Is This the Worst Engagement Location Ever?
Quick, what is the cringiest engagement scenario you can think of? Flash mob? Jumbotron at a baseball game? The ring was in your dessert and you accidentally ate it? Horrors all around, but I have a new one that you might not have even considered. What if your boyfriend was so obsessed with his boss that he asked you to marry him right outside of the big man’s office? Well, that’s how President Donald Trump’s deputy chief of staff, Dan Scavino, went about proposing to his girlfriend Erin Elmore.
If you’re wondering who these people are, that’s a great question. Scavino is a longtime Trump aide who first rose to prominence as the president’s Twitter scribe during his first term. He met Trump as a teenager working as a golf caddie and later became the manager of the Trump National Golf Club Westchester. Elmore was on The Apprentice in 2005 and has been in Trump’s political orbit since 2016, when she was a campaign surrogate. She’s currently the director of art in embassies at the State Department, the kind of fake-ish job they give you if you’re loyal but not important enough for an ambassadorship to one of the fun European countries. This will be a second marriage for both of them. Scavino got divorced in 2018, while it’s unclear when Elmore split from her former husband (she was wearing her wedding ring as of last October).
But back to the proposal. Scavino announced the news on Wednesday with a very sleek video of him popping the question with a predictably enormous ring set to the perfect royalty-free ballad. Roll the tape.
She said YES❤️???????????????????? pic.twitter.com/BMrWvZbvpN
— Dan Scavino Jr.???????????? (@DanScavino) September 25, 2025
Wow, she looks so shocked. Perhaps Scavino is always leading her on walks around the White House grounds with a cameraman nearby and then asking her to turn around and look at something else for a little bit while he gets situated.
As for the location, it does leave something to be desired. It appears that they’re just outside of the Oval Office, which is a symptom of an unhealthy work-life balance, among other things. When Tiffany Trump got engaged at the White House, her now-husband, Michael Boulous, did it in front of the White House Rose Garden. Obviously, that was not an option for Scavino given Trump’s recent renovations, but surely there is a spot on the property more picturesque than the path outside of his boss’s terribly decorated office.
Scavino and Elmore’s MAGA pals do not share my gripes. The comments on their shared Instagram post are filled with Trump allies sharing their well-wishes. Ivanka Trump and Tiffany Trump both shared how happy they were for the couple, as did Don Jr.’s girlfriend, Bettina Anderson. The comments section was a bit of a reunion for former White House press secretaries, with Sean Spicer, Sarah Huckabee Sanders, and Kayleigh McEnany all congratulating the pair.
Trump himself even shared his support. In a post on Truth Social, the president wrote, “What a great couple — Congratulations!” Maybe this means he’ll give them a good deal on the Mar-a-Lago ballroom.
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