A Look At Logan Paul's Dating History

Chances are even if you're not big into YouTubers, you still probably have heard of Logan Paul. The Ohio native began his career on the now-defunct app Vine, only to become a YouTube sensation thanks to the millions of subscribers to his channel where he would post daily vlogs about his life. Paul also dabbled in acting, with one of his latest roles in 2020's "Valley Girl." Yet he came dangerously close to ending his career in late 2017 after he uploaded a video on his trip to Japan that featured a man who had committed suicide in what is known as the country's infamous "suicide forest" — Aokigahara, at the base of Mount Fuji.

While the controversy was a setback, Paul apologized and eventually returned to vlogging. These days, it appears that he has most of his focus elsewhere. In 2018, he created his own podcast, "Impaulsive," and that same year, he also began his professional boxing career. Paul has since fought in several matches, including one against the legendary Floyd Mayweather Jr.

When Paul isn't making vlogs or podcasts, or preparing for fights, he seems to have no problem in the dating field. The YouTuber has been linked to several models and fellow YouTube stars over the years. And while he's never faked a marriage like his brother, Jake Paul, Logan Paul's romances have been juicy enough not only for YouTube content but also to grab some headlines. So let's break down the elder Paul's interesting and somewhat messy dating history.

Jessica Serfaty

Logan Paul's first high-profile relationship was back in 2014 when he dated model/actor Jessica Serfaty. According to Ranker, they dated for two years, reportedly making it the boxer's longest relationship yet, with the twosome even living together at one point. While the former couple mostly kept a low profile, which is very unlike Paul (you'll see), they did make some Vines and YouTube videos together that showed them kissing and cuddling, which definitely confirmed their couple status. 

Yet despite how happy they may have seemed online, the two allegedly had a bad breakup, with rumors that Serfaty may have even cheated. Some blogs also suggested that Serfaty had used Paul for fame. Fans have pointed out that following their split, Serfaty moved on to date other celebrities like Niall Horan, Justin Bieber, and Ed Westwick. In 2016, Serfaty's ex-husband, non-celebrity Ididia Serfaty, told the Daily Mail that the model had "abandoned" her son in Arkansas, adding, "It's hard not to think of yourself when you are trying to build a Hollywood career."

Whether that's all true or not, Serfaty did make a name for herself on "America's Next Top Model" and movies like "The Ride." While Serfaty and Paul never confirmed the reason they broke up, they both seem over it. Serfaty got engaged in 2019 to Firefly CEO Kaan Gunay. As for Paul, Serfaty wouldn't be the last girl he'd make videos with.

Amanda Cerny

It's safe to assume that Logan Paul's next relationship, with another former Vine star and YouTube personality Amanda Cerny, probably gave his video views a boost. That's because, when the two got together from 2016 to 2017, they basically allowed fans to watch their relationship unfold since they documented practically the whole thing for both of their YouTube channels, according to J-14.

From the jump, Cerny posted a video of their first date and would then upload videos with Paul with titles like "We Smashed," reportedly for clickbait. Paul also featured Cerny frequently on his channel with his own steamy titles like "Things Got Wild." Yet, despite all the juicy content, the two eventually called it quits, with reports that their relationship had fizzled, or maybe they just ran out of video ideas.

It appears their split really was drama-free though since the former couple remains friendly to this day. In 2021, Cerny posted photos of her and Paul where she expressed support for his boxing career. She wrote, "I'm so proud of how much you have grown as a human being ... how hard you work, how loyal you remain to your family/friends and for proving ... no matter how big your goals are, you can achieve them!" She even added, "Love you!" at the end of the caption. But, Cerny isn't holding out for Paul since she apparently moved on to fitness trainer, Johannes Bartl. As for Paul, it seemed he was far from ready to be tied down.

Teala Dunn

YouTuber Teala Dunn was never officially Logan Paul's girlfriend, but the two did spark some romance rumors in 2016 thanks to a slew of super flirty videos they did together. While their videos like "We Made a Baby!?" were probably just for clickbait, the two had undeniable chemistry. In 2018, two years after they were speculated to be dating, Dunn confirmed that they had "hooked up" and that she "actually liked him more than a friend."

Yet, the "Are We There Yet?" actor's feelings for Paul apparently ended up completely changing after he uploaded a video of a man hanging in Japan's infamous "suicide forest." Apparently, since Dunn was once linked to Paul, she felt the need to upload her own video of her reaction to the controversy where she said, "I was really disgusted to be honest ... I just feel like you have to be out of your mind to film a dead body and, like, laugh about it." She also went as far as to say that Paul had "lost touch with reality," adding, "No matter how famous you get ... your integrity and your respect should not change."

