From historical White House marriages between first cousins, to rumored affairs with celebrities,
to unlikely couples with dramatic weddings, first children have had plenty of odd romantic
tales.
Here are some of the weirdest relationships that presidents' children have had throughout
history.
Theodore Roosevelt's daughter, Alice , was known to be quite the wild child.
She reportedly shocked White House visitors by carrying a small snake (which she named
Emily Spinach) in her purse.
When her father forbid her from smoking under his roof, she climbed up the White House to
smoke above it.
She was also known to have a pillow with the sassy saying, "If you can't say something
good about someone, sit right here by me," in needlepoint.
President Roosevelt reportedly once said,
"I can be president of the United States or I can attend to Alice.
I cannot possibly do both."
She wasn't the typical first daughter, so, of course, she wouldn't marry a typical husband.
Fourteen years older than Alice, Congressman Nicholas Longworth was known to love women
and whisky.
The two, who married in 1906, had an unconventional marriage filled with Longworth's womanizing,
his political rebellion against his wife's father, and the birth of Alice's daughter
Paulina — whose real father was known to be Senator William Borah of Idaho.
And yet, the couple were said to be relatively happy together.
They stayed married until Longworth's death in 1931.
Patti Davis had a reputation of being the rebel of the Reagan family.
She was critical of her father's political policies and didn't share her parents' conservative
style.
She posed nude for Playboy in 1994 and even changed her last name to Davis (her mother's
family name) to set herself apart from her father when she began her acting career.
Though a first daughter might be expected to marry a high-paid politician or a well-known
businessman, Patti rebelled once again by marrying Paul Grilley, her 25-year-old yoga
instructor.
After some rumors about an affair with actor Don Johnson, which Davis denied, the two split
in 1990 after just six years of marriage.
Even before her marriage, Davis was unlucky in love.
She reported a string of disappointing relationships with celebrities, including actors Kris Kristofferson
and Timothy Hutton, as well as Eagles guitarist Bernie Leadon.
She reflected on the relationships to People, saying,
"I went for men who were destined to hurt me emotionally."
Not only did John Adams II, son of John Quincy Adams and grandson of John Adams, marry his
first cousin Mary, but they got together after she dated both of his brothers.
When Mary Catherine Hellen, the cousin in question, was orphaned at age 9, she went
to live with the Adams family.
Mary entered into, and later broke, an engagement with the Adams' oldest son, George.
The youngest brother Charles admitted they also had been together and that she had, quote,
"introduced him to the delights of the flesh."
But it wasn't until middle child John returned to Washington, after being kicked out of Harvard,
when he decided he wanted Mary for himself.
While First Lady Louisa Adams reportedly didn't approve of the match, she did think the two
should be married if they were to be together.
Mary and John had an intimate wedding at the White House, an event both George and Charles,
not surprisingly, refused to attend.
Everyone knows that George W. Bush ended up with Texas native Laura Bush, but not many
realize that Bush almost married another woman first.
Back in the late '60s, he was engaged to Cathryn Lee Wolfman.
The two met during college when Bush was studying at Yale and Wolfman was at Rice.
The early engagement may seem surprising, especially given George's reputation as a
boozing party guy even up until his 30s.
Still, the engagement (and their breakup) made headlines for other reasons.
Wolfman came from a Jewish family, while Bush was a devout Methodist.
Bush has even been known to say publicly, more than once, that those who didn't accept
Jesus Christ wouldn't go to heaven.
Some speculated that Bush's family, with their differing religious beliefs, could have broken
up the engagement, though this was never confirmed.
Today with Hoda & Jenna co-host Jenna Bush-Hager met her now husband, Henry Hager, back in
2004.
While the two may seem to make a good match now, the high-profile couple had a rocky beginning.
When they first met, 26-year-old Hager was actually George W. Bush's employee.
While it may have already been a bit scandalous for Jenna to date someone on the staff, to
add to the drama, she revealed on an episode of Today that her now-hubby already had a
girlfriend at the time.
"I don't always tell people this — I turn really red when I do — but he worked for
my dad."
"He did?"
"It's so embarrassing."
"Oh, I didn't know that."
"And he had a girlfriend."
"He did?"
