The Tackiest Romantic Gestures MAGA Men Have Ever Made

MAGAland is for — lovers? There's no shortage of romance among the members of Donald Trump's inner circle, but it can sometimes feel like we're watching their love stories unfold through the lens of David Lynch's camera. One day a MAGA-ite is kissing the ring at the White House, and the next, they're kissing their sweetie at one of Donald's bizarre Mar-a-Lago parties as dancers wearing dog head masks and 18th-century court dress swirl by. And MAGA men's romantic gestures can get just as weird as the "Let them eat kibble!" goings-on at the so-called "Winter White House."

If you're one of the MAGA elite planning a wedding, you'll probably feel obligated to get hitched at Mar-a-Lago or another Trump property. And if you're really lucky, the MAGA king might verbally bless your union. During his daughter Tiffany Trump's Mar-a-Lago wedding toast, Donald ranted about money, telling guests he refused to rent a tent because it cost too much.

Donald also gave a speech at the wedding of political advisor Stephen Miller and podcaster Katie Miller, who had an Elvis Presley impersonator at their Trump International Hotel nuptials. Of course, Donald made the moment about himself, as he is wont to do, by complaining, "He is the only one who could have a damn wedding in the middle of Presidents' Day weekend. I'm sure it didn't affect anybody here" (via Vanity Fair). Sadly, the president's attempts at romantic gestures for his wife, Melania Trump, are worse than his wedding speech content.

Kisses shared between Donald Trump and Melania Trump expose their relationship as one that seems to lack a lot of passion. But there's something that motivates Donald to get in touch with his romantic side: money. In February 2024, his supporters received a special Valentine's Day message addressed to Melania in their inboxes. "Dear Melania, I LOVE YOU! ... Even after every single INDICTMENT, ARREST, and WITCH HUNT, you never left my side," it read in part (via HuffPost). The email came from Donald's joint fundraising committee, so its main aim wasn't to hype up Melania but to convince recipients to donate $47 to Donald's campaign to become America's 47th president.

Melania probably also wasn't too impressed with where her husband chose to wish her a happy birthday a few months later: at the courthouse where Donald was on trial for concealing hush money payments to Stormy Daniels. "We're doing very well in this rigged trial. Everybody knows it. Yesterday was a big day, but I do have to begin by wishing Melania happy birthday," he said, per Metro. 

He didn't go out of his way to make Melania's birthday special in 2018, either. Months after the story broke about Donald allegedly cheating on his wife with Daniels, he appeared on "Fox & Friends" and was asked about his birthday shopping. "Maybe I didn't get her so much ... I got her a beautiful card," he said. "I'm very busy to be running out looking for presents, okay?" At least he didn't get Melania lingerie, sparing her the humiliation of sharing intimate revelations about her intimates — like he did during a 2025 rally when he said that she steams her underwear.

Calling Donald Trump "Daddy" isn't the worst thing Fox News host Jesse Watters has done. The MAGA mouthpiece is among the many celebs who allegedly cheated with younger partners; in 2018, Noelle Watters filed for divorce after learning that Jesse was having an affair with then-25-year-old Emma DiGiovine, another Fox News employee. Drawing attention to your cheating scandal is something most news hosts would likely steer clear of, but in 2022, Jesse regaled "The Five" viewers with a train wreck of a tale about how he wooed his now-wife.

What was apparently a sweet love story for Jesse began with a horror movie opening that would make many women's hearts stop. "When I was trying to date Emma, the first thing I did, I let the air out of her tires," he recalled. "She couldn't go anywhere." He then came to her rescue by offering her a ride. Jesse informed his co-hosts that DiGiovine had remained blissfully unaware that his chivalrous act was actually a deceitful scheme until his on-air revelation, which had Greg Gutfeld comparing him to "the Zodiac Killer." And when Jeanine Pirro asked if he had tried the skeevy stunt before, all he would say was, "It works like a charm."

Jesse Watters jokes about how he courted a woman 14 years his junior. He let the air out of her tires so he could offer her a ride home. He leaves out that he was married at the time. This is some stalker nonsense. She also worked for him. It's a Fox News love story pic.twitter.com/ge9zZ2vMMH

— Decoding Fox News (@DecodingFoxNews) April 16, 2022

Social media users found Jesse's story disturbing and gross, and he attempted to take it back days later by telling Fox News viewers he had been joking (via People). Whether this was just damage control or his anecdote really was a creepy attempt at comedy, the damage was already done; years later, it was still giving netizens the ick.

The Empire State Building isn't the most original location to propose, but because Jeanette Rubio is a fan of the Tom Hanks and Meg Ryan rom-com "Sleepless in Seattle," it's where Secretary of State Marco Rubio decided to ask her to marry him. He also chose the cliche date that plays an important role in the film. Unfortunately, what the Florida native didn't account for was how cold New York City can get on Valentine's Day.

