Famous Age-Gap Marriage: White House Press Secretary Karoline Leavitt (28) and Nicholas Riccio (60)

Hannah Sacks posted on People, “Karoline Leavitt, 28, Expecting Baby No. 2 with Husband Nicholas Riccio, (60)”. (December 26, 2025) And Rebecca Aizin posted on People, “Who Is Karoline Leavitt's Husband? All About Nicholas Riccio and His Relationship with the White House Press Secretary”. (December 26, 2025)

Aizin reported that 25-year-old Karoline Leavitt and ≈ 57-year-old Nicholas Riccio, a real estate developer, met at a restaurant in New Hampshire in 2022 while Karoline was running for a Congressional seat. Karoline shared on The Megyn Kelly Show,

“A mutual friend of ours hosted an event at a restaurant that he owns up in New Hampshire and invited my husband,” she recalled. “I was speaking. We met and we were acquainted as friends."

(Karoline won the Republican nomination, but she ultimately lost the Congressional seat to Democrat Chris Pappas.)

Karoline said that she and Nicholas may have an “atypical love story” but that, despite his age, Nicholas is “incredible” and “the best dad ever”. Karoline said,

“I mean it's a very atypical love story but he's incredible.” 

“He's the father of my child and he's the best dad I could ever ask for.”

27-year-old Karoline married 59-year-old Nicholas in January of 2025, but they had a son, Niko, the previous year.

Aizin wrote that Karoline related that telling her parents about her 32-year age-gap relationship with Nicholas was a "challenging conversation." However, Karoline elaborated on the Pod Force One with Miranda Devine that after her parents got to know Nicholas, his character, and how much he adored Karoline, “it became quite easy for them” to be accepting. Karoline said,

"But then, of course, once they got to know him and saw who he is as a man, and his character and how much he adores me, I think it became quite easy for them.”

Lastly, Sacks reported that on December 26, 2025, 28-year-old Karoline announced that she was expecting her second child with 60-year-old Nicholas. 

Odell’s "Gwyneth [Paltrow]: The Biography" of a Rebellious and Sexual Student

Per The Hollywood Reporter piece “Gwyneth Paltrow Burns Before Reading” (November 5, 2025), Amy Odell’s Gwyneth: The Biography “[...] debuted at No. 5 on The New York Times best-seller list [...]”. Odell’s well-read biography naturally covers Gwyneth’s career; however, for our purposes, we focused on Gwyneth’s teen years, which was done to compare Gwyneth’s teen adventures to those of celebrities like Paris Hilton.

Odell wrote that as part of her “extensively researched, [and] thoroughly reported biography”, she “interviewed more than 220 people” from Paltrow’s childhood. For example, Rober Nugent Jr. shared with Odell that he and Gwyneth dated during several summers while they participated as child actors in The Williamtown Theater Festival in the Berkshires of Massachusetts. Nugent related that he and Gwyneth shared a mutual attraction that began when he was “nine, ten years old”, which is intriguing since Nugent was “roughly three years older” than Gwyneth. Nugent shared,

“As young kids, if you call it dating, we dated. So she must’ve been attracted to me and obviously vice versa, even though I was only nine, ten years old,” Nugent said.

Odell wrote that the young couple’s "blissful summers” were mostly spent: “[...] wandering the festival grounds and exploring the woods.” One summer when Nugent was 10 or 11, and Gwyneth was 7 or 8, Gwyneth proposed. Gwyneth even procured a ring and a witness for the ceremony. Odell wrote:

“One summer day when she was around ten or eleven, Gwyneth turned to Nugent and said, “Will you marry me?” She made them fake rings and, with Jake as a witness, they held a ceremony.

However, the young marriage ended in August of that summer before Gwyneth returned to Manhattan.

After Gwyneth turned 11, she matriculated at The Spence School, a tony all-girls prep school on the Upper East Side, where she sneaked out of school, in her “hiked up” uniform skirt, to smoke cigarettes and meet up with boys at the Stoop. (The Stoop was attached to the home of The Preppy Killer.) Gwyneth shared that after she enrolled at Spence, she was “immediately drawn” to smoking. Consequently, she smoked a pack a day throughout middle school and high school.

