The Stunning Transformation Of Jenna Sinatra

Jenna Sinatra has quickly become one of the most exciting Gen-Z content creators around. After launching a successful TikTok profile during the pandemic with her boyfriend, Will DeVane, Sinatra has expanded to YouTube, racking up millions of subscribers. The pair are now known for their relatable content, their down-to-earth personalities, and their adorable relationship. Sinatra is also known for being a dedicated Disney and Eagles fan.

As of 2023, Sinatra is 20 years old and is currently in college. She and DeVane are also in the middle of completing their plan of traveling to every state in America. In the future, the New Jersey native hopes to keep creating content and, maybe, to settle down in her home state with DeVane. So far, things seem to be on track — Sinatra is even signed to a talent agency, and she and DeVane's relationship is stronger than ever. 

There are, however, a few rumors going around as of December 2023 — some fans are convinced that Sinatra and DeVane have quietly broken up. But more on that later...  

Jenna Sinatra is a New Jersey girl through and through. Born on May 12, 2003, Sinatra was raised in, as she told Tubefilter, a "small town" in the Garden State with her older brother, Nick Sinatra, who she seems to be incredibly close to. In 2018, she posted a picture on Instagram with her family at one of his football games, writing, "Very proud." Then, in 2019, when her brother graduated from high school, she wrote, "Love you bro." In 2021, she posted a longer tribute to Nick on his birthday. "I cherish our rare 3 am talks more than you think," she wrote. "I look up to you and admire your attitude so much. Thanks for being such a bright light in my life and of course for always making me laugh."

As it turns out, Jenna Sinatra's future boyfriend, Will DeVane, was best friends with her brother. As Jenna later wrote on Instagram in 2020 about DeVane, "You went from playing on my lawn with my big brother when you were 10 years old to being my whole world."

Even though Jenna Sinatra had grown up with Will DeVane playing on her lawn with her big brother, Nick Sinatra, it wasn't until she and DeVane were both in high school that they became close. Jenna started high school in 2017 — as she revealed in her graduation post four years ago. She attended Southern Regional High School, which is located in Manahawkin, New Jersey. According to Tubefilter, "We never really interacted until high school." 

About halfway through high school, Jenna Sinatra and Will DeVane started dating. In May 2019, she and DeVane went to junior prom together. Then, they had their first official date on June 2, 2019. By September 2019, she was cheering DeVane on in his football games. "Your touchdown counted to me," she wrote, with a heart emoji, in a September post, and, "My senior," she wrote in an October post, standing with DeVane after a football game.

During the pandemic, when Jenna Sinatra and her boyfriend Will DeVane were still in high school, the pair began to think about creating some digital content. "We got the idea during the pandemic," Sinatra explained to Tubefilter in 2022. At first, it was just a way to pass the time and have some fun. "We were really bored and we just started making silly challenges. And then we started getting comments like, 'Oh, I want to be in a couple like this.'" That's when they realized that they might be onto something. "We just started doing more and more," she said.

In another interview with Tubefilter, DeVane explained that he and Sinatra were both very new to social media when they began. "I would say that we are a young couple that kind of just came out of nowhere with social media and we both never did any type of social media before we started," he said. "We just started putting ourselves out there and being ourselves online and people really loved that — and our relationship was a very relatable thing."

As her popularity grew, Sinatra also started putting fitness content onto a new TikTok channel, @jennasfitness, in 2020. There, she posted videos about her runs and her other fitness routines.

After Jenna Sinatra and her boyfriend Will DeVane began making content for TikTok, they had their first hit with a video about running with your boyfriend. 

"I finally convinced Will into it, and he made this video of what it was like on a run," Sinatra told Tubefilter in 2022. "So it was us going on a run together, and it was him three laps in and I was still on my first lap." Very relatable content if you ask us! And clearly, their audience agreed. "It took off and we were so shocked," she said.

