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Oliver James Montgomery-Why Chris Olsen and Meghan Trainor's Friendship Is "Much Deeper Than a Working Relationship"
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Date:2025-04-10 14:18:12
When it comes to his friendship with Meghan Trainor,Oliver James Montgomery Chris Olsen isn't lyin', lyin', lyin' about how close they are.
The singer, 29, and the social media star, 25, have become a fixture on TikTok For You Pages, rocking out to her hit "Made You Look" and hanging out with her husband Daryl Sabara and 2-year-old son Riley.
Still, fans' lips are movin' and speculating that Chris was hired by Meghan to help her with her TikTok. And now, he's offering some clarity on the rumors.
"We became friends before all of this, before there were any suspicions or before we ever started working with each other and stuff like that," Chris told E! News in an exclusive interview. "It's all based on this real friendship that we have."
It's not like Meghan and Chris have totally shied away from the topic. She brought it up on a June episode of her podcast Workin' On It—telling listeners, "We paid him. We're like, 'Please be on the team.' He's on the payroll." Chris even joked in a recent video about Meghan renewing his contract "so we can be friends again."
But ultimately, Chris says, their bond grew organically. "We did the podcast together, and then we made some TikToks, and then we were like, 'Should we continue doing this, making TikToks together?'" he continued. "And you know, she wanted us to kind of work together in that way rather than just have it be this one-time thing."
Still, Chris is confident they'd be joined at the hip even if they hadn't had these work discussions.
"I think regardless of if we ever had the conversation of working together, we still would be hanging out the way that we do," he added. "I truly love her. I've gone on vacation with her family now, and we're about to go on another vacation together. So, it's definitely much deeper than a working relationship."
And whether it's for work or play, they enjoy spending time together.
"But we also have a lot of fun making TikToks together," Chris noted. "Promoting 'Made You Look' when that whole thing started and when she had finished the song and decided to put it out into the world was such a fun thing to do together as well. So yeah, we're friends first, and I love her, and I love her family, and I love Riley—who's the cutest kid ever—and I can't wait for the next kid to come as well."
Meghan announced in January that she and Daryl are expecting their second child together, telling E! News how Chris supported her through what was a difficult first trimester as days of bleeding had her worried she was experiencing a chemical pregnancy.
"She shared that she thought she was pregnant and then we thought she may not be," he recalled. "It wasn't like a moment where it was just like, 'I'm pregnant' and you're really excited. There was a lot of question marks around it. But then when we actually found out and it was something that she was pretty confident about, then it was really exciting."
Through it all, Chris offered Meghan a shoulder to lean on. "I was just there for her no matter what," he shared. "I was like, 'Whether or not another baby is coming, we're going to be OK. Good things are going to come no matter what.' I'm so excited for her and Daryl because I know they really wanted this, and I think Riley's going to be the best big brother ever."
Support is what Chris and Meghan have given each other ever since they first connected on social media and shared their first video together last April. (So no, as he confirmed to Entertainment Tonight, they haven't known each other since childhood).
"It's funny because people have said to me, 'Ever since you and Meghan started hanging out, she's gotten so funny.' And I'm like, 'No, no, no, no. She has always been so funny,'" he told E! News. "I think just now she's showing it on the app, and we're sharing ourselves with the world in a different way. I think that's where I always land whenever I'm talking about TikTok with people is if you share yourself in a way that you feel happy about and a way that you feel comfortable with, then you can only win. As long as you're being authentic, then people are going to receive that in the way that they do and there's no one better at being you than you."
Chris said Meghan has taught him a few things about social media, too—like how to deal with any haters.
"There are times that I still struggle with reading comments or seeing negative things on the internet about myself, and she's been really helpful in those moments," he said. "She's been on the receiving end of that a lot too, and that doesn't define you as long as you're being authentic to yourself. And I think hearing stuff like that from her—from someone who knows and has been in this industry for so long—is really helpful because I know she's speaking from her own experience."
Give them that title, title: BFFs.
Meghan isn't the only celebrity Chris knows. In fact, he's rubbed elbows with quite a few stars—including JoJo Siwa, Ashley Tisdale and Austin Butler—through his viral coffee delivery videos on TikTok. And now, the content creator has his very own coffee brand, Flight Fuel, consisting of bean blends, cold brew concentrates and accessories.
"It's been two years of doing this little bit," Chris said about the series. "And so, a year into it—when I realized that it was still something that people loved watching and that was really becoming a part of my brand on TikTok—I was like, I want there to be a way that more people can be a part of this. People kept saying like, 'Can you deliver coffee to your fans? I would love that.' And while I can't deliver it to every single fan, I felt like this would be a perfect way to kind of help bring people into the bit and have people be a part of it."
As for a star who's still on his dream coffee delivery list? "Everyone in my comments section wants me to be able to somehow deliver to Harry Styles at some point, and I would love to do that too," he said. "And so I just keep that dream open. You know, nothing's impossible."
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