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The Daily Dish Million Dollar Listing Los Angeles

Josh Flagg Shares a Look at Date Night with His Boyfriend *and* His Parents (PHOTO)

The Million Dollar Listing Los Angeles agent had a night out in paradise with his boyfriend and his parents.

By Casey Suglia

Josh Flagg is "still" living his best life in "paradise" with his boyfriend, Kelton Hovland. The Million Dollar Listing Los Angeles real estate agent has been on vacation in Hawaii over the past few weeks with his parents, his friends, and his boyfriend — and he still sharing looks into this super luxe life while out of office.

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Josh took to his Instagram Story over the weekend where he gave a brief look at a night inside of his tropical vacation. In the photo, Josh can be seen looking sunburnt and fabulous, wearing a burnt orange polo and hat, with his arm around Kelton who looks so relaxed as well. The couple was joined by Josh's parents, Michael and Cindy Flagg, who donned their finest resort wear to sit around the dinner table, which was filled with (almost) empty plates and full glasses of wine.

"Aloha...still," Josh wrote in the caption of the post, revealing that they are still on vacation on the island of Maui in Hawaii. 

Josh Flagg smiling with Kelton Hovland and family in Hawaii.

Inside Josh Flagg's tropical vacation in "paradise" with boyfriend, Kelton

Josh and Kelton have been on this super lovely and relaxing vacation since December — but they haven't had the best weather for some of the trip. Josh took to his Instagram Story on Dec. 28 where he posted a photo while he was out relaxing by the pool, with wind blowing in the air and clouds in the sky. 

"Well, this is paradise," Josh sarcastically captioned the photo.

Josh Flagg's Maui vacation.

But, things got much better in the evening, when Josh, Kelton, and their friends were able to gather together on the patio at the resort to play cards and indulge in some light bites and drinks. 

Josh Flagg's Maui vacation.

Details on Josh Flagg's Major Business Deal in NYC

Amid his tropical getaway, 2025 has been off to a great start for Josh. On Jan. 3, Josh took to Instagram where he announced that he made a major real estate acquisition with his family in Manhattan. 

The Real Deal first reported that Josh brokered the deal for a building on SoHo's Mercer Street, which is a prime destination for shopping. Flagg Family Capital, owned by Josh's parents, purchased the building for an undisclosed sum. "We are changing things up from our previous business model," Josh told the publication in a statement. "I am focusing on prime locations: Palm Beach, Miami, downtown New York...instead of shopping centers and office buildings, which is what we have traditionally done."

Who is Josh Flagg's boyfriend, Kelton Hovland?

Josh has been dating his boyfriend, Kelton Hovland, since early 2024 — but since Kelton is "a little more private," he hasn't shared much about him. Before hard launching the relationship on Instagram in September, Josh chatted with The Daily Dish in July, where he revealed that he's been spending more time in New York because of Kelton. 

"I'm in a serious relationship [with a] really good, nice guy who's from New York and lives in LA," Josh said. "So, we go back and forth together between New York and Los Angeles."

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