Big Boobs Jenny and Fun Slut Vanessa | GOSSIP GIRL [Book 2] Recap (Part 2)

Gossip Girl: You Know You Love Me (Book 2): Jenny, Vanessa and Chuck

[The original CW Gossip Girl series was called “Mind-blowingly inappropriate.” by the Parents Television Council, “Very bad for you." by the San Diego Union-Tribune, and “A nasty piece of work.” by the New York Post. However, I would argue that the young adult novel series is inarguably more salacious. I plan to recap books 1-8, 13, and 14, which were written by Cecily von Ziegesar and are based on Ziegesar's experiences at The Nightingale-Bamford School, an Upper East Side all-girls prep school.]

Jenny

As you may recall from book 2 part 1, Jenny is a 14-year-old “lowly ninth-grader” at Constance Billard School for Girls, which is a “small, elite, all-girls school on East Ninety-third Street”, where uniforms are required. And you may recall that Ziegesar wrote that during foreplay with Blair, Nate’s erection “stuck out, tentlike” in his “red-and-white checked boxers”. Interestingly, likewise, Ziegesar wrote that Jenny’s “enormous” “boobs” caused her “pink nightgown” to form a “tentlike triangle”. In terms of Jenny, Ziegesar penned: 

She stood in front of the mirror holding her breath and pushing her stomach out as far as it would go. It still didn’t stick out as far as her boobs, which were enormous for a ninth-grader. Her pink nightgown fell in a tentlike triangle from her breasts to her knees [...] 

“Freak,” Jenny Humphrey whispered to her reflection.

(Note: Recall that in book 1, Ziegesar referred to Jenny’s “boobs” at least nine times. For instance, in book 1, Ziegesar wrote that Jenny’s “boobs” were: “[...] incredibly huge. At fourteen, she was a 34D.")

Consequently, when Jenny met Nate at “the edge of Sheep Meadow”, Nate, “tanned” with “dark honey-gold” hair, immediately noticed Jenny’s “huge” chest. Ziegesar wrote:

She reached the edge of Sheep Meadow and stepped onto the grass.

Jenny looked up. [Nate] […] the golden boy, standing only thirty feet away, hands on his hips, his green eyes sparkling. His cheeks were flushed pink and his forehead was beaded with sweat. Jenny wanted to taste it.

 

Nate noticed Jenny’s chest. Man, was it ever huge. He couldn’t let her get away, not without Jeremy and the other guys getting a chance to check her out.

That’s correct. Per Ziegesar, Jenny wanted to taste Nate’s sweat. (LOL) And Nate wanted the other seniors to check out Jenny’s huge chest. 

After mingling in Central Park, Nate took Jenny to his bedroom in his Upper East Side (triplex) townhouse, which had red marble floors and famous artists like Renoir, Sargent, and Picasso “on every wall”. 

After Nate said, “Let’s go upstairs,” Jenny followed Nate to his bedroom, which had an “antique sleigh bed” and an “ultramodern, ultracool desk with a wafer-thin laptop sitting on it”. Without being asked, Jenny sat “nervously on the edge of the bed”, where she searched Nate’s “emerald green” eyes and shared,  “I’m only fourteen”. What was 17-year-old Nate’s response? Ziegesar wrote:

Nate reached up and touched her curly brown hair, combing it ever so gently with his fingers. Then he put his hand down again. “I know,” he said. “It’s okay.”

Although, Ziegesar left it flirtatiously ambiguous, based on forthcoming chapters, readers can safely infer that Nate did not have sex Jenny the first time she sat on his antique bed. 

In the Gossip Girl post “EVERYBODY’S DOING IT”, Gossip Girl was asked about her thoughts on “older boys dating young girls”. Gossip Girl opined that “a college senior dating a high school sophomore” is a bit of a problem, that “a high school senior dating a college freshman” is “okay”, but a 12th grader dating a 9th grader is “pushing it”; however, in what most people, I would imagine, would consider to be a counterintuitive and controversial stance, Gossip Girl opined that age-gap affairs “work better” when the “the girl is the younger one”. Ziegesar wrote:

Dear GG,

What do you think about older boys dating younger girls?

