Jerry Seinfeld's wife Jessica shares a rare family photo from youngest son Shepherd's high school graduation (but one detail leaves fans VERY surprised)

Jerry Seinfeld's wife Jessica took to Instagram on Tuesday to share a rare family photo from their youngest son Shepherd's high school graduation.

The author, 52, was a proud mom as she posed alongside the 18-year-old graduate, as well as her comedian husband, 70 — whose comments about PC comedy were recently deemed a 'red flag' by a former co-star — daughter Sascha, 23, and older son Julian, 21. 

Fans also noted one detail that left them surprised about the snap - the teenager was casually holding a lit cigar in his hand. 

Jessica went on to share an image of her son and his pals celebrating together, with a number of them also smoking cigars. 

The mom-of-three wrote a lengthy caption, sharing that she and Jerry gave Shepherd a flip phone as his graduation gift. 

Jerry Seinfeld's wife Jessica, 52, shared a rare family photo from their youngest son Shepherd's high school graduation on Tuesday, where she was also joined by her husband, 70, daughter Sascha, 23, and older son Julian, 21

Jerry Seinfeld's wife Jessica, 52, shared a rare family photo from their youngest son Shepherd's high school graduation on Tuesday, where she was also joined by her husband, 70, daughter Sascha, 23, and older son Julian, 21

Fans also noted one detail that left them surprised about the snap - the teenage graduate was holding a lit cigar in his hand

Fans also noted one detail that left them surprised about the snap - the teenage graduate was holding a lit cigar in his hand

'Our youngest son Shepherd graduated from high school yesterday. As I posted earlier in my stories, we gave him a flip phone for graduation in hopes he will turn in his smartphone.'

'Many of you have asked if this is his first phone - I wish! If I knew then what I know now, I would've waited until age 14 to give him a smartphone (he got handed down an old one at age 12, for the bus ride to school in the Bronx).'

'In the last two slides is a phone my friend Lisa just told me about @thelightphone. Very curious about this - does anyone have one?'

Jessica looked summer-ready in the snap, wearing a vibrant pink dress. Her blonde hair was pulled back into a ponytail.

Jerry looked handsome in a suit and a polka dot tie. 

He shielded his eyes with a pair of sunglasses and flashed a bright smile as he stood in the middle of his kids looking every inch the proud dad. 

Sascha opted for a green dress, while Julian looked dapper in a navy button-up and black pants. 

In 2020 Jessica shared that Jerry wasn't a 'natural' when his first child was born.

'He wasn't immediately pushing strollers and carrying babies. He jokes that it took him a good 10 years to warm up,' she told Parents magazine. 

She added that things turned for the better when the kids became teenagers.

Jessica also shared an image of her son and his pals celebrating together, with a number of them smoking cigars

Jessica also shared an image of her son and his pals celebrating together, with a number of them smoking cigars

The mom-of-three wrote a lengthy caption, sharing that she and Jerry gave Shepherd a flip phone as his graduation gift

The mom-of-three wrote a lengthy caption, sharing that she and Jerry gave Shepherd a flip phone as his graduation gift

In late April Jerry was joined by his family during the premiere of Unfrosted, which took place at the Egyptian Theatre in Hollywood

In late April Jerry was joined by his family during the premiere of Unfrosted, which took place at the Egyptian Theatre in Hollywood

Jessica and Jerry also made a stylish duo at the Met Gala in New York in May (pictured)

Jessica and Jerry also made a stylish duo at the Met Gala in New York in May (pictured)

The couple have been married since 1999. They met during her first marriage to Eric Nederlander, a scion of one of New York's top theater-owning dynasties; Seen in 2019

The couple have been married since 1999. They met during her first marriage to Eric Nederlander, a scion of one of New York's top theater-owning dynasties; Seen in 2019

'Jerry's strength is now, with our three teenagers. He's patient with them. Where I am weaker, he is stronger, and we complement each other. I wouldn't change anything.'

In late April Jessica and all three kids were there to support Jerry at the premiere of his new Netflix movie, Unfrosted. The family happily posed together on the red carpet.

Jerry and Jessica have been married since 1999.

The couple met during her first marriage to Eric Nederlander, a scion of one of New York's top theater-owning dynasties.

She insisted in the New York Times that she initially displayed no interest in Jerry, who was supposedly unaware she was married when he first tried flirting with her.

Eric however furiously accused Jessica of cheating on him with Jerry, and filed for divorce in late 1998 just four months after the wedding.

'I was manipulated, misled, and completely caught off guard by Jessica’s infidelity,' he fumed to Page Six. 'Jerry and Jessica have no respect for decent values. They deserve each other. I’m going on with my life.'

The following year, Jessica and Jerry tied the knot in a Christmas Day ceremony officiated by the comedian George Wallace.

Jerry recently sparked pushback with his comments about how politically correct comedy has gotten in more recent years.

Julia Louis-Dreyfus recently disagreed with Seinfeld's comments about comedy turning too politically correct on television, which he blamed on 'the extreme left and PC crap'
Jerry cited some of the classic sitcoms when making his point about political correctness and its effect of television

Julia Louis-Dreyfus recently disagreed with Seinfeld's comments about comedy turning too politically correct on television, which he blamed on 'the extreme left and PC c**p' 

The duo famously starred together for the entirety of the sitcom Seinfeld. The show ran for nine seasons, airing from 1989 to 1998; They are pictured in a still

The duo famously starred together for the entirety of the sitcom Seinfeld. The show ran for nine seasons, airing from 1989 to 1998; They are pictured in a still

Julia Louis-Dreyfus argued against her former Seinfeld co-star's belief that 'the extreme left and PC c**p' is ruining comedy on television, adding that political correctness can actually be 'fantastic', during an interview with the New York Times.

'When I hear people starting to complain about political correctness — and I understand why people might push back on it — but to me that's a red flag, because it sometimes means something else,' Louis-Dreyfus, 63, told the publication. 'I believe being aware of certain sensitivities is not a bad thing. I don't know how else to say it.'

Seinfeld vented about the lack of comedies on television due to people worrying so much about offending other people in an interview with The New Yorker in late April.

'It used to be, you would go home at the end of the day, most people would go, "Oh, Cheers is on. Oh, M*A*S*H is on. Oh, Mary Tyler Moore is on. All in the Family is on." You just expected, there'll be some funny stuff we can watch on TV tonight,' he told the publication. 'Well, guess what — where is it? This is the result of the extreme left and P.C. c**p, and people worrying so much about offending other people.'

Jerry also made headlines recently after stating that he misses the era of 'dominant masculinity' in American pop culture and society.

Jerry and Julia famously starred together for the entirety of the sitcom Seinfeld. The show ran for nine seasons, airing from 1989 to 1998.