Nancy Jo Sales related in her New York magazine profile “A Star Is Bred - Gwyneth Paltrow” (July 1996), that by the 9th grade, Gwyneth had blossomed into a “state of stunningness” and that to show off her “coltish legs” Gwyneth took to “hemming her school uniform well above her knees”. A former Spence schoolmate of Gwyneth shared with Sales that, although they all wore their uniform skirts short, Gwyneth, “[...] wore her skirt a little too short.” In addition to smoking and meeting boys at the Stoop, Sales wrote that Gwyneth showed off her coltish legs on Madison Avenue: “[...] where she would escape to smoke cigarettes and flirt with passersby.”

Odell related that while in the 10th grade at Spence, Gwyneth entered her “rebellious phase”. Consequently, she would sneak out of her 5th bedroom to go to bars with “the Posse” (i.e., four other on-the-run Spence schoolgirls). Sometimes Gwyneth would leave a note on her pillow: “I snuck out. I’m at Dorrian’s. You can punish me in the morning.” (Dorrian’s is where The Preppy Killer met his victim, 18-year-old Jennifer Levin.)

Sales related another version of the note that Gwyneth left on her pillow: “Dear Mom and Dad, I didn’t run away. I haven’t been kidnapped. I’m out at the clubs. You can punish me in the morning.”

Not only did 15-year-old Gwyneth frequent bars and clubs, Gwyneth would also attend parties in hotel rooms, or she would host a party in her town house while her parents were away.

In addition to entering her rebellious phase, Odell wrote that during the 10th grade, Gwyneth “began discovering her sexuality” as well. Consequently, after approximately 26-year-old Sheryl Berkoff, a make-up artist and then-girlfriend of Keanu Reeves, gave 15-year-old Gwyneth a “blowjob lesson” behind a movie trailer while smoking cigarettes on the set of Gwyneth’s mother’s film.

Of the blowjob lesson, Gwyneth later shared on the “Gwyneth Paltrow: Dangerous and Scintillating” episode of the Literally! With Rob Lowe podcast (07/23/2020), “I’m sure that I implemented it the first chance I got.” Furthermore, Gwyneth revealed during the podcast that 23-year-old Keanu Reeves was her celebrity crush and that it was “so cool” that, although Gwyneth was a 15-year-old “high school kid”, Sheryl treated her like a sexual young woman; thus, Sheryl made Gwyneth feel “so free”. Gwyneth said,

"I met Sheryl when I was 15 or 16. She was doing my mom's makeup on this TV movie [...] and I was, like, immediately obsessed with her. First of all, she was dating Keanu Reeves, who was my celebrity crush. And she was so cool. And she knew that I was sneaking cigarettes, and she would come smoke with me behind the trailer, and she taught me how to give a blow job, and you know, all the classic Sheryl stuff [...] And I was a high school kid [...] It was less about remembering the technique — although I'm sure that I implemented it the first chance I got. It was so cool to have someone treat me like an adult and see me as, like, a young woman and someone who is sexual. She just made me feel so free."

Rhetorical question: Did Gwyneth ask Sheryl to teach her how to give a blow job, or was the lesson unsolicited? If Keanu Reeves had given Gwyneth the “blowjob lesson”, would Vanity Fair, People, and Newsweek write about the lesson so lovingly?

Gwyneth Paltrow | Hook (1991)

Not only was Gwyneth sexual, but she also possessed a “bawdy sensibility” as well. For example, during the 10th grade, Gwyneth drew an erect penis on a cubicle in Spence’s library. After Gwyneth was confronted by the librarian, Gwyneth replied, “Come on, where’s your sense of humor?” Odell wrote that: “Gwyneth became annoyed when she had to clean it up.”