Jeanette didn't want to visit the Empire State Building's observation deck because of the chilly weather, so Marco had to pretend it had always been his dream to be large enough to scurry up the skyscraper with a terrified Fay Wray screaming from his golf cart-sized fist. "I told her, 'I love King Kong. I've always wanted to climb the Empire State Building!'" he recalled to Parade. While the ploy worked, Jeanette was still reluctant to play the damsel in distress role. "I was like, 'Seriously, Marco?'" she told the magazine.

On "The Tonight Show," Marco admitted that the temperature that day was only in the 40s, but perhaps it still had Jeanette shivering hard enough that he feared her engagement ring would meet the same fate as the giant ape he had pretended to adore. "I thought she was going to drop the ring off the side, so I grabbed the ring back, and then I gave it back to her at the bottom," he recalled. But why wait that long and leave poor, freezing Jeanette to wonder whether he was having second thoughts during the elevator ride back down?

Far from a fairytale romance, Donald Trump Jr. and Bettina Anderson's MAGA love story unfolded more like a farcical tragedy. If Shakespeare were alive today, perhaps he'd find inspiration in Kimberly Guilfoyle's brutal rise and fall. While Guilfoyle was still attending public events with the man she was supposed to be marrying — sometimes with Anderson there — she had to watch the press catch wind of his blossoming romance with the younger socialite. And as Anderson and Trump Jr.'s relationship grew serious, the president, who almost became Guilfoyle's father-in-law, decided to send her off on a new adventure in Greece, keeping her far from her erstwhile fiancé.

We got some insight into how Trump Jr. wooed his new ladylove in December 2024 when Anderson shared a photo of what was believed to be a birthday card from her beau on her Instagram Story. "Many have said you're aging out but I think you're perfect ... happy birthday!" it read (via the Daily Mail). Anderson had just turned 38, whereas Trump Jr. was 46. Still, he resides in a political sphere populated by men who listen to the likes of the late Charlie Kirk, who once described women over 30 as "not at their prime" during a Turning Point USA event.

Anderson's Instagram reaction to Trump Jr.'s birthday message fixating on her age read, "Tough but fair." According to Radar, she had a reason for putting up with his negging. Insiders told the webloid she was hoping to use him to gain access to "bigger fish," including billionaire Elon Musk.

Dr. Mehmet Oz's romance with his future wife, Lisa Oz, got off to a bumpy start. "Lisa is a vegetarian, and when we first met, I had no idea what that was. I took her to a cheesesteak place on our first date!" Dr. Oz told Woman's Day in 2012. Yes, the man who would become a health guru backed by Oprah Winfrey once thought vegetarians would be totally down with chowing down on beef. But it gets weirder.

In a 2018 interview with Yahoo! Life, Dr. Oz joked that he and Lisa had an "arranged marriage" because they met through their fathers, who were friends with each other. But they didn't decide to actually get married until a few months into their relationship. "We got into a big fight, and I realized I couldn't live my life without Lisa," Dr. Oz recalled. To let her know how serious he was about never letting her go, he popped the question with a pull tab that he found on the street. His impulsive proposal with a piece of trash was successful, but apparently, that lovers' quarrel would set the tone for the rest of their marriage. "We fight — a lot," Lisa said to Shape in 2011.

While their journey to the altar started with Dr. Oz sliding some garbage on his bride-to-be's finger, the future CMS administrator would discover that navigating life as a married man is more like unclogging a toilet than doing a little recycling. In a 2019 Facebook post, he shared this sage advice: "Marriage is messy, so bring a plunger."

When Texas Senator Ted Cruz tied the knot with Heidi Cruz in 2001, she found one of his wedding demands rather confounding: that they play a CD recording of the song "A Whole New World" from the Disney movie "Aladdin" instead of having the band they hired perform it. The couple also didn't share the same view of the romantic song's message, which Ted hoped would be reflected in their future together in a positive way. "He'll be like, 'It's such a great life! We have so much adventure ahead! It's like our magic-carpet ride,'" Heidi told The Atlantic in 2018. "And sometimes I'm like, 'I hope we don't hit the cement.'" For her, it's "a whole new world, a new brutalist point of view."

At least Ted didn't also insist that they forgo catering and serve their guests oodles of noodles and broth instead. During a 2016 CNN town hall, Heidi revealed how she learned that her husband will happily slurp his supper down for days. "We got back from our honeymoon, and he went off to the store and came home by himself," she recalled (via Gawker). "And I was completely shocked to see that he arrived back at our apartment with literally 100 cans of Campbell's Chunky soup." 

According to Heidi, when she tried to tell Ted that they would not be subsisting on his soup stash while settling into married life, he said to her, "I know you. You won't be making things." His perplexing purchase could either be construed as a thoughtful gesture meant to save his wife from the hassle of cooking or a passive-aggressive way to trash her homemaking skills. Either way, it was downright weird.

