Flirting Tips from My Grandma

Love advice from the hottest grandma on the block!


My grandmother has been married four times, often to younger men, and was known throughout my mother’s childhood, and much to the chagrin of my uncles, as the hottest mother on the block. Retiring from men in her 50s, she now quips that men are only good for two things: breeding and heavy lifting.

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Despite her cavalier attitude toward the less fair sex, she still bets me that if we went to a club together, she would walk home with more numbers. Sadly, I have to agree. My grandmother is willing to go up to anyone and start flirting – hot men in Beverly Hills, the women who sell us knock-off handbags in Chinatown, the checkout boy at Wal-Mart. She is filled with compliments, and loving pats on the shoulder, which often fall on the intended victim’s chest. When I am faced with a prospective suitor, my first response is to freeze, so I have no doubt that if we got into a pick-up competition, she would easily come out on top. Plus, as I explain to her, she has age on her side, like Betty White, people find her novel, charming, like a Christmas ornament.

Though Nana, as she is known worldwide, is approaching octogenarian status, she looks far younger than the frosty-highlighted, pant-suited Ms. White. My grandmother wears Michael Stars knits and Prada heels. She loves Marc Jacobs, though she thinks some of his clothes are little dowdy. She can’t stand anything that smacks of vintage, complaining that she’s already worn that outfit in the 50s, 60, 70s, why would she want to wear it again? She hates old people and anything that’s not on sale. And she loves to flirt.

“It’s not that hard, Kristen,” she snorts at me over Skype, videoconferencing having revolutionized her social life. “But then again, I’m like Charlie Sheen, I’ve got tigress blood.”

So I figure that I’ll take her up on her bravado, asking, “Alright then, Nana, what are your flirting secrets?” And this is what she said – the ABCs of picking up men:

1. Always Be Confident – “The problem with women these days,” Nana shares, “is that they are too desperate. They are willing to put out, but they won’t just go up to a guy and start talking to him, they want the guy to come to them. When I would go to clubs, I would say, ‘Here I come, you lucky bastards,’ because Miss Cool was walking into the club. Walk up and act like you’re a buddy, you’re just part of the group. Don’t treat them like a stranger, treat them like Wendy Williams does, say, ‘How ya doing?’”

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But Nana’s advice doesn’t end there (this is why I’m still in therapy): “You should always have tan legs because milk white legs are not appealing. I sound like Joan Rivers but that’s true. Better your legs be tan than your face, honest to God! That’s my theory. And bright pink toenail polish, that’s another one. People notice, that’s why when I go to Los Angeles, everyone says, ‘Oh I love your toenail polish, even though they’re gay.’”

2. Always Be Complimenting – Nana explains that nothing breaks the ice like a compliment, “Tell them, ‘Gee, you’re so cute,’ or ‘Oh, I love your hair.’ Guys like it when you like their hair. Also, ‘Boy, you’re buff, do you work out a lot?’ or ‘If I were only fifty years younger, you’d be my type.’ I say that one a lot.”

I try to explain that this last one really doesn’t work for my demographic, but Nana disagrees, “Why not? It will make them laugh.” She explains that the compliment is just the conversation starter. I ask Nana if that’s what she did to pick up her husbands. She snickers, “Oh, they picked me up. With my first husband, he had a garage and I worked in the record store and I used to walk by there real sexy. I was 12. I’m sure I complimented him too. I always loved men, even then.” Ah, Nana Lolita, knocking them dead since pre-pubescence. No wonder I am so far behind her game, at 12, I could barely say hello to boys my age, let alone the local mechanic.

3. Always Be Curious – “You have to ask questions,” Nana advises. “Did I tell you what happened with the electric company?” I am not sure what this has to do with picking up men, but I go along with it. Nana is pleased I haven’t heard this one, “Well, my electric bill is so high that I usually only pay half of it, but this time, I got a disconnection notice, and so I got a guy on the phone and he said I wouldn’t be disconnected. I told him that I wasn’t sure I could trust him so I would need his name, his address, his phone number, I was just being funny, you know. And he told me his name was Vince Edwards. Do you remember Vince Edwards from Dr. Casey?”

Again, I don’t what this has to do with picking up men, and I have no clue who she is talking about. She explains, “Dr. Casey was this real old TV show, it was one of the first medical dramas. Anyway, I ask the guy if he was named after the show, and he gets real excited because I guess he was, his mother loved the show, but nobody remembers it. So I asked him where he lives, and he told me Panama. Panama!! Why is my electric company in Panama? I couldn’t believe it. So you see, you should always ask questions, especially if they are in a call center. Because of my electric bill being disconnected, I got to talk to Vince Edwards in Panama!”

My grandmother says that I can use her age in this article, but that I need to clarify that she is not like most 78-year-olds. “Don’t worry, Nana, I think the fact that you compared yourself to Charlie Sheen will take care of that.”

What I don’t say is that I just learned more about flirting in our ten-minute call then I knew my whole life. Because being confident, offering compliments, and asking questions are all you need to approach the cute guy standing across the room, looking around like he would rather be anywhere else, but secretly wishing that some girl would come up to him, tell him she loves his hair, and ask him his name and where he’s from. We are all Miss Cool, and it’s about time, we let it out, declaring, “Here we come, you lucky bastards,” and meeting some men in the process.

I still don’t think I would ever refer to anyone as buff, but maybe now, I’ll at least give Nana a run for her money.

Kristen McGuiness is the author of 51/50: The Magical Adventures of a Single Life.

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