The couple even made a "Part 2" to the video because it was so popular. In a 2020 video titled, "Don't run with your girlfriend!!" DeVane films as Sinatra runs alongside him in a field. In words added on top of the video, he wrote, "Decided to go on a run with my girlfriend. She was struggling at first. Turns out she's just slow as f***." We then see Sinatra struggling to catch her breath.

After getting her start on TikTok alongside her boyfriend Will DeVane, Jenna Sinatra decided to start uploading video content onto YouTube, too. They decided to expand after people commented asking them to make YouTube videos. "We were like, 'I don't know if we're made for that,'" Sinatra said to Tubefilter. "But then we figured, let's do it. We've always looked up to people on YouTube growing up, so we were like, let's try it."

For Sinatra, moving to YouTube was a little intimidating. "YouTube is so stressful because you have to really understand the short-form and the long-form," she said. "And you get to see someone's personality."

However, even though she was a little nervous, their YouTube channel proved to be extremely successful — in fact, they were getting 440,000 views in their first month of doing YouTube Shorts alone. Eventually, Sinatra found that their fans on YouTube were even more invested than on TikTok. "We just love the connections we have with our supporters," she said.

Jenna Sinatra graduated from high school in 2021 — naturally, Will DeVane was her prom date, even though he had graduated a year earlier. The pair both began college — even though they both hoped to become full-time content creators. "We are going to school to get our degrees to have as a backup option," she said to Tubefilter, adding that their parents would've killed them if they hadn't. 

Sinatra's degree might help her in her future career. Although she began her degree majoring in education, that soon changed. "I'm majoring in communications with a minor in creator and production," she said to Tubefilter in October 2022. As Sinatra told her followers on YouTube, switching her major helped, but she still doesn't love going to college. "I switched my major ... I don't really love school," she admitted. 

Sinatra and DeVane made an effort to balance their college work with their digital content creation. They both made an effort to schedule their classes in the morning — "So we have our time together for social for the afternoon," she said in April 2022. "That's kinda how we found time."

Jenna Sinatra was brand new to social media when she started making TikTok videos. She and her boyfriend, Will DeVane, have learned a lot since starting their channel in 2020. "We've learned so many things being on TikTok," she said to Tubefilter in April 2022. "We never really had any knowledge in this aspect of social media, and we've just learned so much. We love it." Looking back at their content over the years, it's clear that she and DeVane have become masters of both TikTok and YouTube.

While Sinatra may have been new to social media, she wasn't completely new to creating videos. "I was actually in a TV production class in high school, and I learned there," she said of her editing skills. "So I was very lucky I took that class. And I have learned and grown more since we started."

These days, to become a successful content creator on social media, you sometimes need a little help from professionals in the industry — and that's exactly what Jenna Sinatra and her boyfriend Will DeVane did. In 2021, the pair began working with The Network Effect, a company that offers guidance to content creators on creating effective short-form video content. "They've helped us so much with different content mixes and diversified us across all platforms," said Sinatra to Tubefilter.

In 2023, Sinatra also signed with Outshine Talent, a talent agency for content creators. "We are thrilled to welcome @jenna.sinatra to our #OutshineTalent fam!" the agency wrote on Instagram at the time. According to DeVane's Instagram profile, he also signed with the agency.

Sinatra and DeVane are continually looking for ways to expand and grow — and sometimes, that has meant working with agents and advisors. Whatever they're doing, it's working.

For Jenna Sinatra, she has met milestone after milestone in the past few years of her career as an online content creator. In 2022, she hit another big one — one million subscribers on her joint YouTube channel with her boyfriend, Will DeVane.

For Sinatra, reaching the milestone was a huge moment. "It's actually insane," she confessed to Tubefilter. As she explained, they had never really been aiming for so many followers. "When we started, we never thought we would hit a milestone like that. We thought we would probably just keep riding at lower numbers. We never thought one million would be a number that we'd even consider reachable in two years."

