Pete Davidson's Dating Secrets Revealed: What Happened After Madelyn Cline?

Pete Davidson jokes that he’s typically the “girl” in his relationships.

As a die-hard admirer putting pen to paper, I’d rephrase it this way: Six months since my split from the radiant Outer Banks star Madelyn Cline, who graced my life briefly last year, I’ve been opening up about my romantic past – and the lessons it’s taught me – in a series of candid comments.

On The Drew Barrymore Show’s January 31st episode, Pete stated, “When I’m in a relationship, it seems like I’m the one who comes to mind,” expressing that some men prefer a more reserved approach and appreciate when a woman takes the initiative.

As someone who’s shared romantic moments with notable figures like Kim Kardashian and Ariana Grande in the past, I personally appreciate a bold and assertive spirit in a potential companion.

The 31-year-old individual, who lost his firefighter father Scott Davidson in the September 11, 2001 attacks, leaving behind him, his mother Amy Davidson and sister Casey Davidson, went on to say that since he was raised in a household of women, he tends to behave in a rather feminine manner.

Pete Davidson is giving fans an inside peek at his dating philosophy.

Approximately six months following the conclusion of his 10-month relationship with actress Madelyn Cline from “Outer Banks,” the former Saturday Night Live cast member playfully speculated about the character he assumes when in a romantic relationship.

Pete mentioned during the January 31st episode of The Drew Barrymore Show that he often feels like ‘the girl’ in relationships. He explained that some men can be reserved and appreciate it when a woman takes the lead, such as saying something like, “Hey.

The actor known for playing “Dog Man” previously had relationships with Kim Kardashian and Ariana Grande, and now highlights the trait of assertiveness as being important in a romantic partner.

Raised by only women in the household, this 31-year-old individual explained that he tends to express himself in a more traditionally feminine manner due to his upbringing. His father, Scott Davidson, tragically passed away during the September 11, 2001 attacks, leaving behind Pete, his mother Amy Water Davidson, and sister Casey Davidson.

Besides Pete, other family members are also exploring the dating scene, with Pete’s mother included in this journey.

Initially, he felt apprehensive since he didn’t desire anyone to disturb his mother, he said humorously to Drew. “It’s downright frightening,” he added.

For over two decades since my father left us, she’s remained single. It was recently 22 or 23 years ago when he passed away, and ever since then, she hasn’t dated anyone. When I inquired about her romantic life, she expressed affectionately, “That’s my man.” It’s a heartbreaking sentiment to hear, but it seems like she might be yearning for companionship now – someone to share moments with so I don’t have to do it all alone as much.

And he’s ready to play matchmaker.

I can’t help but admire him – he’s truly a stand-up guy. He would be pleasant regardless, but there’s something about his demeanor when he sees her that makes him even more endearing. Just the other day, my mom shared a charming anecdote with me after she got home.

He cautioned, “I need to be careful since a few years back, you remember the charming Jon Hamm?” He added, “My mother has a massive crush on him. At that time, he was single. I know him as he frequently appears on Saturday Night Live. So, I jokingly suggested, ‘Why don’t you be extra kind to my mom?’ And he agreed, ‘No problem.’ He even said, ‘That’d be great.’

Moreover, although Pete’s mother and Jon (the star of The King of Staten Island) didn’t end up having a heated exchange, Jon commended the Mad Men alum – who married Anna Osceola in 2023 – for his compassionate nature.

Pete remarked, “He’s truly a kind soul, and he would have been kind regardless. Nowadays, he’s consistently considerate towards her whenever they meet.” Pete continued, “The other day, my mother shared an amusing tale with me.

Keep reading for look back at Pete’s dating history…

In 2015, Davidson had a brief romance with the star of “Girl Code”, but they have since remained good friends, even comedians. They were seen together after one of his comedy performances in February 2019, and Aquilino also appeared in his film, “The King of Staten Island,” which was released in 2020.

In her 2020 book of essays titled “No One Asked For This,” the offspring of Larry David from Curb Your Enthusiasm, David, disclosed many details about her two-and-a-half-year relationship with Davidson. The duo started dating in 2016, and as per her account, they were like two peas in a pod. However, she acknowledged that Davidson’s mental health issues had caused significant distress for her during their time together.

Earlier, her feelings of self-harm and suicide threats seemed to erupt unexpectedly, escalating swiftly from nothing to a crisis level, much like the final moments of an escape room when time is running out. But unlike in an escape room, there was only one person involved and all solutions appeared deceptive. She reminisced that once he had regained his mental balance, she found herself too drained to engage in such actions; instead, she needed time to emotionally heal from the turmoil of the previous week.

Following their breakup during a family vacation in 2018, David tried to rekindle things with Davidson at a moment of emotional vulnerability. However, she was taken aback when he subsequently informed her that he had already moved on via a text message.

Two days passed, and upon logging into Instagram, she found her ex had posted a picture displaying his fresh finger tattoos, with his hand concealing his face. In the caption, she noted, “The words ‘my name,’ previously written in elegant script across his ring finger, were now obscured by black ink.

A few weeks following the breakup of Davidson and David, as well as Ariana Grande’s separation from rapper Mac Miller, TopMob News reported that the two celebrities had begun casually seeing each other.

However, their relationship took a significant turn when the duo who had first met during her SNL hosting two years prior, made their Instagram debut and got identical tattoos within just a month of knowing each other. By June 2018, they were engaged, cohabiting in a $16 million New York City loft, sharing their life with their adopted pet pig.