—Sneaky

      

Dear Sneaky,

It definitely depends on the age difference and the circumstances. For instance, if you were a college senior dating a high school sophomore I would say you had a bit of a Woody Allen-Soon Yi Previn problem. If you were a high school senior dating a college freshman, that would be okay. A high school senior dating a high school freshman is pushing it. It seems to work better when the girl is the younger one, mainly because we mature much faster—in all ways.

—GG

Notes: 

1. Ziegesar’s Woody Allen-Soon Yi Previn reference is about Woody Allen’s affair with Soon Yi Previn, which began when Soon Yi was Woody’s teen stepdaughter. For further information about Woody and Soon Yi’s affair and eventual age-gap marriage, reference the Substack piece “The Same Thing Only Different: Nympholepsy in Woody Allen’s Art and Affairs”

2. In a (somewhat) related note, in the FAMILY MATTERS post, Gossip Girl encouraged what she called “innocent flirting with your stepbrother-to-be”, because it “isn’t sick or illegal”. And she described what some would refer to as incest as “pretty fun and pretty damned convenient”; especially “if you live in the same house!” 

Woody Allen and Soon Yi Previn

One reason that readers may infer that Nate and Jenny did not have sex (yet) is that after Jenny met Nate on the steps of The Met, she thought: “Oh my God, [...] He’s about to kiss me.” He didn’t. The arrival of Nate’s friends (temporarily) prevented Jenny from getting what she so desperately desired.  

By this point in book 2, readers are up to about ten references to Jenny’s boobs. [I lost count.] Unsurprisingly, the count continues to rise up until the end of book 2. For example, after Jenny joined Nate and his friends on The Great Lawn, her “big boobs’ were spotted by none other than Dan, Jenny’s brother. Of Dan, Ziegesar wrote:

Puffing away, he stared across the grass. A short girl with big boobs and curly brown hair was playing soccer with four boys he recognized only vaguely. It was his sister, Jenny. Since when did she hang out in the park with those boring, preppy, Upper East Side assholes?

Recall from book 1 that Vanessa, another Constance schoolgirl, was in an age-gap relationship with a Brooklyn bartender. Does that make it less surprising that, over hummus and hot chocolate, Vanessa encouragingly referenced Jenny’s “rack”? Ziegesar wrote:

They walked to a café that specialized in Middle Eastern food and ordered hummus and hot chocolate.

“So, Jennifer. With a rack like that, how come you don’t have like, seven boyfriends?” Vanessa said, pointing directly at Jenny’s chest. 

Hummus and hot chocolate?! Seven boyfriends?! 

Recollect that Dan referenced his sister’s boobs in book 1. For example, Ziegesar wrote in book 1 that even Dan “could not deny” that his sister’s “boobs were really huge.” However, it turns out that Dan referenced his sister’s boobs in book 2 two times! The second time happened at the St. Claire Hotel during Eleanor and Cyrus’ wedding reception, where Ziegesar wrote that Dan recognized his sister’s “enormous cleavage”. Ziegesar wrote:

Dan slipped into a seat at the end of the St. Claire Hotel bar and ordered a double scotch on the rocks. With trembling hands he pulled a Camel out of his coat pocket and lit it.

Dan’s chest convulsed in a sob and he slumped forward, resting his forehead against the edge of his glass. Out of the corner of his eye, he saw a familiar shock of curly brown hair, the enormous cleavage, the tiny figure.

His sister.

And next to her, with his hands all over her enormous cleavage and tiny figure was that rich bastard, Nate.

Once again, Ziegesar left it flirtatiously ambiguous about what happened between Jenny and Nate in Nate’s bedroom; however, readers learned later that they did not kiss on that occasion, because Ziegesar wrote that the first time Jenny and Nate kissed was while they: “were sitting beside the boat pond in Central Park,” where “Nate pulled her toward him. They both kept their eyes open, smiling as they kissed.” (Note: “Jenny had [previously only] kissed two boys during a kissing game at a party once [...]”) 

However, later in book 2, Gossip Girl gossiped on the NOBODY DOES IT BETTER post that: “Word has it N and J have been hooking up after school every day. Poor B[lair].” Interestingly, in book 1, Ziegesar wrote that Blair and Nate “had done everything but” have actual sex. Is that what Ziegesar is implying Nate and Jenny did every day after school?