As of 2023, the pair already have 1.34 million subscribers — clearly, their numbers are still rising — and fast! And we have to say, they deserve their success.

Jenna Sinatra may have found success with social media, but that doesn't mean she wants to leave behind her small town for the big city. In fact, in a YouTube Q&A in 2023, she explained that she hopes to stay in New Jersey for the foreseeable future. As she explained, she likes the fact that New Jersey has four distinct seasons. "I like New Jersey, and I think I want to be here for the rest of my life," she said while speaking to her followers from the car with her boyfriend, Will DeVane. "But I also want a place somewhere else." 

DeVane chimed in asking if what she meant was that she wanted multiple homes in New Jersey and elsewhere in the country. "That's not easy to do," he said. She replied confidently, "Oh, I know it's not easy to do, but my expectations — I'm gonna [be] to able to do that." The pair then sealed the deal with a fist bump — these two are couple goals. 

In 2023, Jenna Sinatra and her boyfriend Will DeVane embarked on a new challenge: Traveling to each state in America. "We're trying to travel to a different state in the U.S. for each month," Sinatra told Tubefilter at the end of 2022. "So that is still our plan." She added, "It's definitely something we've always wanted to do, traveling."

The pair began the challenge in early 2023, throwing a dart on a map to determine their first destination. DeVane then blindfolded himself and threw his dart at the map, landing on Michigan. The pair set off for Detroit where they went skating, wall climbing, played mini ice hockey, and went to a hockey game. For their second destination, they landed in Florida. The pair traveled to Key West, Florida in February 2023. For their third state, they traveled to Pennsylvania — they ended up traveling to the Poconos. 

However, as of December 2023, the pair haven't visited another state — either the project simply became too much work, or there's something more scandalous going on. Some fans believe that the pair have actually broken up. It doesn't help that they haven't posted any videos or images together in months.

In 2023, Jenna Sinatra faced one of her biggest fears — flying alone. Although the young content creator had flown with her family and her boyfriend in the past, it was the first time she had ever been on a plane by herself, traveling to spend the week with her mom and friends.

"I am flying for my first time by myself ever in my entire life and I am so freaking stressed," she said in a video. "If you guys know me, I am the most anxious person probably ever especially when it comes to traveling." She went on to explain that she never thought she'd be able to fly alone, but she was finally doing it. 

Although Sinatra felt more and more anxious as the day went on, it looked like her trip was a success. Sinatra beeped out the location she was traveling to, but based on her Instagram, it looks like she was traveling to Disney World in Florida. And she had a great time!

So, what does the future hold for Jenna Sinatra? Well, as she told Tubefilter in 2022, she hopes to keep making content and to one day make enough money for it to be her full-time career. However, she knows just how risky that career path is. "Our main priority would definitely be doing what we do now for our future, but we know that it's not something that's guaranteed, and it can end at whatever time," she said. 

As of 2023, Sinatra is already well on her way to making her dreams a reality. She has 2.1 million followers on TikTok and, with her boyfriend Will DeVane, 1.34 million on YouTube. On Instagram, she's up to 189,000 followers. In fact, according to WikiFeed, she already has a net worth of $1.5 million. At this rate, we'd say she has a pretty good chance of making a career out of social media!

What else lies in Jenna Sinatra's future aside from her YouTube and TikTok success? Well, she and her boyfriend Will DeVane have a few plans. First, DeVane wants to move into his own place — with Sinatra, of course! "You want to get a house with me?" Sinatra squealed as DeVane revealed his plans during a Q&A.

Sinatra then read out a question about whether or not the pair had plans to get engaged in the future. Although DeVane and Sinatra both declined to answer, their smiles said it all: Both seem like they hope to get married one day in the future. The pair then answered a question about whether or not they planned on having kids. "We were talking about this the other day," said DeVane as Sinatra grinned. "We feel like every couple or everyone is just getting pregnant but us." It sounds like these two certainly have a lot of plans for the future — and we can't wait to see what they do next.