Reportedly, during her teen years, “Gwyneth dated a lot [...] and talked openly about sex.” Unsurprisingly, Gwyneth dated an older guy as well. For example, Odell wrote that 15-year-old Gwyneth “dated her cousin’s college friend”.

Odell wrote that Gwyneth was described as a “tall, beautiful, thin girl - [with] a lot of arms and legs”, a “pretty blond nepo-baby”, and “ever the extrovert”. Sales related that Gwyneth was “six feet tall with blonde hair down to her waist” and that Gwyneth’s dates included “other people’s boyfriends”. Odell and Sales wrote that Gwyneth confessed, “I kissed somebody’s boyfriend when I was 15.”

Odell wrote that, inexplicably, Gwyneth’s father gifted her “a pair of lace underwear” and that after Gwyneth made reservations at Elio’s, an Italian restaurant on the Upper East Side, patrons assumed that Gwyneth and her father were dating. Odell wrote that Gwyneth’s father said, “The women were staring daggers at me at the tables, and the guys were going, ‘Way to go.’”

Interestingly, for her senior project, Gwyneth recorded a song with Donald Fagen, the lead singer of the band Steely Dan. Arguably, Steely Dan’s most popular song is "Hey Nineteen", which is about a man who rejects the sexual advances of a teen groupie.

Per Odell, at the end of the 1990 season of The Williamtown Theater Festival, 17-year-old Gwyneth attended “an end-of-season party at a bar” with Christine Lemme and Christine’s summer fling, who was in his twenties, but that didn’t stop Gwyneth from groping him (i.e., SA). Subsequently, Christine’s fling informed Christine, “Gwyneth just felt me up!”

As part of a multi-million dollar marketing campaign, in January of 1991, the fashion brand Esprit sent out postcards to young customers with the question: “If you could change the world, what would you do?” Odell related that: “Gwyneth was on the audition circuit, and she was one of the pretty people whose photo ended up on the casting board [...]”

And what was 18-year-old Gwyneth’s reply to Esprit’s question about how she would change the world? Gwyneth replied: “i would distribute condoms in every high school in america.” Odell wrote:

The text ran alongside a black-and-white image of Gwyneth in her own jeans, white T-shirt, and cardigan. She looks musingly off to the side, her hair cascading undone over her shoulders

Over twenty years later, Esprit, ignoring the fact that Gwyneth's initial response was a consequence of her sexual nature, repurposed her response in a 2019 HIV and AIDS prevention campaign.

Gwyneth Paltrow | Flesh and Bone (1993)

And due to a “ease about her” and the fact that she was “Hollywood royalty”, Gwyneth was cast as Ginnie in Flesh and Bone (1993). Per Odell, Risa Bramom Garcia, the casting director, opined that Gwyneth possessed, “[...] a combination of earthiness and depth and intelligence, which was really rare for an actor and especially a nineteen-year-old.” However, the role required nudity, which wasn’t a problem for 19-year-old Gwyneth. Per Odell, Gwyneth didn’t “flinch” when she was informed about the nude scene, because Gwyneth said that she: “[...] would do what[ever] was necessary to play the role effectively.” Odell wrote that Gwyneth’s nude scene was cut from the film, but that isn’t true. Consequently, Gwyneth’s topless scene has been posted on a variety of porn websites that are dedicated to celebrity nudes.

It turns out that Gwyneth's teen years were, unsurprisingly, very similar to Paris Hilton’s. For example, Paris shared in Paris: The Memoir that in the sixth grade at The Buckley School, a prestigious private school in Los Angeles, the tenth-grade boys invited her to sneak off campus. “Sure!” Consequently, like Gwyneth, Paris rolled up her prep schoolgirl skirt “and styled it short.” Reminiscing on the day, she wrote, “I just liked the attention.” And it was at The Buckley School where, during a sixth grade game of Spin the Bottle, Paris had first kiss. (In addition to wearing her sixth grade prep school skirt short, by 8th grade, 14-year-old Paris “found ways to shorten” her Catholic schoolgirl plaid skirt as well.)

