Ryan Seacrest Reveals His Dating ‘Red Flags’ as He Sets Out To Find Love Again After Relisting His Very Romantic Napa Valley Estate

TV personality Ryan Seacrest has opened up about his dating red flags, while admitting that he may soon open himself up to apps like Tinder in his quest to find love, two years after ending a yearslong romance with model Aubrey Paige.

Addressing his dating struggles in the latest episode of his podcast, “On Air With Ryan Seacrest,” the 51-year-old gave a short list of “red flags” for any future love interests—noting that he is turned off by anyone who doesn’t greet another person while biking or running.

“When you’re out on a run or a walk or a bike ride, do you say hi to people that pass? If you don’t, I’m not so sure about you,” he joked. He added that he likes to take his dates out for a “little exercise” as a “test” to see how they interact with others.

As for his “green flags,” Seacrest called attention to another morning ritual, specifically his preferred beverage.

“I really look forward to getting up and having my coffee,” he explained. “I think if we can’t share that moment together, it’s a red flag. So, ‘I need coffee’ is a green flag. Don’t have a lot, and please don’t put milks and stuff in it.”

Ryan Seacrest appears to be embracing a season of change, recently revealing that he is open to trying out dating apps such as Tinder—mere weeks after listing the Napa Valley estate he has owned since 2020. (Realtor.com)
The 51-year-old previously described the St. Helena, CA, property as the place where he feels most able to unwind. (Realtor.com)
He initially listed the home in April 2025—exactly 12 months after he split from Aubrey Paige, whom he had dated for three years. (Realtor.com)

He later said that he planned to “be on Tinder” later that night so he could begin his search for the ideal partner. It’s unclear whether he’s had any luck.

Seacrest appears to be embracing a significant season of change in his personal life of late—having just relisted his sprawling Napa Valley estate for $19.8 million. This is the second time he has attempted to offload the picturesque property.

He initially listed the home in April 2025—exactly 12 months after he split from Paige, whom he had dated for three years. Before Paige, he dated chef Shayna Taylor from 2013 to 2020. He also previously had a relationship with dancer Julianne Hough.

Interestingly, his Napa Valley abode, which is located in St. Helena, CA, would likely serve as the ideal spot to have a date—with Seacrest previously revealing that it is the place where he feels most able to “slow down and take it all in.”

“It’s such a peaceful spot, and the views out over the valley floor are unforgettable,” he said in a press release announcing the listing. “You can even see the hot-air balloons drifting by in the distance. It’s the kind of place where you naturally want to slow down and take it all in.”

The home spans 10,750 square feet, which includes five bedrooms and six bathrooms.

The listing, which is held by Cyd Greer of Coldwell Banker Boker of the Valley, highlights the pool, guesthouse, cottage, and more amenities.

“Originally built in 2004, the property underwent a significant remodel in 2023/2024, blending timeless elegance with a fresh, light-filled space tailored for today’s modern lifestyle,” the listing reads. (Realtor.com)
The home features several enormous living spaces, including a chef’s kitchen with a fireplace. (Realtor.com)
The 10,750-square-foot home has five bedrooms and six bathrooms. (Realtor.com)
Throughout the home, enormous walls of windows create indoor-outdoor flow. (Realtor.com)
Luxe details include reclaimed wood beams and wide-plank oak floors. Custom cabinetry, lighting, doors, and windows were all installed. (Realtor.com)

“Originally built in 2004, the property underwent a significant remodel in 2023/2024, blending timeless elegance with a fresh, light-filled space tailored for today’s modern lifestyle,” the listing reads.

The luxurious property is surrounded by lush greenery, which adds another layer of privacy to the remote setting.

Upon entering the home, guests are greeted with an expansive living area with a soaring ceiling, a chic fireplace, and access to the outdoor area.

The dining area boasts an all-white color palette and a wood-beamed ceiling.

“Built to exceptional standards, the home showcases chiseled limestone walls, reclaimed wood beams, seven fireplaces, and expansive pocketing doors seamlessly connect indoor and outdoor living spaces. Outdoor living areas feature an infinity-edge pool and spa, a spacious central courtyard for large scale dining, inviting view terraces, a bocce court and a 220-tree Italian olive grove,” adds the listing.

Highlights of the main house include an inner courtyard, a chef’s kitchen, and a spacious primary suite with an office and private terrace.

The layout includes a library gallery, TV room, gym, laundry, garden room, storage room, and three-car garage.

“It’s such a peaceful spot, and the views out over the valley floor are unforgettable,” he said in a press release announcing the listing. (Realtor.com)
Outside, mature trees and native plantings dot the landscape, which also sports an infinity pool and spa and a bocce court. (Realtor.com)
There are multiple outdoor dining and entertaining spaces. (Realtor.com)
“Located just minutes from Meadowood Resort and downtown Saint Helena, this Napa Valley estate promises a lifestyle of luxury, privacy, and sophistication, perfectly suited for those seeking the ultimate in resort-style living,” adds the listing. (Realtor.com)

Luxe details include reclaimed wood beams and wide-plank oak floors. Custom cabinetry, lighting, doors, and windows were all installed.

There are seven wood-burning fireplaces in the main house, including a kitchen fireplace with a rotisserie and a pizza oven. The living room has a dry bar and pocket doors to the side terrace.

Outside, mature trees and native plantings dot the landscape, which also sports an infinity pool and spa and a bocce court.

Seacrest added 220 fruiting Italian olive trees. The property is equipped with security and surveillance systems, built-in audio, a Lutron lighting system, and a whole-property backup generator.

The luxe bathrooms boast marble vanities, soaking tubs, and glass-enclosed showers.

“Located just minutes from Meadowood Resort and downtown Saint Helena, this Napa Valley estate promises a lifestyle of luxury, privacy, and sophistication, perfectly suited for those seeking the ultimate in resort-style living,” adds the listing.

Seacrest previously attempted to offload the home in 2024 for $22 million. He took it off the market the following year.