Vanessa

In book 2, readers learned more about Clark, Vanessa’s 22-year-old boyfriend. (Recall that Gossip Girl posted that “a high school senior dating a college freshman” is “okay”. But at 22, Clark would be more like a college senior.) Ziegesar penned that Clark, a bartender at The Five and Dime, a “dimly lit” bar in Williamsburg, had “red sideburns and beautiful gray eyes”. (Note: Per Google, someone with red hair and grey eyes is extremely rare and appears in less than 1% of the entire human population.)

Despite the fact that Vanessa, who dreamed of being a film major at  NYU, was still a (prep) schoolgirl who was sitting in a bar, Clark wasn’t shy about openly expressing his age-gap desires. For example, Clark “ran his fingers through Vanessa’s short-cropped black hair” and “blew her a kiss”. Likewise, Vanessa wasn’t shy about openly expressing her desire for an older boyfriend. Ziegesar wrote:

Clark came over and ran his fingers through Vanessa’s short-cropped black hair.

Clark was the bartender at The Five and Dime [...] Clark was twenty-two. He had red sideburns and beautiful gray eyes

[Vanessa] watched Clark’s butt as he bent over to stock the bar fridge with more bottled beer.

“Hey boyfriend,” she yelled at him. “I’m lonely.”

Clark looked over his shoulder and blew her a kiss.

Thank God for Clark, Vanessa thought.

However, because it was “kind of fun to be such a slut”, Vanessa’s age-gap affair with Clark didn’t stop her from flirting with Dan. For example, during the wedding reception at the St. Claire Hotel bar, Vanessa kissed Dan on his “quivering lips”. Ziegesar wrote:

Vanessa picked a ball of lint off her fishnets and flicked it onto the bar floor. She couldn’t believe she was actually flirting with Dan. She hadn’t even broken up with Clark yet! But it was kind of fun to be such a slut.

She leaned forward and kissed Dan on his quivering lips. “Right,” she said, her mouth still full of nuts.

Gossip Girl

Interestingly, in the Vanity Fair piece “‘Gossip Girl Was Me’: Cecily von Ziegesar Talks Manhattan vs. Cobble Hill” (2020), Ziegesar related that she was, in fact, Gossip Girl. Ziegesar said, “Gossip Girl wasn’t Dan in the books. She was the omniscient narrator. Gossip Girl was me,” which (some) feminists [parents] may find interesting when one considers that Ziegesar slash Gossip Girl encouraged schoolgirls to “break out those credit cards and hit Bendel’s and Barneys for some [...] sexy fishnet tights, [and] little wool skirts”. Not only did Ziegesar write that bulimic Blair vomited her quenelle, but Gossip Girl encouraged: “The way to any girl’s heart is to tell her she looks tiny. Girls kill to be tiny.” And what was Ziegesar slash Gossip Girl’s advice on how to handle “senior stress management”? Materialism, alcoholism, and (teen) sex. Ziegesar/Gossip Girl posted: 

It’s time to break out those credit cards and hit Bendel’s and Barneys for some cool new boots, sexy fishnet tights, little wool skirts [...] 

Here’s my recipe for senior stress management: Mix one gorgeous boy with a nice new pair of leather boots, a new cashmere sweater, a long night out, and several drinks. Stir in a very late morning and hot chocolate in bed.

Chuck Bass

Lastly, recall that in book 1, Ziegesar wrote that, due to her alluring looks, Serena was “a full-on groper magnet”; thus, after Cyrus kissed Serena on both cheeks, hugged her a little too tightly, and patted Serena on the hip, Ziegesar penned that Serena didn’t flinch, because she was used to “horny European gropers”. And you may recall from book 1 that after Chuck asked Jenny to introduce him to her breasts, he gyrated his crotch against her ass on the dance floor at The Met, and then Chuck took 14-year-old Jenny into the ladies' room, where he “pulled her dress down so he could get at those massive jugs”. Well, Chuck isn’t mentioned much in book 2, but, unsurprisingly, YA readers learned that he’s up to his old ways. For example, on the dance floor at the wedding reception at the St. Clairel, Chuck promptly groped two Constance schoolgirls: Kati Farkas and Isabel Coates. Ziegesar wrote:

Chuck grabbed both Kati and Isabel’s hands and twirled them away, his hands sliding down their backs to their butts within seconds.

