Chris Olsen Breaks Down ‘Intense’ First Date with Boyfriend Harrison Dockerty

Social media influencer Chris Olsen has confirmed his relationship with British real estate analyst Harrison Dockerty, sharing insights about their connection during a recent podcast appearance. The couple’s journey, which Olsen detailed on Jamie Laing’s “Great Company,” offers a glimpse into their romance that blossomed over the last year.

Olsen first began hinting at his new relationship in mid-October, when he posted several TikTok videos featuring Dockerty, albeit with his face obscured. This led to speculation among fans until December 22, when Olsen made a formal announcement on TikTok, showcasing his efforts to surprise Dockerty with roses after travelling to the UK.

In the podcast aired on February 25, Olsen recounts how he met Dockerty last summer in London, shortly after taking a break from social media. Ready to reenter the dating scene, he asked his therapist for guidance, who encouraged him to go on a few dates. Following her advice, he scheduled five dates within a single week. Reflecting on his experiences, Olsen noted that while some dates were enjoyable, others left him feeling disheartened. Dockerty, who turned out to be the final date of that week, piqued Olsen’s interest right away.

Olsen was initially drawn to Dockerty’s dating app profile, which revealed that he was an opera singer. Intrigued, he messaged Dockerty, playfully asking, “How many dates until you sing for me?” Dockerty’s response set a light-hearted tone for their budding relationship, suggesting a performance after three dates.

Their first date, however, took an unexpected turn when Dockerty chose to take Olsen to a Hyrox workout class—a high-intensity competition-based fitness session that left Olsen feeling overwhelmed. “I show up, and I almost die,” he joked about the experience. Despite the physical challenge, the two enjoyed a post-workout pizza outing where they talked for five hours, marking the beginning of a close bond between them.

As their relationship progressed, Olsen described their dynamic as a “slow burn,” influenced in part by cultural differences in expressing affection. He noted that Dockerty’s reserved nature led both to assume the other was less invested in the relationship. Reflecting on their mutual feelings, Olsen expressed how he initially enjoyed the possibility of something more, while believing Dockerty might not share the same sentiment.

Delving deeper into their relationship, Olsen shared that he felt secure in his own happiness prior to meeting Dockerty, stating, “I had been happy alone for a while.” His self-assurance contributed to a sense of stability in their partnership, which he described as a supportive endeavour rather than a means of filling emotional gaps. Dockerty, he explained, supports him, and together they navigate life’s challenges.

Professionally, Harrison Dockerty, a graduate of the University of St Andrews, has been contributing to the real estate sector for the past three years as a fund analyst at Knight Frank, a prominent real estate consultancy based in London. Olsen’s decision to initially obscure Dockerty’s identity on social media stemmed from a desire to maintain a level of privacy in their relationship. He expressed his intention not to turn his online presence into a “couple account” again, highlighting the importance of enjoying their romance away from public scrutiny.

Chris Olsen first rose to fame in 2020 through content that chronicled his life during lockdown with former boyfriend Ian Paget. Following their breakup in 2022, Olsen reassured his audience that he would adopt a more private approach to his romantic life, acknowledging the complexities of relationships made even more challenging by external opinions.

As their relationship develops, Olsen and Dockerty appear to value their privacy and commitment to each other, igniting feelings of affection and support as they embark on their journey together. Through candid discussions and shared experiences, the couple embraces the unique challenges and joys that their relationship brings, making it one filled with promise and growth.