Per Paris, since she was “frequently grounded”, she began sneaking out of the house in the 8th grade. Paris would climb out of her bedroom window, “slid down the drainpipe”, and she “maneuvered down to the ground”. Paris was determined “to wear makeup, go on real dates, or hang”. After Paris turned 15, she moved to Manhattan with her parents and siblings into a 2,500 square-foot condo in the Waldorf, but that didn't stop Paris from sneaking out.

Paris’ source for nightlife entertainment was Time Out New York, which she used for: “[...] scoping out the best parties and music and DJs”. Paris would sleep “most of the day” and “[a]fter everyone went to bed” she “headed out”. Paris would “dance and go wild until the morning”, then she “slipped past the doorman”, “took a shower, and fell into bed as everyone else got up to get ready for school.” Sometimes Paris: “[...] crashed at a friend’s house, slept all day, and went back out the next night.” Lastly, Paris shared that after she turned 16, with the help of the Wonderbra, she became a woman. Paris wrote:

“I looked in the mirror, and there was a woman looking back at me. It was helpful that Wonderbra was having a moment.”

Lastly, Odell wrote that Gwyneth and Mr. James Dawson, Gwyneth’s 9th-grade biology teacher, had “a unique connection”; however, it’s unclear if Gwyneth and Mr. Dawson had a student-teacher affair like Paris had with Mr. Abercrombie, whom she described as “handsome” with “tousled hair” and “penetrating eyes”. Their affair was their secret. A secret Paris wrote that was a “[...] secret like candy under my pillow.”

LAW & ORDER: SVU | St. Tabitha Prep School's Teen Hookers

On “Hooked” (2005), the 15th episode of season 6 of Law & Order: Special Victims Unit, while looking at a topless lady through a telescope, a Boy Scout said, “I got something great and bare right here.” Consequently, another Boy Scout demanded, “Let me see. Let me see. Let go [of the telescope]!” However, the second Boy Scout couldn't find the topless lady, but he did discover the dead body of Lisa, who had just turned 15. Lisa was wearing “an $800 cocktail dress”, her hot pink panties were around her ankles, and there was, “Trauma to her vaginal area.”

Allison Downey, Lisa’s cousin, told Detective Benson and Detective Stabler that she let Lisa use her driver's license, because Lisa was “going out with this college guy,” and Lisa wanted to get into clubs with the older guy.

The headmistress at Saint Tabitha Prep School told the police that the only time Lisa got into trouble was over the “sex bracelets”, which were different color bracelets that all the schoolgirls in Lisa’s grade wore; thereby, “[...] signaling which sex acts they’re willing to perform.” 

Headmistress, “Yellow’s hugging. Purple’s kissing. Red is for a lap dance. Blue is for oral sex. And don’t make me say what black is for.” 

To get more information about Lisa, the headmistress referred Benson and Stabler to Angela Agnelli (Hayden Panettiere), Lisa’s best friend, whom shared with Benson and Stabler that the boys in her class called her and Lisa sluts, because Angela and Lisa weren’t interested in boys, since boys were, “[...] way too immature.”

The police discovered Lisa’s profile on HotPersonals.net, where Lisa went by 18-year-old QueensTeen, and she posed in a pink, cleavage-revealing, very cropped top. Lisa posted on her Hot Personal’s profile that she liked to have fun. She asked: “Your place or mine?” She exclaimed: “Let’s hook up!” And she demanded: “[S]end me a message!”, which a lot of men did. 

It’s common for media with an age-gap relationship theme to include a girl-on-girl sexual motif as well. Thus, we weren’t surprised when another Saint Tabitha Prep schoolgirl shared with Benson that Lisa was “into girls [...] for a while, too, when she got tired of boys. Until she started doing older guys she met on the Internet.” [Emphasis added] Thus, when Lisa was 14 and possibly younger, she was “into” girls and boys, but that was only until she started “doing” men. 

Interestingly, Benson wanted to know why Lisa wasn’t afraid to have sex with (older) strangers, but the schoolgirl questioned why Lisa would be afraid to have sex with (older) strangers.

