Kelly Bensimon enjoys PDA-filled date with Connecticut businessman one year after abruptly calling off wedding

Kelly Bensimon enjoyed a PDA-filled date night with a Connecticut businessman in NYC this week on Wednesday. 

The RHONY alum, 57 – who recently spent quality time with one of her daughters – seemingly indulged in a belated birthday dinner with a man revealed to be financier Robert Flood.

The reality star’s outing comes nearly one year after she called off her wedding to Scott Litner just days before the official ceremony in June 2024. 

She arrived to a restaurant called Beefbar in the Tribeca area of the bustling city, and just minutes later she was joined by Flood who sported a navy suit jacket as well as denim jeans. 

The pair met outside of the eatery and exchanged a hug and a kiss before making their way inside. 

Kelly and Robert dined for around three hours and at one point, a small cake with a candle on top was delivered to their table. Earlier this month on May 1, Bensimon notably rang in her 57th birthday. 

Kelly Bensimon, 57, enjoyed a PDA-filled date night with a Connecticut businessman in NYC this week on Wednesday

The RHONY alum seemingly indulged in a belated birthday dinner with a man revealed to be financier Robert Flood

Afterwards, the two exited the restaurant and briefly stood outside while awaiting for an Uber to pick them up. 

Flood was seen laying a gentle kiss on her cheek as she lightly placed her hand on his back.

The TV personality flashed a peace sign in a friendly gesture towards fans before hopping inside a vehicle to head to her next destination with Robert. 

A source told Page Six that the Managing Director of Truist Securities has previously dated Tiger Woods’ former mistress and also podcast host Rachel Uchitel. 

However, whether Kelly has sparked up a romance with Flood or if the pair are simply pals is not known.  

Bensimon turned heads in a stylish look that comprised of a shimmering, dark blue miniskirt and matching blazer. 

She additionally opted for a black New York Yankees shirt and slipped into a pair of open-toed, silver strappy heels. 

Kelly’s long locks were parted in the middle, and effortlessly flowed down past her shoulders in elegant waves.  

She arrived to a restaurant called Beefbar in the Tribeca area of the bustling city, and just minutes later she was joined by Flood who sported a navy suit jacket as well as denim jeans

The pair met outside of the eatery and exchanged a hug and a kiss before making their way inside

Kelly and Robert dined for around three hours and at one point, a small cake with a candle on top was delivered to their table. Earlier this month on May 1, Bensimon notably rang in her 57th birthday

Afterwards, the two exited the restaurant and briefly stood outside while awaiting for an Uber to pick them up

Flood was seen laying a gentle kiss on her cheek as she lightly placed her hand on his back

The TV personality flashed a peace sign in a friendly gesture towards fans before hopping inside a vehicle to head to her next destination with Robert

The star’s latest outing this week comes almost one year after she called off her wedding to Scott Litner only days before the ceremony was set to take place. 

The former couple had gotten engaged in the summer of 2023 – but Kelly chose to not walk down the aisle when Litner refused to sign a prenup. 

In a statement to Page Six at the time, she expressed: ‘I have decided that my two daughters are my priority and I won’t be moving forward with this wedding.’ 

Kelly is mom to children Sea, 27, and Teddy, 24 – whom she shares with ex-husband Gilles Bensimon. The pair were married from 1997 until their split in 2006.  

Bensimon had also told People, ‘Ultimately, my decision is nobody’s business, but I understand that there is speculation and gossip, and I want to put an end to all of it.

‘To be clear, he refused to sign a prenuptial agreement, and I refused to marry him. Full stop.’

An accompanying statement also read: ‘She was looking forward to an exciting new chapter in her life together with Scott when everything became clear to her late on Tuesday afternoon.

‘[He] refused to sign a prenuptial agreement, effectively stalling their engagement mere days before the wedding.’

However, whether Kelly has sparked up a romance with Flood or if the pair are simply pals is not known

She additionally opted for a black New York Yankees shirt and slipped into a pair of open-toed, silver strappy heels

‘To be clear, he refused to sign a prenuptial agreement, and I refused to marry him. Full stop,’ Kelly said of Litner; former couple seen in 2023 in NYC 

Bensimon further explained, ‘He thought that I would enter this union without legal protections in place, that I would leave everything to faith. 

‘But I’ve worked really, really, hard as a single mother and have always made smart decisions for myself and my family, and that will continue.’ 

The following month in July, Kelly also informed DailyMail.com, ‘I’m obviously extremely disappointed, but it’s not something that just happened. This is something that was building up over time and the prenup was a big deal for me.

‘It’s like when you’re a single parent, whether you have thousands in your account or you have a 100 million in your account, women are going to need to protect themselves, and I’m just not going to take a risk.’ 

She also talked about how her circumstance has ‘opened a lot of doors’ when it comes to having conversations about prenuptial agreements. 

‘It’s about having personal respect and value, which I have. I’m raising two girls, who are really important to me. 

‘But the prenup is really important because it talks about more than just your own personal value,’ Bensimon added. 

‘I guess the biggest takeaway from this is just about protecting myself and my friends and being a solid female that people can come to.’

Kelly is mom to children Sea, 27, and Teddy, 24 – whom she shares with ex-husband Gilles Bensimon. The pair were married from 1997 until their split in 2006; seen with her daughters in 2024 in Jamaica 

‘I guess the biggest takeaway from this is just about protecting myself and my friends and being a solid female that people can come to,’ she told DailyMail.com; seen trying on wedding dresses in NYC in May 2024 

Kelly expressed, ‘I’ve had so many people reach out to me and say, This happened to me…I just have so much empathy for them, and I try to be a solid sounding board for them…’ 

Only two months after not going through with the wedding, the media personality had revealed to Page Six that she was stepping back into the dating scene.

‘I’m not in a relationship. I am…happy to move forward with new possibilities… [I’m] having fun dating.’ 

The Real Housewives alum continued, ‘I am enjoying myself. I am not hunting. I can’t wait for my next chapter. I am not in a committed relationship.’