Tracy Caliendo is mom to 12-year-old Hunter, 2-year-old Harlow, 20-month-old twins Piper and Presley and 11-month-old Dylan

By Hanna Flanagan
September 03, 2019 03:24 PM
Oku Okoko

After undergoing three rounds of in vitro fertilization and suffering one miscarriage, all Manhattan-based equity salesperson Tracy Caliendo wanted was a baby.

When she finally got pregnant from her fourth round of IVF in November 2016, Caliendo (already mom to now-12-year-old Hunter from a previous marriage) and husband Pete Pasetsky took one giant step of precaution: they hired a surrogate, who was implanted with two embryos.

“I kind of hedged my bet,” Caliendo, 43, tells PEOPLE. “I said, ‘Let me get a surrogate to carry two [embryos] so that hopefully one of us will end up having a child.’ “

“When I was working with the surrogate, she was like, ‘I don’t really want twins,’ ” adds Caliendo. “I said, ‘Oh, don’t worry. The chances of that are basically zero.’ “

But the odds were in her favor: Caliendo carried her baby to term and her surrogate gave birth to twins just five months later.

“When it rains, it pours,” she says, joking about welcoming daughter Harlow in August 2017 and twins Piper and Presley in January 2018. “We couldn’t even believe it.”

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Pete Pasetsky and Tracy Caliendo with their children
Oku Okoko

With three babies — whom the New York mom describes as “essentially triplets” — Caliendo and Pasetsky, a 42-year-old equity trader, were “beyond thrilled and over the moon.” At last, the couple had the big family they always dreamed of — and, much to their surprise, it was about to get even bigger.

Shortly after welcoming Piper and Presley, the parents of four found out they were expecting again.

“Out of nowhere, I ended up pregnant naturally, without even trying,” says Caliendo, who documents her journey on Instagram. “It was a bit frightening.”

Despite smooth pregnancies with Hunter and Harlow, her third was high-risk for both the mother and baby. Caliendo developed a serious condition called placenta accreta, which happens when the placenta grows too deeply into the uterine wall, according to the Mayo Clinic.

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“We found experts in the field. We had doctors who were wonderful, and I was very heavily watched,” says Caliendo. “I had to be seen by a doctor every two weeks from the day I found out I was pregnant and then once every week as I got closer to my due date. I wasn’t even allowed to leave New York City.”

On Sept. 21, 2018, Caliendo gave birth to Dylan at 29 weeks gestation. Though he has growth and fine motor skills hurdles to overcome, she says her kids are happy and healthy, and that she and her husband could not be more thankful for their unusual circumstances.

While raising their children — Hunter, 12, Harlow, 2, twins Piper and Presley, 20 months, and Dylan, 11 months — both parents are also now back to work.

“When you have to feed five kids, you know you’re going to be working the rest of your life,” Caliendo says, adding that she and her husband run a tight ship and have a full-time babysitter in order to stay sane.

Wake-up time is 6 a.m., followed by playtime at 7, milk at 9, lunch at noon, naptime at 1 and dinner at 5.

“We literally live by a clock,” says Caliendo. “But no matter how difficult the day gets, we always remember what it took to get here.”

“When you struggle, you do get a totally different perspective,” she adds. “When people say to me, ‘Oh my God, my kids are driving me crazy, I need a break,’ all I think to myself is, ‘You have these healthy children. You’re so lucky.’ “

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