Benson, “She wasn’t scared of having sex with people she didn’t know?”

Schoolgirl, “Why would she be?” “Lisa was looking for mature men.”

Angela gave Benson and Stabler more information about Lisa’s college guy. Angela said that Lisa and the college guy, the rich Andy Wall, met online. Subsequently, Andy took Lisa to clubs and purchased her clothes. Angela shared, “She was really into him until he started getting jealous.” Why was the wealthy college student jealous of a 15-year-old girl? It was because Lisa was, “[...] hooking up with other [older] guys.”

Benson found designer clothes in Lisa’s wardrobe. “Thousands of dollars worth.” The clothes were from Her Boutique, where Benson and Stabler, via security footage, saw Brian, the boutique’s middle-aged manager, go into a fitting room for over ten minutes with Lisa. Naturally, Benson and Stabler asked to speak with Brian. They were told that he was doing “sales inventory in the stock room”, but Brian was actually receiving oral sex from Angela in the stock room.

Naturally, Benson was unzipped after she discovered Angela performing oral sex on a middle-aged man; however, Angela didn’t understand why Benson was so upset, because Angela said that Brain liked to buy her “pretty things” (e.g., Louis Vuitton, Prada, and Dolce & Gabbana) in exchange for (oral) sex. And Angela argued that she used to perform oral sex for free; so, why not get paid?

Angela, “I don’t see what you’re so upset about.”

Benson, “You’re selling yourself for clothes.”

Angela, “No, I’m not. Brian just likes to buy me pretty things.”

Benson, “Yeah, in exchange for sex.”

Angela, “I do not have sex with him [...] It’s only oral.”

Benson,“Oral sex, Angela”

Angela, “So what? It’s the same thing I usually do when I hooked up. At least this way I get something out of it.”

Benson, “Louis Vuitton bag. Prada shoes. Dolce Gabbana top. That’s at least two grand right there.”

Lisa confessed to Benson and Stabler that she and 14-year-old Lisa began “hooking at the mall” by luring johns via window shopping. However, a few months prior, at the suggestion of Jerome, Lisa started “turning tricks” at The Barrington hotel. Jerome, the desk clerk at the “high-class” hotel, told Benson and Stabler that Lisa told him that she was 19 and that Angela and Lisa paid him for john referrals. In addition, Jerome referred Benson and Stabler to Dr. Derek Tanner, a physician and one of Lisa’s johns.

Dr. Tanner informed Benson and Stabler that he was in New York from Rhode Island for a convention when “beautiful” Lisa approached him in the lobby of The Barrington and that, before they had “incredible” sex, Lisa claimed that she was 21. Consequently, Dr. Tanner was “addicted”; so, despite being married, he moved to New York to be with Lisa, and “[...] gave her everything she wanted!” Unfortunately, Dr. Tanner was murdered in his apartment, and a search of the crime scene turned up Angela’s uniform scarf from Saint Tabitha Prep. Subsequently, Angele’s school locker was searched, where a teen sex tape was discovered. In the sex tape, Angela and Lisa, in their schoolgirl uniforms, engaged in a “little girl-on-girl action” before a three-way with Dr. Tanner. 

In the sextape, Lisa encouraged Angela, “Don’t be shy. Don’t be shy.” And after Dr. Tanner grabbed Lisa by her blonde strands, Lisa said, “Hey, baby. I got something for ya!” Dr. Tanner paid Angela and Lisa $500 for the tryst. And Angela said that Lisa made, “A lot of other videos,” which were “hardcore”. Lisa even took Angela to a porn store to proudly show Angela her videos on display, and Lisa encouraged Angela to do teen porn as well. 

Lisa referred Benson and Stabler to Max of Max Long Studios, where they discovered the DVD Trudi, Madly, Deeply featuring a topless Trudi Strutz (i.e., 15-year-old Lisa). Here’s the DVD’s subtitle:

DEEPER than Ever!