Dunn eventually moved on, or at least reportedly used Paul's younger brother, Jake Paul, for a 2018 YouTube video that showed them making out, which of course sparked some dating rumors of their own, according to J-14. However, that wouldn't be the only time the Paul brothers allegedly hooked up with the same girl, with the next one being much messier.

If you or anyone you know is having suicidal thoughts, please call the National Suicide Prevention Lifeline​ at​ 1-800-273-TALK (8255)​.

Alissa Violet

Logan Paul's 2017 romance with yet another fellow YouTuber, Alissa Violet, was quite complicated and somewhat icky. That's because Violet had dated Paul's younger brother, Jake Paul, and admitted to hooking up with Logan Paul as a form of revenge. Yes, it was quite the YouTube scandal when, in now-deleted tweets (via Seventeen), Jake wrote that Violet had cheated on him with someone "very close" to him and later revealed that Violet "f***ed my brother."

Violet confessed that she and Paul got together when she was upset that his younger brother didn't invite her on a weekend trip. She told Shane Dawson, "I hit up Logan and was like 'yo, let's hang out,' and then we all went to a club ... and then me and Logan hooked up." She added that, "she was disgusted by it." Yet, following their hookup, Violet did decide to join Logan Paul in his 2017 Jake Paul diss track, "The Second Verse," where he raps, "that's Alissa Violet, used to be your chick, now she's in the Logang and you know she on my team."

Violet would later claim that she had wanted to keep their rendezvous a secret, but it was Paul who blabbed, telling her (via Dexerto), "I'm a savage." It's unclear whether Paul and Violet actually ever liked each other or just used each other to get back at Jake Paul, but their time together will always be one of YouTube's juiciest scandals.

Ayla Woodruff

Logan Paul is no stranger to messiness, including when it comes to relationships, so it's no surprise that he may have mixed business with pleasure. In 2017, Paul was reportedly linked to his own personal assistant, Ayla Woodruff. A relationship between the two was never confirmed, but fans speculated that they were more than just friends/co-workers since Woodruff would frequently appear in Paul's vlogs. The two were apparently so flirtatious that fans even gave them the couple nickname "Layla."

Ultimately, if they were together, it didn't last long since in 2017 Paul rather harshly tweeted that Woodruff was no longer working for him by writing, "OY I REPLACED MY ASSISTANT WITH A NEWER, BETTER ASSISTANT GO WATCH NEW VLOG YEET." Of course, this led to rumors that something bad went down between Woodruff and Paul for him to fire her.

Woodruff decided to, of course, take to YouTube to explain that she actually left her job as Paul's assistant to create her own vlog. She also clarified that they were on good terms adding, "Logan and I still hang out, you guys still see me on the vlogs all the time." She continued, "It's no hard feelings. I'm super excited for him to have a new assistant and to get it straight, he will not admit this in the vlog, he did not fire me." Regardless, Paul clearly helped Woodruff's career, so it apparently was worth actually having to be his assistant.

Chloe Bennet

Logan Paul didn't just date vloggers; he also had a relationship with "Agents of S.H.I.E.L.D." star Chloe Bennet. The two first sparked dating rumors when they were caught kissing on a beach while on a break from filming their 2020 film "Valley Girl." In true Logan Paul style, the YouTuber couldn't help but vlog about their romance, telling fans, alongside Bennet, that they were "friends," adding, "When you have a crush on someone and you like them, and then a paparazzi pops you."

The two would eventually get more serious, with Bennet sticking by his side during his Japan "suicide forest" controversy. Paul revealed to The Hollywood Reporter that she had even warned him, saying, "'Yo, this behavior is going to bite you in the a**.'" Bennet also defended their relationship, tweeting that Paul is, "kind, creative, funny ... and he's one of my best friends" and "He's changed my life for the better and I've done the same for him."

While the couple didn't work out, Paul still holds Bennet in high regard. He told Entertainment Tonight in 2020, "That girl changed my life. I have so much love for her and I'm so blessed that I got to do that movie and spend time with her." He continued that she "became a light for me in a time where I did not have one. I carry on today in my life [the] values that she's instilled in me." Not a bad way to talk about an ex!

Corinna Kopf

Logan Paul's romance with Corinna Kopf in 2019 may have only been a brief fling, but it was enough to make for a good podcast. The two were an unlikely pairing from the beginning since only a year before they "hooked up," Kopf took issue with him after his controversial Japan "suicide forest" vlog. She called him out on Twitter, writing, "i'm truly sickened by this logan paul situation. i lost my brother to suicide ... my brother took his own life by hanging himself ... how insensitive and sick can you be to film someone in that state."

