The Actual Housewives of New York Metropolis’s season 16 beginner Hailey Glassman had an outrageous connection to actuality TV lengthy earlier than she joined the Bravoverse.
PR professional Glassman is certainly one of three new fulltime solid members becoming a member of RHONY in one other pseudo-reboot of the Bravo sequence, following the departures from Brynn Whitfield, Change Hassan, Racquel Chevremont and Jenna Lyons. Glassman’s fellow RHONY newcomers embrace movie star health coach Erika Hammond and make-up artist Daisy Toyeplus returning solid members Sai De Silva, Erin Lichy and Jessel Taankin addition to Carole Radziwill as a “buddy of the Housewives.”
Glassman first gained notoriety in 2009 when she began courting Jon & Kate Plus 8 star Jon Gosselin shortly after his cut up from spouse, Kate Gosselin. The connection was controversial on the time as a result of Hailey’s father, Dr. Lawrence Glassmanhad beforehand carried out Kate’s tummy tuck without spending a dime.
Hailey and Jon’s relationship was short-lived and she or he later made a sequence of very public digs about himtogether with mocking the dimensions of his anatomy.
In the case of love, former actuality star Jon Gosselin has definitely skilled his share of ups and downs. Jon was married to ex-wife Kate Gosselin, with whom he shares eight youngsters, from 1999 till the pair’s divorce in 2009. Although the Gosselins’ marriage got here to an finish amid accusations Jon had ben untrue, he (…)
Hold scrolling for a glance again at Hailey and Jon’s transient relationship.
Hailey Glassman’s Father Carried out Kate Gosselin’s Tummy Tuck
Hailey Glassman’s father, plastic surgeon Dr. Lawrence Glassman, introduced her into Jon Gosselin’s orbit earlier than they formally began courting. Jon’s ex-wife, Kate Gosselin, has confirmed that Lawrence reached out to her after seeing her complain on her TLC present about having the “jowls of a canine,” or extra pores and skin on her midsection, because of her C-section procedures.
“A plastic surgeon’s spouse occurred to see that hour particular and she or he begged her husband to do my tummy tuck without spending a dime,” Kate revealed in a 2025 Fb video shared by Glassman Plastic Surgical procedure. “She all the time mentioned, ‘I didn’t want one so I requested him to present mine to (Kate).’ That’s what occurred.”
She confirmed, “Dr. Glassman did my tummy tuck. (His spouse) contacted me by means of our manufacturing firm one way or the other … I actually screamed on the prime of my lungs. I by no means even considered a tummy tuck. I by no means even thought it was doable as a result of I knew we couldn’t afford it. The potential for it was superb.”
Controversy Over Jon Gosselin and Hailey Glassman’s Relationship Timeline
Jon and Kate Gosselin introduced that they have been ending their marriage throughout a June 22, 2009, episode of Jon & Kate Plus 8.
“I attempted to ponder (our marriage) and give it some thought,” Jon mentioned throughout the episode. “It’s simply not good… for us to be arguing in entrance of our youngsters.”
Later within the episode, he informed the cameras, “I’m harm by all of this, however I’m excited and harm on the identical time as a result of I’ve a brand new chapter in my life. I’m solely 32-years-old and I actually don’t know what’s going to occur.”
There have been stories days later that Jon had already began a brand new relationship with Hailey Glassman. In August 2009, the PR guru addressed the awkward timeline of her new relationship with E! Information by clarifying that Jon and Kate have been separated for “months” earlier than she began seeing him in Could 2009.
“Jon and Kate have moved on with their lives — it’s solely the viewers who haven’t moved on,” she demanded.
Hailey Glassman in February 2026.
Courtesy Instagram/Hailey GlassmanIn October 2009, she informed The Insider that “Kate wouldn’t say I used to be a house wrecker.”
“I’ve respect for (Kate),” Hailey pressured. “She’s like a lioness defending her cubs. That’s her turf.”
Hailey Glassman Referred to as Jon Gosselin Her ‘First Love’
In her E! Information interview, Hailey Glassman mentioned that she thought of Jon Gosselin to be her “old flame.”
“I’m not some movie star, I’m not some well-known individual — I’m only a 22-year-old lady who acquired caught in the course of all this,” she mentioned. “Take my quarter-hour, you may have it again.”
Jon Gosselin Was Accused of Dishonest on Hailey Glassman
Jon Gosselin was noticed with Star reporter Kate Main in New York Metropolis in July 2009 however he insisted that he was solely associates with Main.
“My coronary heart is all the time with Hailey,” Jon completely informed Us Weekly that very same month.
Main disputed his feedback throughout an August 2009 interview with CBS Informationclaiming that she felt “badly for (Hailey) that she doesn’t know the reality.”
“I don’t have a variety of respect for (Jon),” Main insisted. “I feel he dealt with the state of affairs very poorly. He didn’t act like an grownup or a grown man or a father. And it’s simply unhappy. I feel the celebrity has simply gone to his head and he’s on some bachelor romp.”
Hailey publicly took Jon’s aspect on the time, calling Main “cuckoo” throughout an interview with E! Information in August 2009.
“I do know what Jon tells me and I do know him,” she insisted.
Hailey Glassman and Jon Gosselin Break up in October 2009
Us Weekly reported in October 2009 that Hailey Glassman and Jon Gosselin had cut up after a whirlwind five-month romance. Days earlier, Glassman had informed The Insider that she “shouldn’t should put up with being emotionally abused.”
“We’re at a degree now the place I don’t know why I really like him,” she informed the TV present on October 28, 2009. “He will get annoyed and offended and I’m the one who will get the brunt. He’ll name me and take his anger out on me. He has ‘mantrums.’”
Later within the interview, she complained, “I cry and say why are you so imply to me? He takes it out on me. He talks over me so I can’t communicate. Typically he has hassle with the reality and he’ll dance and dance round his lies. He’s like Jekyll and Hyde. However I nonetheless love him.”
Jon responded to Hailey’s allegations by telling The Insider that his ex-girlfriend “paid a major worth to dwell underneath such a media microscope.”
“I’m grateful for her emotional help and I remorse any ache that my actions have precipitated her as she has selflessly born the pressures I’ve endured underneath the media glare,” he went on. “I’m dedicated to creating issues proper with Hailey in addition to Kate and particularly my youngsters. I ask you to please give me the chance to show myself.”
Hailey Glassman Mocked Jon Gosselin’s Anatomy
In February 2010, Hailey Glassman took a shot on the measurement of her ex-boyfriend Jon Gosselin’s anatomy.
“He was so small I didn’t suppose he would cheat on me,” she informed Steppin Out journal. “He’s hung like a 9-year-old boy. I’m critical. That is true.”
Hailey alleged that “anyone who sleeps with him will discover” the dimensions, including, “It’s very noticeable. It’s so tiny, tiny, tiny.”
The PR agent recalled Jon getting upset when she broached the subject material with him as soon as.
“He mentioned, ‘You know the way unconscious (SIC) I’m of down there,’” she remembered. “I’d inform him to his face, ‘I don’t suppose you’ll cheat on me since you’re so small.’ I’d inform him that on a regular basis.”
Jon by no means publicly responded to Hailey’s insults about his anatomy. He subsequently married his second spouse, Stephanie Leboin 2025.