Famous Age-Gap Couple: Michael Wolff & Victoria Floethe

Micheal Wolff's Petronella Wyatt

I've read a number of Michael Wolff's page turners - including Too Famous, which is peppered with nympholepsy. For example, Wolff wrote that, in terms of his affair with his step-daughter, Woody Allen said, "the heart wants what it wants". Wolff related that Petronella Wyatt, a friend of Rupert Murdoch's daughter, said that, [among a number of other famous elderly men], Murdoch ogled her when she was a nymphet. And per Wolff, Jeffrey Epstein told Steve Bannon that one of Epstein's masseuses, a 14-year-old whom said she was 18, told the police that she lied about her age: "[...] because she was afraid she would never be allowed into the house and never be invited back."

Victoria Floethe and Michael Woflff

In addition to Wolff's books, I've been (curiously) impressed by Wolff's impeccable since of style, which caused me to be doubly astonished when I read Richard Johnson's Page Six headline: "Michael Wolff expecting a baby with girlfriend 30 years his junior" (February 6, 2015)

Johnson wrote that 61-year-old (married) Wolff starting dating having an affair with 34-year-old Victoria Floethe in 2009 (i.e., Wolff was 55 and Floethe was 28).

Consequently, per Gawker, in 2014: "Wolff filed a matrimonial action against his wife in the Supreme Court of New York"; however, Wolff did not inform his wife whom found out via Gawker. 

Who is Victoria Floethe? Per WagCenter, Floethe is a model (L’Oreal SoColor), an actress (Broken Windows [theater]), a host (LookTV's SEXY. NOT SEXY), a writer (Slate), and she interned at Vanity Fair where she reportedly began her age-gap affair with Wolff. 

And unsurprisingly, per Gawker, Floethe is an (open) teleiophile. Owen Thomas wrote in his Gawker piece, "Victoria Floethe, the New Media Ingénue" (02/26/09), that prior to Wolff, Floethe dated Melik Kayla and Lawrence Osborne - both older (travel) writers. 

The "travel writer" boyfriend whom she never names in the Slate piece is Melik Kaylan, a widely published journalist much older than her. At the time Floethe and he were going out, Kaylan was married. He helped introduce her to Wolff, who got her an internship at Vanity Fair. According to our tipster, to Kaylan's dismay, Floethe switched her affections from Kaylan to Wolff. 

She's also dated Lawrence Osborne, the travel writer ex of founding Gawker editor Elizabeth Spiers. And at an Interview party, she was photographed clinging to the side of English writer Adrian Dannatt.

Lastly, per the New York Times, Wolff's divorce was finally finalized, and he and Floethe are currently married.

Steely Dan's "Hey Nineteen": A Man Declines a Teen's Seduction

 

Steely Dan's "Hey Nineteen" has been popping into my head for years, but not until recently did I have an inclination that the song involved nympholepsy. And my inclination was correct! Per Will Layman's PopMatters post "JAZZ TODAY: The Strange, Mixed Fate of Steely Dan" (10 April 2006): "Gaucho's "Hey Nineteen" was about a middle-aged man's disappointment with a young [19-year-old] lover."

"Hey Nineteen" is track No. 2 on Gaucho (1980), which was Steely Dan's seventh American rock studio album. 

Stewart Mason (incorrectly) posted on AllMusic that "Hey Nineteen" is about man trying to unsuccessfully seduce a "nubile young lass of the titular age".

Hey Nineteen" was the song that finally came right out and told the baby boomers that not only were they not kids anymore, but that the kids of 1980 thought they were a bunch of boring old farts. The song's narrator is with a nubile young lass of the titular age, putting on the same moves that had worked on the sorority girls "way back when in '67" and getting nowhere at all.

However, the song's lyrics make no reference to "the kids of 1980" whom considered the band members a "bunch of boring old farts". The narrator simply shares that in '67, he was a member of Gamma Chi who was privy to "Sweet things from Boston\So young and willing".

Way back when in '67

I was the dandy of Gamma Chi

Sweet things from Boston

So young and willing

And it's posted on SongFacts that the narrator is unsuccessfully attempting to seducing the nymphet. "In this song, an older man is seducing a 19-year-old girl." But that's fiction. 

Boto from 52404 commented: 

I thought if it as more of a 19 year old coming on to him and although he was aware of the age difference, after trying to convince himself it wasn’t a great idea he thought what the hell.

