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In an emotional Instagram post on December 31, the 28-year-old influencer looked back on 2025, a year he described as "one of the hardest," especially following the death of his grandmother in September.
"When Lola and I made all of our videos together, I knew that eventually I would be glad I had them to look back on, but I thought we'd have time to make so many more," he shared. "I am grateful for the fact that the last time we saw each other before she was in the hospital was at one of my shows, where I pointed her out and made sure everyone cheered for her."
Despite the grief, Olsen highlighted positive developments in his life over the past months, including the start of his relationship with London-based real estate analyst Harrison Dockerty.
"I met my Harry who I have the biggest crush on," he wrote. "I have a clear path of what I want moving forward with my life, and for the first time in a while, I have hope that it will all happen. I know an outlook like this can always come and go, but I will hold onto it as long as I can because that's all Lola would want."
Olsen initially teased his relationship on October 17 with a TikTok post that blurred his boyfriend's face. He explained in the caption that he was choosing to be more private this time, writing, "I'm not tryna be a couple account again and for once I'm being more private & that's nice. I knowww the censor is annoyingggg but I still want to make these kinds of vids bc I am vvvv happyyyyy."
In the following months, he continued to share glimpses of their relationship on social media, including their couples' Halloween costumes, travels across Europe, and a lip-sync trend video, while keeping Dockerty's identity hidden.
Olsen gave rare comments about his boyfriend at the New York City premiere of Wicked: For Good in November, revealing that both he and Dockerty admire PEOPLE's 2025 Sexiest Man Alive, Jonathan Bailey.
On December 22, Olsen officially introduced Dockerty on Instagram with a romantic video, captioned, "finally found him," showing the pair traveling across a bridge with a flower bouquet.
Olsen has previously shared a public relationship with content creator Ian Paget in 2020, which ended in January 2022. Since then, he has been more selective about documenting his personal life online. Reflecting on his growth, he told PEOPLE that after a public breakdown in 2024, he decided to change his approach to social media, focusing on authenticity and prioritizing his well-being.