Trudi DOES IT ALL

And sweeter than

You’ve EVER Seen her!

Max said that Trudi was 19-year-old Allison; however, Stabler informed Max, “No, that’s Lisa. She’s 15.”

Interestingly, Benson opined that Lisa’s teen promiscuity led to her being a teen prostitute and, consequently, a teen porn star.

Stabler asked, “How did this happen? Six months ago, she was just another 15-year-old.”

Benson replied, “Till she started hooking up with half of Queens. After that, it’s no big deal to have sex for designer clothes or prostitute yourself in a hotel.”

Capt. Don Cragen, “And she ends up as Trudi Strutz, porn star.”

Lastly, “Hooked” reminded me of the Roman schoolgirl prostitutes in Netflix's Baby (2019), and the Japanese schoolgirl prostitutes in Love & Pop (1998).

Olivia Nuzzi's "Jailbait": An "Outrageous" but "Undeniably Infectious" Song

In a previous post, we related that when Olivia Nuzzi, the former Vanity Fair editor, was an 18-year-old student at Middletown High in New Jersey, she initiated an age-gap affair with 52-year-old Keith Olbermann, the former MSNBC host. Nuzzi was 25 when she began dating her future fiancé, 44-year-old journalist Ryan Lizza, a current CNN analyst. Nuzzi was 30 when she began a “digital affair” with 60-year-old Robert F. Kennedy Jr.. And when Nuzzi was 16, with the stage name Livvy, she recorded “Jailbait".

In the first verse, Nuzzi sang about the undeniable allure of a nymphet, and she shared that she was shameless; however, she warned that an age-gap affair with a 16-year-old could get a man 20 years in jail.

Verse:

Bad things happen when you hear my name

Deny your attraction - but I've got no shame

Sixteen will get you twenty, I've got you locked for life

Don't even think about it, because baby I'm

However, in the pre chorus, she warned men that after being with her, they’ll desire more.

Pre Chorus:

Not your girlfriend

Not the girl next door

Not your girlfriend

I'll give you just enough and leave you wanting more

The 16-year-old sang in the chorus that despite being jailbit, she was irresistible, but warned men that they could look at her but not “play” with her.

Chorus:

Jailbait

I'm jailbait

You try to stay away, but you can't obey

Jailbait

I'm jailbait

You look, but you can't play

Cause I'm jailbait

Ja-ja-ja-ja-jaibait

Ooh, they call me jailbait

In the second verse, Nuzzi sang about the precariousness of “craving sin” (i.e., craving sex with jailbait), which she referred to as an “illegal dream”, and she warned about the potential inability to resist a “teenage queen”.

Verse:

Craving sin, we walk a fine line

A game I win, that word I define

A teenage queen, right in front of you

Illegal dream, killer to pursue

In the bridge, she serenaded that bad things happen to men whom prey upon and “lust criminally” after jailbait, which she, once again, described as an “irresistible” conundrum.

Bridge:

Bad things happen to those who (pray) prey

A basic instinct to die another day

Sixteen will get you twenty, lust criminally

Irresistible, that's why they call me…

In a press release for the “Jailbait”, Nuzzi described the song as: "Offensive", "vapid", "frothy", "bubblegum", "outrageous", "morally bankrupt", and "undeniably infectious". In addition, Nuzzi related that “Jaiilbait” is about “underaged, hyper-sexualized girl[s] in society” whom take semi-nude selfies. Nuzzi wrote that the “sexy” song is about the “obsession with youth and beauty”, which she condoned. And she confessed that she’s the embodiment of jailbait. Nuzzi:

“Jailbait” is about the role of the underaged, hyper-sexualized girl in society. That girl who takes half naked photos of herself in the mirror with her camera phone. It's about pornographic ideals infiltrating our collective consciousness — this obsession with youth and beauty. I'm not saying that any of this is wrong, I'm simply stating that it is. This song is me coming to a societal realization."

And simply put, I am the definition of jailbait.