Boto from 52404 is correct, because the chorus is clearly shows that the narrator is rejecting the advances of the teen groupie whom desires to dance and converse with the man.

Hey, nineteen
No, we can't dance together (We can't dance together)
No, we can't talk at all
Please take me along when you slide on down

And after the man discovers that the teen isn't familiar with Aretha Franklin, he double downs on the fact that he is declining her offer to dance and talk. And he adds: "Hey, nineteen\No, we got nothin' common":

Hey, nineteen

That's 'Retha Franklin

She don't remember the Queen of Soul

It's hard times befallen

The sole survivors

She thinks I'm crazy

But I'm just growin' old

Hey, nineteen

No, we got nothin' common

No, we can't dance together

No, we can't talk at all

Please take me along when you slide on down 

Of course, only the nympholepsy naive would opine that a teen groupie wouldn't make an attempt at seducing a much older man. For example, we previously wrote about 16-year-old Nancy Spungen whom, per Lena Dunham's The C-Word podcast (July 8, 2021):

[...] bragged that she had sex with the entire rock group Bad Company but that she only gave hand jobs (simultaneously) to two members of the rock band Aerosmith. In addition, Spungen reportedly had sex with Keith Richards, members of The Who, J. Geils and The Allman Brothers.

Famous Teen Groupie Lori Maddox

And Nikki McWatters shared in the Huffington Post post “Predatory Teenage Girls”:

“Lori Maddox, a famous teenage groupie from LA, is alleged to have lost her virginity to David Bowie at the age of 13. [And] [s]he was [24-year-old] Jimmy Page's steady girlfriend while still underage [i.e., 14-years-old]."

Lastly, per Wikipedia, "Hey Nineteen" was a hit.

"Hey Nineteen" peaked at number 10 on the Billboard Hot 100 chart in early 1981, number 11 on the Adult Contemporary chart, and number 68 on the R&B Singles chart. With a chart run of 19 weeks, "Hey Nineteen" is tied with "Peg" and "Rikki Don't Lose That Number" for being their longest-running chart hit.

"Hey Nineteen" | Lyrics 

Way back when in '67\I was the dandy of Gamma Chi\Sweet things from Boston\So young and willing\Moved down to Scarsdale\Where the hell am I?

Hey, nineteen\No, we can't dance together (We can't dance together)\No, we can't talk at all\Please take me along when you slide on down

Hey, nineteen\That's 'Retha Franklin\She don't remember the Queen of Soul\It's hard times befallen\The sole survivors\She thinks I'm crazy\But I'm just growin' old

Hey, nineteen\No, we got nothin' common\No, we can't dance together\No, we can't talk at all\Please take me along when you slide on down

The Cuervo Gold\The fine Colombian\Make tonight a wonderful thing\(Say it again)\The Cuervo Gold\The fine Colombian\Make tonight a wonderful thing\The Cuervo Gold\The fine Colombian\Make tonight a wonderful thing

No, we can't dance together\No, we can't talk at all

VELMA (2023): Nude Coolsville High Students, DILF City and Teen Lipstick Lesbians!

Per HBO Max: “Velma is an adult animated comedy series telling the origin story of Velma Dinkley, the unsung and underappreciated brains of the Scooby-Doo Mystery Inc. gang. This original and humorous spin unmasks the complex and colorful past of one of America’s most beloved mystery solvers.”

Mindy Kaling executive produced the series, and she played Velma. That news set off our nympholepsy and teleiophilia alarms, which was warranted because, about a minute into the first episode, viewers were entertained by nude nymphets showering in the Coolsville High locker room, which was followed by a nude teen catfight. (Viewers were entertained by the nude showering coeds in episode 10 as well.)

As for teleiophilia, Velma expressed her attraction to (much) older men - more than once. For example, in episode 1, after Fred showed Velma a social media post of his tall and blond father, Velma responded, “Zam, DILF city!”

Oxford Languages: DILF noun | a sexually attractive older man, typically one who has children.

Urban Diction: DILF acronym | "Dad I'd Like to F***".

Toward the end of the first episode, Velma shared that she would like to see a naked picture of LeBron. And in episode 5, in response to learning that Norville was dating Gigi, a cool girl, Velma said, “Damn, this makes me think I could bag Don Lemon.”

