Presidential Children Who Got Into Weird Relationships

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The president's children are often seen as American royalty. The press reports on which schools — and which parties — the first children attend, their pictures pop up on the cover of magazines and in the pages of tabloids, and the nation watches eagerly when their romantic relationships blossom (and when they fall apart). 

Perhaps the American people are so interested in the relationships of the first children because these presidential offspring sometimes choose strange partners. While one might assume the president's son or daughter would have the highest standards for their romantic interests, many of their picks are surprising, if not downright weird. 

From historical White House marriages between first cousins to rumored affairs with celebrities, to unlikely couples with dramatic weddings, it seems like there's always an odd romantic tale coming from a former, or current, first child. Here are some of the weirdest relationships that presidents' children have had throughout history.

Wild child Alice Roosevelt married a White House aide 14 years her senior

Theodore Roosevelt's daughter, Alice (1884-1980), 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.

Ronald Reagan's daughter Patti Davis married her yoga instructor

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. "I went for men who were destined to hurt me emotionally," she told People.

John Adams II kept it in the family

Not only did John Adams II (1803-1834), 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 "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. 

George W. Bush was engaged before he met Laura

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. It was even made official with an announcement (and a photo of the happy couple) in the Houston Chronicle on Jan. 1, 1967 (via Houston Press). 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.

Jenna Bush married her father's employee, who had a girlfriend when they met

Today with Hoda & Jenna co-host, and notorious Bush twin, 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, according to The Washington Post. 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.

Early on, there were doubts about Jenna and Hager's relationship, concern 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" (via The Washington Post). Despite the odds, the naysayers, and the alleged girlfriend drama at the beginning, the pair got married in 2008, had children, and are still together.

Barbara Bush dated a guy in the ping-pong business

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.

It might come as a shock that Barbara would date anyone out of the family business of politics, but especially shocking that her one-time boyfriend Franck Raharinosy had such a bad 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 since-tamed Bush twin. Not surprisingly, the relationship didn't last.

Martin Van Buren's son John gambled away his mistress

John Van Buren (1810-1866), 8th president Martin Van Buren's son, 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.

Ivanka Trump was romantically linked to a small handful of surprising celebrities

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. "Certainly, it wasn't a political statement," he said of their short time together, pointing out that it was long before Donald Trump's political career.

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. "I have tremendous respect for Lance and all he has accomplished," Ivanka told People. "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."

Donald Trump Jr. allegedly had an affair with a Celebrity Apprentice contestant

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. "He told her it was over with his wife, that they were separated and he didn't love her — all of that stuff," a source told Us Weekly. "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.

Julie Nixon married Dwight Eisenhower's grandson and wanted a non-political wedding

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, The Memoirs of Richard Nixon (via The Washington Post), 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. Nixon wrote in his memoir (via The Washington Post), "Both she and David felt that they wanted their wedding ceremony to be as personal and non-political as it possibly could." 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.

Nellie Wilson married a grandpa in his 50s

When Woodrow Wilson's youngest daughter, Eleanor (Nellie) 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, according to the book Best Little Stories from the White House: More than 100 True Stories by C. Brian Kelly. 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. According to reporting by The Washington Post, 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.

JFK Jr. dated Madonna, Daryl Hannah, and Sarah Jessica Parker

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 (via People), 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 told The New York Times, "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."

Caroline Kennedy dated Camilla Parker Bowles' brother

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. At the end of her studies, Kennedy finally returned home, and she and Shand broke up. In 1986, Kennedy married Edwin Schlossberg in Cape Cod, and, at the time of publishing, the two are still together and have three children.

James Monroe's daughter married her cousin

President James Monroe's daughter, Maria Hester Monroe (1803-1850), made history when in 1820 she and Samuel Lawrence Gouverneur became the second couple to be married at the White House. 

While her wedding was certainly noteworthy, Maria's choice in husband was perhaps an odd one. As reported in Doug Wead's book, All the Presidents' Children, Maria's husband, 21-year-old Gouverneur, worked for her father as one of the "junior" White House secretaries — he was also the bride's first cousin.

But it was the wedding itself, not the couple, that would cause scandal. Maria's sister, Eliza, and their mother, First Lady Elizabeth Monroe, took over the planning of the event, and intentionally didn't invite key diplomats and cabinet members to the wedding. This was seen as a slight and caused a social scandal in Washington. Eventually, arrangements were made, likely by Monroe himself, for additional wedding receptions that political guests could attend. Unfortunately, Eliza and her mother managed to change the guest list for these events as well and the wedding scandal continued.

Hunter Biden dated his brother's widow

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 Biden (née Buhle) when he was working as a Jesuit volunteer at a church in Portland, Ore., according to The New Yorker. 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. "We were sharing a very specific grief," Hunter told The New Yorker. "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.