On her MySpace page, Nuzzi posted that as a 16-year-old singer/songwriter of songs like “Jailbait”, she planned to invade the listener’s consciousness and their worlds. Nuzzi:

Livvy (Olivia Nuzzi) is the future, and Livvy is the past. Preparing to dominate the world and show you the way a pop object lives. Livvy has no off switch, and life is a performance in her eyes. This sixteen year old singer/songwriter plans to invade your consciousness with her killer pop hooks and become the center of your world.

Lastly, Nuzzi’s album was planned to be a “conceptual expansion on "Jailbait", which “explore[d] the good and the bad of this all-consuming porniness”. Porniness?

Famous Age-Gap Relationship: Oliva Nuzzi (18) and Keith Olbermann (52)

Keith Olbermann and Oliva Nuzzi

Ryan Lizza, the CNN analyst and former fiancé of Vanity Fair’s former West Coast editor Olivia Nuzzi, posted “Part 1: How I Found Out” on his Telos News Substack. In the post, Lizza shared that when Nuzzi was a teen, from her “unhappy home in suburban New Jersey”, she randomly “messaged” 52-year-old Keith Olbermann, the former MSNBC host. Consequently, Nuzzi moved into Olbermann’s Manhattan apartment, where they began an age-gap affair. Lizza wrote:

Not that long ago, I had helped her untangle herself from an unusual relationship with Keith Olbermann, the former MSNBC host. She had messaged him out of the blue. They started talking, and soon after, she fled her unhappy home in suburban New Jersey and started living with Keith in Manhattan. 

Rhetorical question: Did Nuzzi initiate the affair with Olbermann because she was looking for a loving (age-gap) relationship, or was she looking for a Sugar Daddy, or both? I ask because Lizza posted that Olbermann paid for Nuzzi to attend Fordham University. (The Lincoln Center campus, I presume.). He dressed her in designer dresses. He draped her in Cartier. And he paid for her luxury West Village apartment. Lizza wrote:

He paid for her to attend college, outfitted her in Tom Ford and Hervé Léger dresses and some $15,000 worth of Cartier jewelry. Later, he covered her rent and furnished her apartment in a doorman building in the West Village. 

There are a number of conflicting reports about exactly when Nuzzi and Olbermann’s age-gap affair began; however, the correct report is that it began when Nuzzi was an 18-year-old high school student at Middletown High. 

Olbermann shared with the New York Times that 18-year-old Nuzzi moved into his apartment in a “Trump building on the Upper East Side”, where they had two Maltese puppies and an “marriage-y” age-gap relationship.

Ginia Bellafante related in the New York Times piece “In This Scandal, the Journalists Are the Story” (Nov. 21, 2025):

Mr. Olbermann had lived with her for a while in a Trump building on the Upper East Side, “if you can believe the irony,” he told me. He said he had discovered her writing on Twitter, where she provided witty political analysis as a student, and he wondered if she might be a good fit for the TV show he had hosted in those days.

They met for dinner. She was 18. He was 52. Instead of working together, they began dating, he said. They got two Maltese puppies and James Thurber-inspired tattoos. “It was marriage-y,” Mr. Olbermann said. “It was very much an at-home-with-the-dogs sort of thing.”

However, a day after their conversation, Olbermann shared with Bellafante that he and Nuzzi didn’t have sex until after Nuzzi turned 19, which is extremely hard to believe. 

It’s worth noting that prior to his relationship with Nuzzi, Olbermann was 47 when he had an age-gap affair with 23-year-old journalist Katy Tur. Nuzzi was 25 when she began dating 44-year-old Lizza. Nuzzi was 30 when she began a “digital affair” with 60-year-old Robert F. Kennedy Jr.. And when Nuzzi was 16, she recorded “Jailbait”, which included the salacious lyrics like: “Bad things happen when you hear my name / Deny your attraction, but I’ve got no shame / Sixteen will get you 20 — I’ve got you locked for life” 

AFTER THE HUNT (2025): Alma's (Julia Roberts) Affair with Father's Best Friend

Here’s IMDb’s synopsis for After the Hunt (2025):

A [Yale] college professor (Alma Imhoff [Julia Roberts]) finds herself at a personal and professional crossroads when a star pupil (Maggie [Ayo Edebiri]) levels an accusation against one of her colleagues (Hank [Andrew Garfield]) and a dark secret from her own past threatens to come to light.

