A Reminder That Pete Davidson’s Dating History Is Far From Bupkis

A Reminder That Pete Davidson's Dating History Is Far From Bupkis

As a seasoned observer of the ever-evolving world of celebrity relationships, I must say that Pete Davidson’s love life is nothing short of a rollercoaster ride! From brief flings to long-term relationships, he seems to be constantly navigating the ups and downs of romance.


Pete Davidson most recently made headlines for parting ways with a number of his tattoos.

Given that the former Saturday Night Live cast member had been soaked in a considerable amount of ink, as a symbol of his passionate relationships at times when creativity hit him, there’s no question that the process was physically challenging.

As a lifestyle expert, I’d put it this way: Years ago, just like many of us seeking change, Davidson expressed his desire to remove his tattoos by the time he turned 30. He shared that spending countless hours in makeup to conceal them for roles that didn’t match his signature look had become tiresome – a challenge that seemed to dominate most of his projects.

Despite not indicating a intention to halt dating, it seems clear that the period where the celebrity known as “Bupkis” was inscribing emotional messages on his arms has come to an end, based on his recent tattoo-free arm displays.

As I turn 31 this November 16th, it’s impossible not to find myself reflecting on my personal relationships, which have left quite an impression in the minds of many.

In the spring of 2023, I shared on Jon Bernthal’s Real Ones podcast that I’ve had romantic relationships during my twenties. Some find this fact intriguing, even bizarre. But truthfully, I don’t see what makes it so captivating.

It’s his belief, unfortunately, he found himself in a relationship with Ariana Grande when his fame was growing rapidly. Although their paths didn’t lead them to a lasting union, his charm has since proven to be indisputable.

A Reminder That Pete Davidson's Dating History Is Far From Bupkis

Davidson mentioned that he usually encountered many of his major romantic partners through work, referring to SNL as one of the five primary centers of Hollywood’s film industry, where you might run into virtually anyone on a typical day. This was simply due to who he was working with and spending time around.

To celebrate the birthday of the modest island’s monarch and his simplified film make-up regimen, let’s delve into a detailed overview of Davidson’s impressive romantic past.

A Reminder That Pete Davidson's Dating History Is Far From Bupkis

In 2015, Davidson briefly dated the star of Girl Code. They remain good friends to this day, as evidenced by their hangouts and collaborations. For instance, they were seen together following one of his comedy performances in February 2019. Moreover, Aquilino appeared alongside him in his film, The King of Staten Island, which was released in 2020.

A Reminder That Pete Davidson's Dating History Is Far From Bupkis

In her 2020 book of essays titled “No One Asked For This,” the offspring of “Curb Your Enthusiasm’s” Larry David, David, disclosed many details about her two-and-a-half year relationship with Davidson. They started dating in 2016, and David described them as spiritually connected. However, she acknowledged that Davidson’s mental health issues had caused her distress.

Before, her feelings of self-harm and suicide threats seemed to arise from seemingly insignificant events that would escalate rapidly, much like the final moments in an escape room when time runs out. But instead of a group working together, she was alone, and the clues were misleading. She remembered how, once he regained his mental wellness, she wouldn’t have the strength to revisit those feelings; she needed that time to emotionally recover from the tumultuous events of the previous week.

In the year 2018, during a family vacation, she terminated their relationship. In a moment of vulnerability, David tried to mend things with Davidson. However, she was taken aback when he subsequently informed her through a text that he had already moved on.

Two days passed, and upon logging into Instagram, she found that her former partner had posted a picture displaying his fresh finger tattoos, hiding his face with one hand. In the caption, she noticed that the words “my name,” previously inscribed in elegant cursive on his ring finger, were now concealed beneath a layer of black ink.

A Reminder That Pete Davidson's Dating History Is Far From Bupkis

Following Davidson and David’s separation, as well as Grande’s recent breakup with rapper Mac Miller, it was confirmed by TopMob News that the two were seeing each other informally.

However, the situation took a turn for the significant when the duo, who had first crossed paths during her SNL hosting two years prior, made their relationship official on Instagram and got identical tattoos within a month of their first meeting. By June 2018, they were engaged, cohabiting in a $16 million NYC loft, and sharing their living space with their adopted pig pet.

In October 2018, their passionate relationship concluded, followed by the revelation of their separation a month later. This announcement came shortly after Miller passed away due to an overdose at the age of 26.

Instead of processing the breakup through his stand-up comedy routines, Davidson chose to express himself this way, whereas Grande expressed her emotions by composing a successful song and album titled “thank u, next.

A Reminder That Pete Davidson's Dating History Is Far From Bupkis

Approximately three months following his breakup with Grande, the lead actor of “The King of Staten Island” initiated a casual relationship with Beckinsale.

According to our source, due to their frequent stays on different coastlines, their relationship is more laid-back. However, they plan to continue their conversations and enjoyable times together.