Early on, there were doubts about Jenna and Hager's relationship, with concerns coming
most notably coming from Jenna's mother, Laura Bush.
When asked about the relationship back in 2005, Laura publicly said of Hager,
"This is not a serious boyfriend.
I hate to have to be the one to say it on television.
But he's a very nice young man."
Despite the odds, the naysayers, and the early girlfriend drama, the pair got married in
2008, had children, and are still together.
The Bush twins were notorious for their partying and underage drinking back when their father,
George W. Bush was in office.
While Barbara eventually settled down and married screenwriter Craig Coyne in October
of 2018, back in 2015, she reportedly dated a guy in the ping-pong industry.
Yes, that's right — there's an industry for ping-pong.
Her one-time boyfriend Franck Raharinosy didn't just have an uncommon vocation; he also had
a reputation as a womanizer.
In an Observer profile from 2009, Raharinosy's business partner said,
"Franck can't be stopped.
He's the type of dude who's going to meet a girl at a club and make out with her — or
have sex with her in the bathroom."
The party guy and playboy might have been an accepted fixture during Barbara's time
when she was "young and irresponsible" — a term her father used to explain his own wild
years — but it made for a surprising match for the 33-year-old Bush twin.
Not surprisingly, the relationship didn't last.
John Van Buren, son of 8th president Martin Van Buren, was a lawyer, a politician, and
an advisor to his father.
However, he was also a known drinker, gambler, and womanizer.
This caused much concern, especially after Martin Van Buren was elected president.
President Van Buren reportedly once wrote a letter to his son asking him to change his
ways, saying,
"I was informed that you had been twice carried drunk from the race course."
Van Buren's addiction reached an all time low when he reportedly lost his mistress,
Elena America Vespucci, in a bet.
According to lore, Vespucci was with Van Buren one evening when John apparently found himself
on a losing streak.
He was down $5,000, and, desperate to win his money back, Van Buren offered up Vespucci.
Van Buren lost, and Vespucci ended up living with her new beau, the game's winner, for
years.
Before marrying Jared Kushner in 2009, Ivanka Trump had a few other noteworthy beaus.
Topher Grace, of That '70s Show fame, confirmed to People in 2018 that he and Ivanka dated
for a short time back in 2006.
He said of their short time together, quote, "Certainly, it wasn't a political statement,"
pointing out that their relationship took place long before Donald Trump's political
career.
"No offense, Donna, but dude, you're on fire!"
Before dating Grace, Ivanka was linked with Lance Armstrong.
A source told People back in 2006 that the two went on several dates, but apparently
nothing came of it.
Ivanka told the outlet,
"I have tremendous respect for Lance and all he has accomplished.
That said, we are just friends."
Quincy Jones also claimed to have gone on a date with Trump, who is 48 years his junior,
before she married Kushner.
He explained, in an interview with Vulture, that Tommy Hilfiger played matchmaker, telling
Jones that Ivanka wanted to have dinner with him.
However, Ivanka never confirmed this, and a source close to her told E! News that "this
story is not true."
In March 2018, Donald Trump Jr. made headlines with news of his divorce from Vanessa Trump,
his wife of 12 years and mother of their five children.
Around that time, rumors were flying about an alleged affair with Celebrity Apprentice
cast member Aubrey O'Day back in 2011 and 2012.
Us Weekly confirmed the news with multiple anonymous sources and reported that the two
met while filming his father's reality series.
A source told the outlet,
"He told her it was over with his wife, that they were separated and he didn't love her
— all of that stuff.
Aubrey fell for him hard."
Trump Jr. stopped seeing O'Day in 2012 when Vanessa allegedly found emails between her
husband and O'Day, Us Weekly reported.
For years after the alleged affair, Vanessa and Trump Jr. stayed together and even had
two more children together, but it was only a matter of time before the two would call
it quits.
It's certainly a national affair when a president's child gets married.
But what if the happy couple consists of not one, but two presidential offspring?
This was the case when Richard Nixon's daughter, Julie, married Dwight Eisenhower's grandson,
Dwight "David" Eisenhower II.
The wedding was set for December 1968, but when Nixon was elected just weeks before his
daughter's big day, he prompted Julie to hold the ceremony at the White House.