As for nympholepsy slash ephebophilia, in episode 2, Velma related that 18-year-old Sarah had a Sugar Daddy, and “Her parents are cool with it.”

In episode 4, at the Crystal Cove Town Hall, Velma unveiled the Top 5 Coolsville High Hot Girls to Mayor Dave whom responded, “Ooh, they are so hot. Daddy likey.”

In episode 8, Daphne shared, “But a while back, I was low-key obsessed with someone […]” What was Velma’s response? “Oh, so like me and Neil deGrasse Tyson.” And in episode 8, Gigi said, “Norville, I wanna go with you to my cabin in the woods [to have sex].” But before Norville could respond, the Coolsville High elderly and balding janitor whispered seductively, “I’ll go.”

In pop culture, nympholepsy is typically coupled with teen lipstick lesbianism. And Velma is no different, as Velma and Daphne, apparent teen bisexuals, had an on-again\off-again affair. (Interestingly, the “hot” Betty and Veronica kiss in the Riverdale pilot was referenced, which was when, in an effort to increase their chances of being picked for the cheerleading team, Veronica passionately kissed Betty in front of the cheerleading captain and her assistants.)

In addition, there were other random bits of salaciousness in the animated series. For example, in episode 1, the owner of Spooner’s Malt Shop, the town’s most popular diner, shared the secret to the diner’s success with Velma: “Just good food, great tunes. And I let teens have sex in the bathroom.”

In episode 6, Daphne and her father dined at Nana’s Nipples - a strip club where Velma’s father pleaded, “Velma please. Can’t a father and daughter just enjoy a nice meal at a strip club without it being awkward?” Subsequently, to the onlookers dismay and despite a neon sign that read 18+ Only, Daphne took to the stripper pole. And in episode 3, while visiting Fred in prison, Velma lifted her fountains and asked Norville, “Is it obvious I have two bean bags in my bra?”

Despite its repeated use of the allure of nymphets for streams, Velma received a measly 41% Average Tomatometer and a 7% Average Audience Score; however, it was (somehow) renewed for second season.

PRETTY LITTLE LIARS: A Student Teacher Sexual Affair Triangle | Alison, Aria & Mr. Fitz

On Pretty Little Liars, Aria and Mr. Ezra Fitz’s age-gap sexual affair may be the most famous (fictional) student-teacher affair in popular culture; however, before Ezria there was Ezrison - the age-gap affair between Alison DiLaurentis and Ezra. And just like with Aria, Ezra met Alison in a bar where, just like Aria, 15-year-old Alison lied about her age; however, unlike Ezria, viewers didn’t learn of Ezrison until season 4.

In “Turn of the Shoe” (s04e02), Tippi, a parrot, parroted “Hey Board Shorts, miss me?", which Tippi learned from Alison. Consequently, the Pretty Little Liars (PLL) learned that Alison had an affair with someone named Board Shorts. 

Alison DiLaurentis

In “Now You See Me, Now You Don't” (s04e12), Aria discovered a letter that revealed that Alison met Board Shorts in Rosewood. In the letter, Alison told Board Shorts that she was planning to take him to her parents' place on the seaside resort of Cape May for her 18th birthday. (Intriguingly, Higbee was the name of Alison’s favorite beach on Cape May, which IRL is a nudist beach.)

Of Rosewood, Alison wrote in the letter to Board Shorts: “It’s best kept secret was you. But you’re my best kept secret now. My friends wouldn’t understand [our age difference].”

Source: Analyzing A\Tumblr

In “Love ShAck, Baby” (s04e15) a PLL noticed an entry in Alison’s journal\dairy titled “Hot for Teacher”, which is also the title of a 1984 Van Halen song that is about a student who is “hot for teacher” . Here’s the text of the letter where Alison expresses her attraction to older men:

Hot for Teacher

I saw a teacher interviewing today with the principal. He was quite sexy. High school boys are gross, college guys are only looking for one thing, but older men, now they know what they want and take it all. He looked kind of bookish but in a cute way. I will get to know him eventually and to have a teacher on my side [...]

In ‘Bite Your Tongue’ s04e17, we learned, via a flashback, that Board Shorts liked to take Alison to The Hart and The Huntsman bar where, after Alison asked Board Shorts, “So, you think I’m mature enough?”, she sensually kissed him.