To elaborate a bit, Maggie, a PhD student, accused Frank, a Yale professor, of sexual assault. Frank confessed that he flirted with students, but he claimed that he never had sex with a student. Alma was apprehensive about supporting Maggie, but not because Alma supported Frank. Alma didn’t support Maggie due to a “dark secret”, which was that when Alma was 15-years-old, she falsely accused her father’s best friend and co-worker of statutory rape. 

In addition to confessing to her husband that she lied about being sexually assaulted by her father’s best friend, Alma shared that she and her father’s best friend were actually in love. 

Alma, “I wanna share something with you.I told you when I was a child that my father's best friend sexually assaulted me, abused me. None of that is true. We were in love.”

Alma described her father’s best friend as kind and handsome. So much so that she would stare at him and stalk him. And he was the center of her attention and her reality.

Alma, “He was so kind, he was so handsome, I could just stare at him from across rooms. I would go to work sometimes with my father, just so I could see him. I couldn't focus in class, school, my friends, just everything felt so pedestrian, except for him. He was the only thing that felt real to me."

Shortly after her 15th birthday, Alma was kissed by her father’s best friend, and six months later, at Alma’s insistence, they had age-gap sex, which resulted in that time period being the “happiest time” in Alma’s life. 

Alma, “He kissed me for the first time the day after my 15th birthday [...] Six months later, maybe. He said I was too young, but I had insisted. It was the happiest time of my life."

However, her father’s best friend suddenly ended their age-gap affair and started openly dating someone “more appropriate”, which Alma referred to as “cruel”, because she was crushed. Consequently, to get revenge, she reported him for (statutory) rape. Although she eventually retracted her accusation, he committed suicide. 

Alma, “Then out of nowhere, he said that he met someone else and someone that was more appropriate. He started bringing her to my parents' parties and throwing her in my face like he was trying to prove how little he cared. It was so cruel. So I made up a story that I knew would hurt him the most. And three years later, he committed suicide. I had already retracted the story by then, but it didn't matter. I'd wanted to hurt him the way I thought he'd hurt me, and I did.”

In an attempt to console Alma, Frederik, Alma’s husband, reminded her that she was very young. Very interestingly, Frank said that “all young girls” have adult-like desires, but that it was the responsibility of adults to resist satisfying those innocent desires. 

Frederik, “Alma, you were very young. All young girls want adult things to happen to them. Sooner than they're ready for them all the time, but it's always the adult's job to protect the innocence of a child."

Alma responded to her husband by reminding him that, initially, her father’s best friend rejected and refused her sexual advances but that she didn’t give him a choice and insisted that they have an age-gap affair.

Alma, “No, I didn't give him a choice.”

Frederik, “There's always a choice. It doesn't matter if you wanted him. It doesn't matter if you threw yourself at him. He should have rejected you outright.”

Alma, “No, he did. He did. He refused me.”

Alma confessed that she destroyed a good man with a lie, but her husband replied that it was not a lie, because the truth was that she was underage, but Alma retorted that the truth was that she’s (still) in love with her father’s best friend. 

Alma, “He was a good man, and I destroyed him with a lie.”

Frederik, Alma, it wasn't a lie. You keep thinking he did nothing wrong. You keep blaming yourself. Do you think you can allow yourself to see the truth in that?

Alma, “The truth is that I love him.” 

Interestingly, Frederik put all the blame on the best friend for the illicit affair, and Alma blamed herself, but, some would argue that, in reality, the best friend and Alma were to blame.  

Lastly, per Justin Change and the New Yorker: “After the Hunt” Is a Pleasurably Ludicrous House of Cards (October 3, 2025)