Over the span of their short-lived relationship, Davidson and the actress from Underworld went to parties, hockey matches, and even dined with Beckinsale’s parents. However, their affection cooled off after three months, according to a source, who stated that it was just “natural development,” implying that they remain in contact and maintain a cordial relationship.

A Reminder That Pete Davidson's Dating History Is Far From Bupkis

Back in August of 2019, I found myself at the heart of an intriguing speculation when I was noticed side by side with a captivating starlet, during the premiere of her film, “Seberg.” Our casual walk through Venice soon transformed into a romantic escapade as we strolled hand-in-hand, immersing ourselves in the city’s enchanting allure.

Although neither Davidson nor Qualley publicly acknowledged their romantic involvement, her mother, Andie MacDowell, revealed details during an interview with People. She expressed, “She has a lovely relationship with him, but I don’t want to intrude too much on their relationship. They get along well.

But the couple called it quits after two months.

A Reminder That Pete Davidson's Dating History Is Far From Bupkis

In October 2019, Davidson and Kaia Gerber, daughter of Cindy Crawford and Rande Gerber, started dating. They were frequently seen together in New York City, showing a strong bond and spending a lot of time together.

However, as their relationship progressed for several weeks, Kaia’s parents stepped in due to concerns, with a source revealing to TopMob News that they aimed to “provide guidance for Kaia and assist Pete during a challenging period in his life.

According to an insider familiar with Davidson’s situation, his romantic relationship with Gerber had started to diminish by January 2020 because he focused on addressing his mental health concerns through treatment. A different source added that there were no hard feelings or animosity between them.

A Reminder That Pete Davidson's Dating History Is Far From Bupkis

We can only speculate if Lady Whistledown felt annoyed when the paparazzi broke the story about Davidson being seen with the rising Bridgerton star last April. The pair were captured in England, looking quite affectionate outside of a grocery store and later taking a leisurely walk together in a nearby field.

During the course of their prolonged relationship, the pair dropped numerous hints about their partnership. They were frequently seen wearing identical silver necklaces engraved with their joint initials, “PD,” and Davidson publicly declared that the actress was his celebrity crush in a Zoom chat with university students.

Later, she shared with Elle magazine that it seemed innocent – she didn’t expect anyone to take notice. She was merely a young woman exploring relationships, and yet it sparked a discussion. Through her personal experiences, she learned many tough lessons.

According to a reliable source speaking to TopMob News, Davidson harbors deep affection for Phoebe and has been frequently traveling between New York City and the United Kingdom. The source added that this is not a bother to him, as he’s thrilled about being with her.

By August, they decided to part ways due to the immense challenges posed by the long distance between them. A source revealed this to TopMob News, stating that despite their enjoyable moments together, the situation wasn’t viable in the long run given their geographical separation. It was a wonderful experience while it lasted, but they both acknowledged that it was for the best to move on.

A Reminder That Pete Davidson's Dating History Is Far From Bupkis

For approximately a year, Davidson and The Kardashians star experienced an exciting journey, announcing their romance in October 2021 during a visit to Knott’s Scary Farm shortly after her SNL hosting stint. During this time, the mother of four introduced Aladdin to Jasmine in a whole new world—he accompanied her on a trip to Tahiti, appeared with her family on their Hulu reality series and even walked the Met Gala red carpet with her. However, by August 2022, they had returned to reality due to the challenges of long distance and busy schedules. As reported by TopMob News, despite having “a lot of love and respect for each other,” New York-based Davidson and Los Angeles resident Kardashian discovered that their differing locations and hectic workloads made it tough to sustain a relationship.

A Reminder That Pete Davidson's Dating History Is Far From Bupkis

During a talk show appearance on Late Night With Seth Meyers, the model enthusiastically praised the comic after they collaborated for a 2021 campaign shoot. She gushed, “He’s just so charming! He’s vulnerable, adorable, and his nail polish is fantastic – he looks great!” Additionally, she pointed out that he has a wonderful bond with his mother.

A Reminder That Pete Davidson's Dating History Is Far From Bupkis

Davidson resumed his acting career with his romantic interest in the movie “Bodies Bodies Bodies”, as seen at a New York Rangers game in December 2022 with costar Rachel Sennott before a date night at Universal Studios Hollywood in January. In an interview with Nylon in May, she shared that they quickly formed a strong friendship on set and their collaboration was seamless. “He’s such a seasoned actor, and working with him is my favorite thing,” she said. This is why she decided to collaborate again, joining his Peacock series “Bupkis” as his on-again, off-again girlfriend.

A Reminder That Pete Davidson's Dating History Is Far From Bupkis

Originating from Las Vegas… the individual known as the ‘Outer Banks’ star, who had a past relationship with costar Chase Stokes, was initially connected to Pete in September 2023, following her visit to Sin City for comedian Pete Davidson’s live stand-up performance at the Chelsea. According to People, this pair ended their relationship less than a year after that meeting.

Although neither has revealed the details of how their relationship started, Davidson once mentioned on the “Real Ones” podcast that he had met all his past partners at work, and none of them were in his DMs or vice versa.

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2024-11-16 14:18