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The Daily Dish Winter House

Brian Benni Shares an Update on His Dating Life and Reflects on His Breakup From Monica Shah

The Winter House-mate is on the quest for his "future wifey."

By Shannon Raphael

Brian Benni is still looking for his rom-com moment. 

How to Watch

Watch Winter House on Peacock and the Bravo app.

The self-described "hopeless romantic" is searching for more than just a ski trip fling on Winter House Season 3. Though he got swerved by Summer House: Martha's Vineyard cast member Jordan Emanuel on the Season 3 premiere, he's now setting his sights on newbie Casey Craig

On Episode 2 (which aired on October 31), Brian opened up about what his love life has been like, and he revealed more about his current relationship status — as well as his past breakup from Monica Shah — on the October 24 episode of Watch What Happens Live with Andy Cohen.

Brian Benni's Dating Life Today

As his Winter House bio notes, Brian is "ready to meet 'the one' and settle down." He wants to live "out his very own rom-com in a winter wonderland."

As soon as he arrived to Steamboat Springs, Colorado for the trip, Brian felt a connection with Jordan. However, after getting to know Casey, he recognized that the two had a lot in common. 

During a group dinner, Brian chatted with Kyle Cooke and Tom Schwartz about his love life. "I'm still feeling it out," Brian said about the ladies in the house, and Tom then asked if he was interested in Jordan at all. 

"Yeah, she's my type, but I can tell she's not into me," Brian added. "But Casey, she started talking, like, techie and nerdy to me, and she's smart as f-ck."

The following day, when the crew took a trip to the mountain to snowmobile, Brian further expressed interest in getting to know Casey better. "Casey, I haven't shown her any interest," he explained, and fellow cast member Kory Keefer advised him to let Casey do a little bit of chasing. 

"He's gonna crash and burn, for sure," Kory joked in a confessional on the episode. 

When he had a one-on-one chat with Casey after the snowmobiling excursion, Brian admitted that he was a hopeless romantic.

"That's all I am," he said to her. In an interview, Casey noted that she thinks of hopeless romantics as "wet noodle[s]."

Brian, however, wants to live out his romantic comedy fantasy. 

"I sort of sometimes think, like, 'Hey, maybe I could be Ryan Gosling. Maybe this could be my moment one day.' Who knows?" he said in his own confessional. I try to line up at least two dates, maybe three, a week. It's like Sales 101. You need to build a big pipeline and then, hopefully, one falls through that could be future wifey."

During his appearance on WWHL months after the trip ended, Brian revealed that Casey would have gotten his mom, Dharma Benni's, stamp of approval. 

"I would have to give it to Casey," he said about which lady his mom would have liked the best. "Definitely Casey, yeah."

Brian Benni sitting on the Watch What Happens stage as a guest.

Brian Benni Opens Up About His Breakup from Monica Shah

Though Brian is now on the lookout for his perfect match, viewers saw him in a relationship with Dr. Monica Shah on Season 2 of Family Karma. The pair broke up after the season concluded, and Brian opened up about what happened between the two when he appeared on WWHL

He said that he was the one who initiated the split, and that the two are in touch "for birthdays and events."

Brian then opened up about why they broke up. "I just think we were at different phases in life and maybe I wasn't ready for something very serious," he explained.

Find out what else Brian had to say about his romantic life by watching the video at the top of this post, and see him continue his quest for love on Winter House Season 3. New episodes air on Tuesdays at 9/8c on Bravo. Stream episodes the next day on Peacock

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