Alison & Ezra

Eventually, via journal slash diary entries (i.e., Hot for Teacher and The Hart and The Huntsman) and some investigative work, the PLLs discovered that Board Shorts was actually ≈ 22-year-old Ezra.

In “A is for Answers” (s04e24), Alison revealed to Aria that she first met Ezra in a pub that she used to “hangout a lot” in and that she told Ezra that she was a [freshman] at UPenn. (Of course, Alison chose UPenn, an Ivy League school, over Drexel, which would have been just as geographically accurate.)

In a flashback, Alison spied Ezra in the pub, sat next to him, ordered a “gin and tonic”, and foretold Ezra, “Sometimes lies are more interesting than the truth.” Alison went on to share with Aria that Ezra told her that she reminded him of Breakfast at Tiffany’s Holly Golightly and that he wanted her to be the muse for his writing. 

As Ezra was an English teacher and writer, it’s safe to assume that he was referring to Truman Capote's novella and not the film adaptation of Breakfast at Tiffany’s. Of the novella, I related in The Allure of Nymphets that Holly Golightly married a much older man at the age of 13, she lived with a college jock at the age of 15, and at the age of 18, she proclaimed, “I can’t get excited by a man until he’s at least forty-two.”

And Ezra’s Alison slash Holly connection is a double entendre, which will be explored when we discuss Emison. 

Back from the flashback, Ezra exclaimed to Alison, 

“You lied to me.” “Look, it is one thing to make up stories [...] but to lie to a guy and say that you’re 21, when you’re [15 and] still in high school!”

(Note: “you’re 21” may be a Pretty Little Liars continuity error as Alison lied in the letter that she was 18.)

Alison replied, “What’s the big deal? [...]” ''[...] what are you so freaked out about?”

Ezra, “God help me, Alison. I actually like you. I just don’t want to see you get hurt.” 

Allison softly kissed Ezra on the cheek and said, “You’re an alright guy. See you around”

Very interestingly, later in the episode, Alison checked into the Lost Woods Resort under the alias Vivian Darkbloom, which is an anagram of Vladimir Nabokov - the author of Lolita.

If you agree with novelist Robertson Davies' assessment of Lolita, Alison’s use of Vivian Darkbloom as an alias is fitting. We shared in Nymphalis carmen: Nympholepsy in Nabokov’s Oeuvre that Davies opined that Lolita was: “[...] not [about] the corruption of an innocent child by a cunning adult, but [about] the exploitation of a weak adult by a corrupt child.” And Donald Malcolm wrote in his New Yorker piece, “Lo, the Poor Nymphet”: “[...] it is Lolita who boldly, directly seduces him [i.e., Humbert]. 

In "EscApe From New York" (s05e01), Alison took the PLLs to the Fitzgerald Theater in Manhattan. Despite the theater’s “wow” factor, Alison told the PLLs that Ezra didn’t take Alison to the theater to impress her, but that the theater was his, “[...] kind of special place.”  

In a flashback at the theater, once again, Ezra reminded Alison that she was his Holly Golighty.

Upon the stage Alison said, “I could be an actress.”

Ezra, “Could be? Well, I hate to break it to you but you already are.” [...] “You really are my Holly Golighty.”

After Alison learned from Bill, the Fitzgerald Theater’s janitor, that Ezra was in fact a Fitzgerald, she shared with the PLLs that that was when she realized that Ezra was pretending to be poor. Consequently, Alison shared, “I actually like him more for that.” In addition, Alison confessed to the PLLs that she “stayed over a few times” at the theater. Rhetorical question: What was Alison and Ezra doing when she “stayed over a few times” at Ezra's “[...] kind of special place”?

In "Surfing the Aftershocks" s05e03, Alison briefly visited Ezra’s apartment  - only to return his manuscript, but Ezra wanted Alison to let Aria know that she had paid him a visit. One can confidently infer that that was not the only visit Alison made to Ezra’s place. 

Wait, but Ezra wasn’t Alison’s only age-gap affair. Remember when Alison said to Ezra, “What’s the big deal? [...]” ''[...]  what are you so freaked out about?” Well, I left out the part where Alison said, “We didn’t do anything.” That sentence was revealing, because it revealed that Ezra didn’t cause Alison’s teen pregnancy scare. It was Darren Wilden, a Rosewood police officer, who Alison referred to in her journal as Beach Hottie. That’s correct. 15-year-old Alison and 34-year-old Wilden had (unprotected) sex during Alison’s summer break on the romantic seaside resort of Cape May.

