By Tessa Hayley Hellberg

Are there red flags in Jesse and Emma Watters’ age-gap marriage? My interview with Nicki Swift highlights the upside of age differences and how it can offer benefits to both partners.

Journalist Tessa Hayley Hellberg writes, “We’ve said in the past that Jesse Watters’ wife should run for the hills, but his hypocritical marriage rant isn’t the only reason why. While New York City relationship expert and creator of the “Love À La Carte Method” Susan Winter exclusively told us that this relationship isn’t necessarily doomed (more on that later!), the fact that his relationship with Emma DiGiovine started as an affair, to him constantly bringing her up while making controversial points, the red flags in this union are undeniable.”

A good number of people focus on the age difference and try to make that the issue. Honestly, there is a lot going on in this relationship, and the least of anyone’s concerns would be age. Jesse and Emma got off to a bit of a rocky start; Jesse was already married and Emma was a coworker when their relationship began.

One of the most unsettling red flags in their relationship is how it started. In 2022, Watters revealed on “The Five” that he deliberately let the air out of DiGiovine’s tires so she’d need a ride—and he never told her. He laughed it off, saying it was fine because they ended up married.

Red flags aside, one expert believes the couple may make it

Hellberg continues, “As we said earlier, relationship expert Susan Winter exclusively pointed out to Nicki Swift that there was hope yet.

For starters, their age gap. According to Winter, Watters being a whopping 14 years older than Emma DiGiovine wasn’t necessarily cause for concern — though she did call it “a cliché.” Winter explained, “The historical premium placed on a woman’s youth and beauty becomes a seductive choice in second marriages.” Again, Winter reiterated that it wasn’t a major hurdle, necessarily. “It’s an age old barter system — youth and beauty for power and success,” she said.

As such, she continued, there was actually a good chance Watters and DiGiovine may end up going the distance, with Winter noting, “These relationships tend to last as both individuals have valuable pieces to add to the collective whole.” As for another red flag, the fact that Watters and DiGiovine met at work (just as, ahem, Watters met his first wife on the job), Winter didn’t find fault with that either. “If someone meets both their first and second wife on the job, it only indicates they work an awful lot of hours,” Winter told us, pointing out that people often found love at work because that was where they spent most of their time.”

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