‘The Bachelor’: These Women Won’t Go Far With Matt James, According To Relationship Expert Rori Sassoon

Matt James‘ season of The Bachelor has officially begun. Bachelor Nation has their opinions about who James could end up with, but Showbiz Cheat Sheet got a professional opinion from matchmaker Rori Sassoon. We spoke with the relationship expert over the phone about the women she feels don’t stand a chance with James. 

Victoria Larson and Matt James
Victoria Larson and Matt James | Craig Sjodin via Getty Images

Rori Sasson is an expert with matchmaking and relationships

Sassoon has an extensive background in relationships and matchmaking. In the past, she worked closely with The Real Housewives of New York, using her expertise to create a speed-dating event for the Housewives and even giving relationship advice to Ramona Singer. 

When it comes to The Bachelor, Sassoon has a knack for choosing who is most likely to stay and who is most likely to go. That’s due to the skills used in Sassoon’s professional career.

“I put people together through a matchmaking service,” she explained. “We personality profile people, and it’s all about body language.” 

During our conversation, Sassoon gave her expert opinion on the women of James’ season — many of whom Sassoon thinks stood out negatively and won’t last long on the reality show.

Rori Sassoon wonders if ‘Queen Victoria’ Larson is ‘insane’ 

First up on our list of Bachelor contestants to talk about — Victoria Larson. She made one of the grandest entrances in Bachelor history, being carried in on a throne. 

“That girl Victoria,” Sassoon started. “I was like, ‘Is she insane? Is she insane?'”

Sassoon continued to be candid about Larson. “Not to be mean, like you’re not the prettiest girl there,” she said of Larson’s confidence. “And your attitude — your arrogance. There’s a very, very big difference [between] confidence and arrogance. [Larson] was clearly arrogant.” 

Sassoon wondered what made Larson feel she was “so terrific” she felt the need to “showcase that persona.” 

“People are very into [wanting] to be memorable,” Sassoon explained. But in Larson’s case, Sassoon says she was memorable in a negative way. 

Another thing that bothered the relationship expert about Larson was her inability to give the other women a chance. Sassoon pointed out the multiple women who didn’t talk to James on night one and wondered why Larson inserted herself into that narrative.

For now, it seems like James — or production — is into the villainy Larson has created.

Kit Keenan’s gimmicks won’t impress Matt James in the long run

During our conversation, we discussed many of the over-the-top entrances from the season 25 premiere of The Bachelor. Kit Keenan was another woman with “gimmick” planned for James. The fashion entrepreneur from New York arrived in a Bentley — something that irked Sassoon. 

“The girl Kit, I didn’t go for,” Sassoon said. “She was like, ‘I’m from New York!'” she added with a burst of New Yorker gusto. Sassoon says unlike Keenan, the women who were confident enough in their own skin arrived without “the gimmicks and the gadgets.”

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“If you are confident — truly confident in who you are, you don’t need to show up with some grand entrance,” she added. “You don’t need to be half-naked [referencing Kaili Anderson’s entrance]. You could show up comfortable, classy, [and] elegant. Be true to who you are.” 

Rori Sassoon says men like the chase, but Kaili Anderson didn’t give Matt James the chance 

Speaking of Anderson, Sassoon had plenty to say about her first impression on James. 

“I’m a big believer of ‘Why buy the cow when you can get the milk for free?'” Sassoon said of Anderson’s decision to wear lingerie while greeting James.

Even if you have the best body in the world, [add] a little mystery sweetheart. Understand you don’t have a second chance to make a first impression. Do you want him to really just like you for your body and for the outfit?

In Sassoon’s opinion, Anderson had minimal connection with James because of her choice to go cash in on appearances instead of having a conversation. 

Anna Redman screams ‘desperado’ on ‘The Bachelor’ 

When we asked Sassoon about Anna Redman’s intense feelings for James, she said Redman was “screaming desperado.”

“I don’t care who you are — a man likes a challenge a little bit,” Sassoon said, adding:

I’m not saying you have to be super hard to get. But [Redman] was just too desperate for me.

Most men I’ve ever spoken to [will] run the other way [when a woman is coming off as ‘Please, I’m desperate’] unless they’re insecure.

She doesn’t think Redman will last long on The Bachelor.

Rori Sassoon’s thinks Matt James could end up with Chelsea Vaughn or Abigail Heringer 

It’s still too early to tell, but Sassoon says a few stand-out women could be a good match for James. Among them is runway model Chelsea Vaughn and financial manager Abigail Heringer.

Sassoon feels both women carried themselves with “quiet confidence,” and James noticed. She won’t be surprised if the Bachelor chooses Heringer or Vaughn in the end.