Long before she co-chaired the Republican National Committee, hosted a Fox News show, or butchered a Tom Petty classic, Lara Trump was a pastry chef who had her own cake company. On her YouTube series "The Right View," she revealed that she was studying at the French Culinary Institute when she first met Eric Trump at a New York nightclub. She dropped this tasty tidbit of information during their introductory conversation, but Eric wasn't impressed. "He grabbed my side, and he was like, 'I bet all of your cooking tastes like garbage because it doesn't seem like you've been eating any of it,'" she recalled.

Instead of being creeped out by a guy who, in one fell swoop, managed to trash her cooking, weight shame her, and feel her waist to see how slim it was, Lara was intrigued. She explained that this was because Eric didn't react to her culinary school revelation the way most men did, which typically entailed suggesting that they "cook together sometime." But who needs to sweat over a hot stove when you're a Trump? During another episode of "The Right View," Lara explained why Eric asked his mother, Ivana Trump, to join them for one of their early dates. "He basically was like, 'Let's invite my mom to dinner because I want to make sure that we go to a place that's nice enough, but if we invite her, she'll pay for it,'" she recalled. At least he was honest about his motive.

Donald Trump Jr. has plenty of practice popping the question now, after doing it three times, but in 2004, he was a newb to the whole fiancé game when he got down on one knee and asked Vanessa Trump (née Haydon) to do him the honor of marrying him. Unfortunately for the heir, he made a rookie mistake by reportedly proposing in front of a jewelry store at a mall in exchange for a free ring. 

The New York Post called Donald Jr. out for being cheap when it reported on how he procured Vanessa's $100,000 engagement ring from Bailey, Banks & Biddle, which apparently isn't a Diagon Alley shop J.K. Rowling conjured up to sell magic baubles to witches and wizards. When CNN host Larry King asked Donald Trump to weigh in on his son's stunt on "Larry King Live," he confessed, "I wasn't thrilled with what he did to be honest with you."

Apparently, Donald Jr. learned his lesson. When he got proposal redos with Kimberly Guilfoyle and Bettina Anderson, he kept them private affairs and didn't invite the paparazzi. However, he did propose to Bettina — who is pals with Vanessa — at Camp David with an eight-carat ring designed by jeweler Sue Gragg. The Daily Mail consulted with jewelry expert Roy Albers, and he estimated its value to be as much as $800,000. Of Guilfoyle's ring, Albers said, "The amount he paid was likely between $200,000 and $300,000."

Before "Curb Your Enthusiasm" star Cheryl Hines learned to stop worrying and love the MAGA movement, her husband's political career was likely giving her whiplash. First, Robert F. Kennedy Jr. announced that he was running against Joe Biden as a Democrat in April 2023. When this endeavor proved to be futile, he decided to run as an Independent instead that October. He then switched political allegiances a third time when he abandoned his presidential bid altogether in August 2024 and endorsed Donald Trump. Of how his wife felt about the move, RFK Jr. told TMZ, "She's a lifelong Democrat, and the idea of me supporting Donald Trump ... it's something that she would have never imagined."

RFK Jr.'s behavior was making life hard for Hines, as she later revealed." Some people were very upset that I was even married to Bobby. They were vocally coming at me because I'm married to Bobby," she told Fox News in October of 2025. "So, Bobby felt like, 'You shouldn't be having to take that heat. So, why don't we just say we're separated?'" While Hines rejected this idea, she did say that she found it "sweet."

Now, let's rewind to September 2024, when news of RFK Jr.'s affair with reporter Olivia Nuzzi broke out. Sources claimed that it had started in early 2024, when RFK Jr. was still campaigning for president and wreaking havoc on Hines' social life. Knowing all of this, some might not agree that it was "sweet" to advertise that he was single when he was not, especially considering that RFK Jr.'s long list of rumoured affairs.

White House Deputy Chief of Staff Dan Scavino got engaged to Erin Elmore, a State Department official and former contestant on "The Apprentice," in September 2025. When recounting the romantic moment to Lara Trump for her Fox News show, "My View," Scavino said that he let Donald Trump know he was about to pop the question and joked that it felt like he was asking Elmore's father for his blessing. "I said, 'Sir, do you mind if I get engaged this evening?'" he recalled. Donald didn't just give Scavino the go-ahead; he picked the spot outside the White House where he wanted to see the proposal happen, and he even pointed to where a videographer could set up a camera to capture the moment.

Scavino shared the results of his boss's input on Instagram, and it was a poorly staged production. There was no way Elmore didn't know what was coming, as Scavino made her stand with her back to him for what seemed like an eternity while he got down on one knee. Her almost-hyperventilating reaction was also major overkill.

Scavino and Elmore's February 2025 Mar-a-Lago wedding was just as tacky, thanks in part to the guest list: Karoline Leavitt, Pam Bondi, Fox News couple Ainsley Earhardt and Sean Hannity, Elon Musk, as well as Kristi Noem and her rumored lover, to name a few. Photographs from the event also featured a MAGA-style hat honoring the event's VIP attendee. "Trump Made this Happen," it read.