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“We were wasting time wallowing on the sidelines,” Stollak writes. Six weeks later, she was pregnant, and two years after that her husband admitted cheating on her.“We had to face the fact that neither of us were getting any younger or doing anything productive for our love lives.” Coming off a long-term relationship, Stollak wanted to get over her ex but also felt she needed “practice dating.” “What do you say on a first date? Then her hubby’s co-worker caught her eye across the table at a dinner.“I can’t believe you didn’t sock him in the face,” Granny offered.Gail wasn’t just giving advice — she wound up needing it from her granddaughter as well.“You just weren’t into him.” When it comes to dating, most twentysomethings want to leave their family — and their advice — out of it. Heartbroken over the end of a four-year relationship, the lower East Side resident, now 26, decided to jump into online dating — and managed to convince her granny to give it a try as well. He just wasn’t marriage material, Granny suggested.There was the man so shy he could barely speak, and a smug, self-professed “globetrotter” who had barely traveled and insulted her job at the time, being a cocktail waitress.
Online dating wasn’t easy for either of them — but over the past two years the pair did wind up finding love, at least in the relationship they developed with each other. “In the process of me trying to convince her, she said, ‘Okay, but you do it too,’” granny says.It sparked an affair that lasted the rest of her marriage, through her divorce in her early 40s and beyond.It’s a bond they forged night after night on the phone, recapping a blur of dinner-dates and cocktail meetups that Stollak details in her book “Granny Is My Wingman,” out Tuesday. “Kayli, I felt, should be going out,” says Gail, who agreed to this interview on the condition we withheld her last name to protect her status at a part-time job. “So I would do it on my level, she would do it on her level.Before they hit the Web, both Stollak and Gail were hung up on past loves. And we’d talk about it.” Stollak helped granny sign up for the Jewish dating website JDate, and Gail took to it like a pro, dialing down her age by two years and specifying she was only interested in finding a “worldly” man. She dated her ex-husband for only five weeks before tying the knot at 19 in 1954.
When Kayli Stollak got home from her first online date, she immediately called one of her best girlfriends and trusted confidante: her grandma Gail.
“You are definitely a girl who kisses on the first date,” her grandmother counseled. There was the diminutive “professional dater” who kept his phone crammed with numbers of girls he met on Ok Cupid.