcast that he told her he loved her the first night they met — news of their breakup surfaced in early 2019 after two years together. Neither party ever revealed why they split. Madison and Lange also haven't publicly spoken about each other since, so it seems as if fans will never know what went wrong.

Blake Richardson stole Madison's heart

Bailee Madison's third relationship is with New Hope Club's lead singer, Blake Richardson. The couple's relationship was publicly confirmed in 2019 when Madison posted a picture of the two of them on her Instagram looking annoyed, with the caption, "When they ask you to confirm it." 

Since then, Madison and Richardson have been as happy as can be, as Madison clearly showed in her Instagram post for Richardson's birthday on October 2, 2023. "24. Happy happy birthday @newhopeblake. The most excited for you and for this next chapter of life. Wishing you endless love and happiness always. I love you! (Ps. We've spent 5 birthdays together that's kind of fun)," the actor wrote.

Richardson and Madison also collaborated to write Madison's first single, "Kinda Fun" in January 2024. In an interview with People, Madison opened up about working with Richardson while also honing her own songwriting skills. After a songwriting session complete with wine, she said, "We went to sleep and woke up and we were like, 'Let's see if we still like it, or maybe I just had one too many glasses of white wine.' Then I listened to it and we were like, 'It just felt really honest and it felt truthful.'"