In October 2018, their fast-paced relationship concluded, followed by reports of their separation a month later. This announcement came after Miller’s untimely death from an overdose at the age of 26.

Davidson coped with the breakup by incorporating it into his stand-up routines, whereas Grande expressed her emotions through the hit song and album titled “thank u, next”.

Three months following my breakup with Grande, I, the self-proclaimed King of Staten Island, embarked on a casual love story with none other than Miss Beckinsale.

According to our source, due to them residing mainly on different coastlines, their relationship appears informal. However, they plan on continuing their conversations and shared enjoyable moments.

Throughout their short-lived relationship, Davidson and the actor from Underworld went to parties, hockey matches, and even dined with Beckinsale’s parents. However, after three months, their romance seemed to lose momentum as a source stated it had just “reached its natural end.” They continue to converse amicably and maintain a friendly relationship.

Back in August 2019, speculations about a budding romance started circulating when the actor from Once Upon a Time in Hollywood and his co-star were seen together at the premiere of her movie, Seberg, in Venice. Later on, they were spotted enjoying a romantic walk around the city, holding hands.

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

But the couple called it quits after two months.

Davidson and Gerber, the daughter of Cindy Crawford and Rande Gerber, started dating in October 2019. They soon became nearly inseparable, frequently seen together in various locations around New York City.

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

Come January 2020, a confidant near Davidson confirmed to TopMob that his bond with Gerber appeared to be dwindling, as he shifted focus towards prioritizing his mental wellbeing by seeking professional help. Yet another insider assured there was no animosity brewing between the two of us.

It’s a hope that Lady Whistledown didn’t mind being outdone by the paparazzi when they caught Davidson with the rising star from ‘Bridgerton’ in April 2021. The photos showed them looking affectionate outside a grocery store in England, and later on, they were seen taking a leisurely walk together in a field, suggesting they enjoyed each other’s company.

During their extended period of romantic involvement, the pair provided numerous hints about their relationship. They were observed wearing personalized silver necklaces engraved with their combined initials, “PD,” and Davidson publicly acknowledged that the actress was his long-time celebrity crush during a Zoom conversation with university students.

Later on, she shared with Elle magazine, “It turns out people do care – I didn’t realize this before.” She added, “I was simply living my life as a young woman, dating, and it seems that this triggered discussions. I learned many difficult lessons through the process of just living my personal life.

According to a source familiar with the matter, TopMob News has learned that Davidson has a strong affection for Phoebe. This source also revealed that Davidson has been frequently traveling between New York City and the U.K., as he is eager to spend time with her.

By August, they decided to part ways due to the challenges posed by distance. As reported by a source to TopMob News, their amusement didn’t outweigh the hardships of being separated for long periods. It was enjoyable while it lasted, but ultimately, they felt that moving on separately was the better choice.

For approximately a year, Davidson and the star of The Kardashians embarked on an exhilarating journey, announcing their romance at Knott’s Scary Farm in October 2021, mere weeks after her SNL hosting stint. During this time, she introduced him to a new world as Aladdin, and he accompanied her on various trips, including Tahiti, on their family’s Hulu reality series, and even the Met Gala red carpet. However, by August 2022, they had returned to reality.

According to TopMob News, despite having “a lot of love and respect for each other,” Davidson, based in NYC, and Kardashian, a resident of LA, found that the long-distance aspect and their busy schedules made it challenging to sustain their relationship.

Discussing the charisma of the comic after they collaborated for a 2021 photoshoot, the model expressed her admiration on Late Night With Seth Meyers, stating, “He’s just so charming, vulnerable, and adorable. His nail polish is fantastic, he looks great!” She also mentioned that he has a wonderful bond with his mother.

When Davidson contacted her in November after his separation from Kardashian and her divorce from Sebastian Bear-McClard, she found it amusing to reconnect. A source shared with TopMob News then, “Emily finds Pete entertaining and they share playful chemistry at the moment.”

Their casual flirtation persisted for several weeks, with Emily assisting Davidson in celebrating his 29th birthday. However, a source emphasized that neither was ready to define their relationship, describing it as “casual and relaxed.” By December, she was seen getting closer to designer Jack Greer.

Davidson resumed his acting career with his romantic interest in “Bodies Bodies Bodies,” as evidenced by their public appearances together at a New York Rangers game in December 2022 and a date night at Universal Studios Hollywood with costar Rachel Sennott. In an interview with Nylon in May, she shared that they quickly formed a strong bond during the filming of “Bodies” and found working together incredibly enjoyable. She even went on to join his semi-autobiographical Peacock series, “Bupkis,” playing his on-again, off-again girlfriend.

Their friendship blossomed off-screen as well, with her stating that they discuss everything openly and their relationship feels very intimate. However, by August, multiple sources reported that the couple had parted ways.

Originating from Las Vegas… the Outer Banks actress who was previously romantically connected to her co-star Chase Stokes, was initially spotted with Pete in September 2023, following her visit to Sin City for Pete Davidson’s standup performance at the Chelsea. According to People, this romantic connection was reported. However, their relationship didn’t last long, as they parted ways less than a year later.

In contrast, neither Davidson nor his girlfriend have disclosed the details of how their relationship started, but earlier on the “Real Ones” podcast, Davidson stated, “The people I’ve dated, I met them at work. No one contacted me through DMs, and I didn’t contact anyone through mine.

2025-02-01 02:22

Pete Davidson’s Dating Secrets Revealed: What Happened After Madelyn Cline?

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