As a matter of fact, Alison shared in “Out of the Frying Pan, into the Inferno” (s03e17) that she and Beach Hottie had sex more than once. When asked, “You mean you weren’t using protection?” Alison replied, “We were. Just not all the time.”

Beach Hottie (Darren Wilden), Alison, & CeCe

The PLLs didn’t realize it, but during “Now You See Me, Now You Don't”, they saw a picture of Alison posing on a boat in Cape May with her hand around Beach Hottie’s waist. 

And when Alison was 14, she had an age-gap affair with (approximately) 25-year-old Ian Thomas. Some even considered it one of the hottest hookups in Pretty Little Liars history!

Shyla Watson wrote in her PopSugar post “39 of the Hottest Hookups in Pretty Little Liars History”: “Spencer [a PLL]  isn't the first younger girl who Ian dates in secret. While in a relationship with Melissa [Spencer’s older sister], Ian has a secret affair with a 14-year-old Alison.”

Intriguingly, some PLL fans theorized that Alison's Hot for Teacher journal entry was not written about Ezra but was written about Ian after Alison saw Ian interviewing for Rosewood High’s field hockey coaching position. After which, Alison had a sudden desire to learn how to play the sport. 

Lastly, let’s circle back to Ezra’s double entendre that Alison was his Holly Golightly. 

Rebecca Renner wrote in her The Paris Review post "Was Holly Golightly Bisexual?": "The name Holly Golightly is synonymous with sex and sophistication, but viewers may not know as much about her as they think." You can write that again. Renner then shared this relevant Holly quote from the novella:

“Of course people couldn’t help but think I must be a bit of a dyke myself. And of course I am [...] So what? That never discouraged a man yet, in fact it seems to goad them on.”

And this excerpt from a 1968 Truman Capote Playboy interview is revealing:

Playboy: “Was Holly a Lesbian?”

Capote: “Of course [...] but what intrigues me is the heterosexual male’s fascination with Lesbians.”

What does this have to do with Alison - you may ask? As often is the case with (fictional) teleiophiles, like, Holly, Alison was a lipstick lesbian too who gave Emily, her schoolmate and PLL, “practice kisses”. For example, in a “The Perfect Storm” (s01e09) flashback scene, after Alison read to Emily from Great Expectations, the nymphets kissed in Rosewood High’s library. Consequently, Alison wrote in her journal under the title Girl Crush:

So girl crush kissed me today. To be fair, I kissed her back and it was nice, but I definitely don’t have feelings for her in the way she has for me [...] I catch her staring at me in class [...]

In another flashback, in Rosewood’s locker room, Alison removed her towel, and while topless, she turned to face Emily before she asked Emily if she had seen her new French bra. “Do me a favor. Hook it for me, would you?” Emily obliged and hooked Alison’s French bra, rubbed Alison’s bare shoulder, and kissed Alison's damp neck, which prompted Alison to remind Emily, “Just because we kissed in the library Emily [...] A kiss is a kiss [...] if I’m kissing you it’s because it’s practice for the real thing.”

Alison & Emily

However, in “Miss Me × 100” (s05e05), Alison asked if she could stay in Emily’s bedroom, because her dad was working late, and she didn’t want to go home to an empty house. In addition, Alison informed Emily, “Those kisses just weren’t for practice.” After Emily confirmed with her mom that it was okay for Alison to spend the night, while in bed, Emily aked, “Ali? Are you asleep?” Subsequently, the teens kissed passionately. And fans assumed that they had lipstick lesbian sex! Interestingly, this teen lesbian sex scene was cut from to a student-teacher sex scene with a topless, and presumed bottomless, Aria in the cowgirl position astride Ezra.

There you have it, Alison was a teleiophile who had her first age-gap affair at 14 when she had unprotected sex, multiple times, with an over 30-year-old police officer, and she was a lipstick lesbian. Yet, this raises some questions: Why did the Pretty Little Liars writers make Alison have three age-gap relationships when she had zero in the novels? And why were there multiple references to nympholepsy in the series?  The allure of nymphets.