Kopf may have been hurt by Paul's actions, but she revealed on his podcast "Impaulsive" that she eventually decided to slide into his DMs after he pronounced her name wrong on his show, and the two ended up meeting "up in the middle of the night" to talk about the incident. Romance rumors began when Kopf and Paul were spotted wearing matching yellow sweatshirts and cuddling at a basketball game. Apparently, though, their time together was a bit complicated.

Kopf revealed that while they were hanging out, they didn't have sex until a year after they started dating because he wouldn't get an STD test. Paul, on the other hand, accused Kopf of complaining too much, and of being a hypochondriac and germaphobe. In the end, their romance may not have lasted long, but they were on good enough terms for Kopf to come on his podcast.

If you or anyone you know is having suicidal thoughts, please call the National Suicide Prevention Lifeline​ at​ 1-800-273-TALK (8255)​.

Josie Canseco

Logan Paul decided to go about his next relationship a bit differently, in that he admitted it was serious. In 2020, Paul dated model Josie Canseco after she ended her relationship with reality star Brody Jenner. Paul confirmed their relationship by telling Entertainment Tonight that they were quarantining together, adding that it happened after "We crossed circles one night ... It's f***ing serious. It's pretty serious."

While Canseco appeared in some of his vlogs, Paul also revealed that he wanted to keep his relationship with her more low-key due to his previous experiences with exes. He explained, "I'm hesitant to involve the person I'm spending my time with as much as I do everything else, for the sake of them and their life." Despite Paul's best efforts, he and Canseco didn't work out, which he revealed on his podcast "Impaulsive" by referring to her as his "ex-girlfriend." He admitted, "It's hard ... how do you tell the world it's over."

Canseco also opened up about their split on the "Between Good and Evil" podcast, revealing, "We just didn't necessarily see a future with what we had there at the time ... We just went through some s*** ... but we love each other and we're trying to find a respectable place." However, her dad, legendary baseball player Jose Canseco, decided to start a Twitter feud with him by tweeting he'd fight the Logan brothers. Josie was not pleased and dished, "He crossed a line ... embarrassing me calling out someone that I'm still very close with."

Alex Cooper

While Logan Paul was seriously dating Josie Canseco on and off between 2020 and 2021, he did find time in there to have a brief affair with "Call Her Daddy" host Alex Cooper. The whole thing was apparently supposed to stay a secret, but someone blabbed. Cooper broke it down on the "BFFs" podcast, revealing, "I hooked up with this guy and then Harry [Jowsey] tells me that he is running his mouth around L.A. ... telling people that we hooked up." She went on to dish that it was Paul, adding, "We weren't gonna tell anyone and Logan Paul is really bad at keeping a secret."

Paul responded to Cooper's claims on his podcast "Impaulsive," saying, "We hooked up and I was in a conversation with Harry Jowsey, a friend and I mentioned it to him ... and she construed it as I was running around town telling everyone." He clarified, "Alex is awesome, she's a great girl, we hung out, spent some time together," but when it came to their hookup, he "only told one close friend."

The two seemed to have since made up because Paul later appeared on Cooper's podcast where they reminisced about how they ran into each other post-hookup at a Vegas nightclub. Cooper joked (via Dexerto), that Paul "looked at me like you saw a f***ing ghost and started freaking out." It's good the two could move past the drama, especially since it made for good podcast content for them both.

Olivia O'Brien

As of 2021, Logan Paul's latest rumored girlfriend is singer/songwriter Olivia O'Brien. While they haven't officially confirmed their relationship, they both have definitely hinted that they're an item. First, O'Brien appeared on the "BFFs" podcast, where she admitted that she was in L.A. as "a member of the Logang," a term for Logan Paul fans. When asked if she was there to hook up with Paul, she answered, "Um, yeah, sure."

Then, while appearing on their friend Mike Majlak's YouTube channel, they inadvertently admitted they were dating after Majlak asked them if they were "getting travel fatigue for a new relationship." Paul and O'Brien went on to tell him about what seemed like a lovers' quarrel about Paul not remembering a "deep conversation" they had the night before.

While the two may currently be together, they also have quite the past. Distractify reports that the couple dated before Paul got with Josie Canseco, and at the time, O'Brien wrote a song about him. The singer dished on the "Zach Sang Show" that "Josslyn," a song about being with someone who still sees other people, was indeed about Paul but that she didn't want anyone to know. It seems that Paul and O'Brien at least have some unfinished business since they are clearly still hanging out. So is O'Brien "the one" or just another girl who makes for good content? Fans will just have to subscribe to find out.