Getting married at the White House was, as Nixon wrote in his 1979 memoir, a "unique
privilege."
In fact, only 15 other couples in U.S. history had done it.
However, Julie refused the opportunity.
Despite both her and her fiancé's presidential lineage, the couple didn't want politics involved
in their wedding.
Instead, they wed in a nondenominational church in New York City.
In 2018, The Washington Post reported that the two were still married after 50 years.
When Woodrow Wilson's youngest daughter, Eleanor Wilson, first met William Gibbs McAdoo, he
was visiting the family at the governor's mansion in New Jersey.
According to the book All the Presidents' Children by Doug Wead, Wilson was reportedly
so nervous around him that she spilled cream, and almost spilled his coffee, at breakfast.
By the time Wilson's father was elected president, McAdoo was actively pursuing her, despite
her already being secretly engaged to another man.
What's more, the two had a 26-year age difference.
McAdoo, who was already a father and a grandfather, had six children, one of whom was about Wilson's
age.
Despite these hurdles, Wilson and McAdoo became the 12th couple to be married in the White
House in May 1914.
The unlikely lovebirds seemed to have a successful marriage for some time, having two daughters
and staying together for 20 years.
However, the two eventually called it quits and divorced in 1934.
Though John F. Kennedy Jr. famously married blonde beauty Carolyn Bessette in 1996, he
had a well-documented dating life before settling down.
One of his former loves was actress Daryl Hannah.
According to J. Randy Taraborrelli's book, The Kennedy Heirs, Kennedy's mother, former
first lady Jacqueline Kennedy Onassis, reportedly didn't approve of Hannah — and the objection
made Kennedy want to be with Hannah even more.
Interestingly, Hannah wasn't the only girlfriend Onassis didn't approve of.
It's reported that she also wasn't a fan of Madonna, to whom Kennedy was connected for
a short time in 1988.
As Christopher Anderson wrote in his book, The Good Son: JFK Jr. and the Mother He Loved,
"There were many things about Madonna that rubbed Jackie the wrong way."
Kennedy also dated Sarah Jessica Parker, of Sex and the City fame, in 1991.
The New York Times reported that Parker thought dating the former first son was an enjoyable
experience, though the press she received during that time was overwhelming to her.
She recalled,
"We would go places where there wasn't a soul around, and the next day I'd see pictures
of us there in the tabloids."
Back when Camilla Parker Bowles was first dating Prince Charles, her brother, Mark Shand,
was with a former first child.
According to the book American Legacy: The Story of John and Caroline Kennedy by C. David
Haymann, Shand and Caroline Kennedy met in 1972, and hit it off right away.
U.K. native Shand introduced Kennedy to a fine-art program in London, and she enrolled.
When Kennedy arrived in London, she found that Shand was with another woman: American
actress Barbara Trentham.
Shand, however, soon broke it off with Trentham, and he and Kennedy started dating.
According to American Legacy, Kennedy was supposedly in love with Shand.
She even refused to return to the U.S. when her mother insisted, as reported in Christopher
Wilson's book, The Windsor Knot: Charles, Camilla, and the Legacy of Diana.
But at the end of her studies, Kennedy finally returned home, and she and Shand broke up.
In 1986, Kennedy married her current husband, Edwin Schlossberg, in Cape Cod.
Hunter Biden, the son of President Joe Biden, has often made headlines for his drug and
alcohol addictions, but his relationship with his sister-in-law has also gotten him noticed.
Hunter met his future wife Kathleen when he was working as a Jesuit volunteer at a church
in Portland, Oregon.
After just three months of dating, Kathleen became pregnant, and the two married in 1993.
The couple had three children together, but by 2016, the couple had split and Kathleen
had filed for divorce.
Meanwhile, after the tragic death of Hunter's brother, Beau Biden, from brain cancer in
May 2015, Hunter and Beau's widow, Hallie, became close.
The two texted "constantly," The New Yorker reported, and Hunter even started spending
nights at Hallie's house in Delaware.
Hunter told The New Yorker.
"We were sharing a very specific grief.
I started to think of Hallie as the only person in my life who understood my loss."
By 2017, Hunter and Hallie were officially a couple, dating for two years until they
split in 2019, as reported by Page Six.
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