My granny is my wingman

Kayli Stollak, 24, buddied with her grandmother when diving into online dating waters.

Story highlights

  • Today's singles scene is diverse enough to include young professionals and granparents
  • Don't be afraid to try a different dating site if you're not getting the results you desire
  • Granny Gail: "Sex is now part of the program"
Finding a partner in crime when it comes to navigating your love life can be challenging.
Girlfriends tend to be over-supportive ("I think he's really into you -- it's only been a month since your last date. Give him time to call."). Mom and dad can be overprotective and judgmental ("Independent consultant is a fancy way to say unemployed."). And then...there's grandma -- a wealth of knowledge and experience, and someone who's already landed a man once.
Which is exactly why Kayli Stollak, 24, turned to her Granny Gail, 75, when she decided to jump into the online dating scene in New York City -- especially since Granny (who lives over 1500 miles away in South Florida) is playing the digital dating game herself.
As Stollak says, "She's a 24-hour cocktail party full of jokes, gossip, and advice." To record their triumphs (and low points), which they discuss almost daily over the phone, Stollak started a blog "Granny Is My Wingman."
Kayli and Granny share what they've learned since they logged on:
The profile mistake to avoid: Don't skimp on the details. "In most cases less is more," says Granny. "But when it comes to online dating that's not necessarily true." As Stollak explains: "Initially, we didn't share enough information about ourselves or the qualities we're looking for in future partners. We thought we were coming across as mysterious, but I think men probably saw us as vague or boring."
If it's not working, don't give up -- switch sites: Just as in the real world, some locations are better for meeting potential partners than others. Granny recently left for "The pool of men is much smaller for people of my age and Match has more guys in my area," she says, "As soon as I signed on, I attracted more messages and online winks."
Project the right image: Stollak's sister -- an OKCupid success story -- told her that people who have pictures of their faces rather than full-body shots get more clicks, so Granny and granddaughter both opt for headshots on their profile pages.
How the dating rules have changed: "I'm learning that men expect a woman to be more forward," Granny says, which includes calling him. "You have to be more aggressive, show more chutzpah," she adds. Another observation she's made -- especially within her granddaughter's generation -- is that sex is now part of the program. "I'm not promoting promiscuity," she says, "But if the sex is bad, why go further?"
One thing they'll never discuss: Nitty, gritty bedroom details. "That would be weird," says Stollak.
The ultimate deal-breaker: For Stollak: "A topless photo [of a potential suitor] taken in a mirror while flexing and sporting a kissy-face. I come across them way more than you'd think."
For Granny, it's a show-off, "He is dead wrong if he thinks I care about the kitschy list of homes he owns," she says. But a cheap man doesn't do it for her either: "A few months ago I was set up with an old fart who didn't want to pick me up because of the price of gas. Then he wanted to meet me at a quarter to six so we could make the early bird special," Granny says, "When I ordered a second glass of wine he looked at me and asked, 'Are you sure?' I was positive."
The #1 thing Kayli has learned from Granny: "She taught me to be more relaxed and open to new encounters," says Stollak, "She's always preaching that I'm young and need to take advantage of this time in my life and the options that are out there."
The #1 thing Granny has learned from Kayli: "She's always keeping a positive attitude -- I try to adopt her approach," Granny says, "If it's not fun, don't do it again, but find the humor in [the date] so we can laugh about it after."
Where they are now: Neither granny nor granddaughter have met their match. "Some guys come off hilarious, attractive, and intelligent online, but then you meet them and they're total duds that are clearly masters of deception and Photoshop," says Stollak. But until they both find "The One," married readers can still live vicariously through their stories (and voicemails) and those still dating can know that they're not alone.