Love Is Blind’s Leo Gifts a Rolex to Jill Zarin’s Daughter Ally

In between art dealer Leo Braudy’s professional commitments at Art Basel Miami Beach, he met up with fellow reality TV star Jill Zarin’s daughter, Ally Shapiro, poking fun at their respective love life struggles.

“Too soon?” Ally, 31, captioned a Wednesday, December 4, TikTok video that she filmed with her mother, 61, and Leo, 31.

In the clip, Leo and Jill lip-synched the viral “I Love Your Daughter” dialogue sound, which is originally from Gilmore Girls.

“I love your daughter,” Leo said, pretending to beg the Real Housewives of New York City alum, who replied, “But, what do you have to offer her?”

Leo added that he had “nothing” except his art connections. The remaining footage spliced together moments of Leo and Ally taking in the exhibits and sipping white wine. In the end, he planted a kiss on his now-infamous Rolex watch and handed it over. Ally then fastened the bracelet on her wrist with a smile before walking away.

Leo appeared on season 7 of Love Is Blind, which was filmed in Washington D.C. in October 2023 and aired on Netflix earlier this fall. In the pods, Leo was involved in a love triangle with Hannah Jiles and eventual fiancée Brittany Wisniewski. He also raised eyebrows when he revealed that he brought a gilded Rolex watch into the experiment.

@allyshaps

Too soon? @leo_braudy #artbasel

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“It’s my fourth nicest watch, but it’s definitely my most sentimental because it’s a family heirloom,” Leo said in an October social media video. “The family story behind it — I think is pretty remarkable. A lot of the ‘Rolex talk’ in the pods was me and the guys talking about our families because a lot of us brought objects of significance with us.”

The watch was originally owned by Leo’s great-grandfather and was gifted by his children. (Leo’s grandparents and parents are deceased with the reality TV star inheriting their art dealership.)

“He loved it,” Leo added at the time. “He would actually wear this watch with [his] hammer. I got this hammer for my bar mitzvah [when I was 13] and it’s the only other thing I have from him. All the paintings that I hang for myself in my home, I do it with my great-grandfather’s hammer.”

He left the Love Is Blind pods engaged to Brittany, 33, but they split several days later and were not featured in the remaining episodes.

Ally, meanwhile, is newly single after calling off her whirlwind engagement with ex Jordan Bilfeld.

“I think there was a lot of love there,” Ally said on Jeff Lewis Live last month. “It was a three-year relationship, and it was my first serious relationship and, you know, I’m sure I’ll see him again and I wish him nothing but the best.”