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Dating Dilemmas? Dial-A-Granny!

Your fairy grandmother is on the line...

When it comes to chatting up a QT at the bar, we all know three is never a crowd— having your girlfriend within arms reach is always a good idea. She’s there as an ice-breaker, an exit plan, and if the vibe is right, she’s also really good at disappearing. NY-based writer Kayli Stollak knows a thing or two about wingmen, she wrote a damn book about it! But here’s the rub, her grandmother is her wingman! So, what does a mature woman know about dating in a world littered with twerking, selfies, and sexting? Well, it turns out a lot. When it comes to dating, it seems as though some things have changed but many things are still the same. Kayli Skypes her granny below.

Kayli Stollak: OK, Granny. Let’s start with the important stuff. Who’s cuter, Justin Bieber or Robert Pattinson?
Granny StollakHonestly, I’m not crazy about either one of them. Justin Bieber is a silly kid and Pattinson I don’t know much about nor do I care to.

Who would you rather party with, Miley or Ke$ha?
Definitely not Miley Cyrus, I think she needs to do some serious growing up, she’s getting older, it’s time for her to mature a little and put some clothes on.

Rihanna or Katy Perry?
Oh dear, you’re picking real winners here. I’d go with Rihanna. Katy Perry is talented but a very silly girl.

Onto to dating, who pays on the first date?
Whoever asks the person out in the first place! Truthfully, I think the guy pays, but the rules have changed. If a girl says to him, “Let’s grab some coffee,” she should pay. But if he offers, as a gentleman does, you say “Thank you, that’s lovely. I’ll have a cappuccino.”

Is it appropriate for a girl to ask a guy out?
In today’s world, yes. But only if he’s giving out some strong vibes that he’s interested in her, otherwise leave him alone. Move on. Next!

What are your thoughts on posting topless or bikini pics on your dating profile?
Absolutely not. It’s inappropriate. You’re sending a message that you’re here and ready and interested in sex. You’re going to get back what you put out. Even if a girl’s planning on sleeping with a man now or in three months, it’s still wrong. How about a little mystery? If you disagree go find yourself a nudist colony.

What advice would you give yourself at 26?
I’d say, “Boy, you have a lot of responsibility, you better act accordingly.” You have to remember when I was 26 years-old I had a six year-old child and I had already started an affair. I didn’t do what I should have. You’re asking a pointed question, I’m giving an honest answer.

What’s the biggest difference about NYC from your teenage years to today?
Well there’s certainly way more people in New York today, it’s definitely more crowded. I think it’s better than it was. New York’s become more of a progressive city. People have learned how to get along better with people who are different from them, but they still have a ways to go.

What was the hot spot to go out with your girlfriends to when you were a young gal in the city?
We would go to a dance to meet guys, that was how you hooked up back then. That’s how I met your grandfather. I went to many dances at the McAlpin Hotel, it was near Broadway. Dances were always very crowded, with a band playing and people mingling and dancing. You’d stand with your girlfriends until some guy says dance with me, then you go. Unless of course you have no interest in dancing with him because you know immediately you have no interest in spending the evening with him. In that case you say, “Sorry, I’m tired right now. Blah blah blah.” You know, something to send him on his way.

If you could go on a date with one movie star, alive or dead, who would it be and why?
I’m not a movie star person, I consider myself more of a politician person. Bill Clinton is very smart, he’s a little young for me though. I like someone’s mind, how bright, how intelligent, how fast—that’s what attracts me. When a man speaks and he knows what he’s talking about, rather than rattling off a bunch of baloney, that’s what turns me on. I’m attracted to the mind, what people think and say and and feel and do, rather than how they look.

Today it’s the twerk, what was the talked about dance move when you were out on the scene?
The cha-cha! It could be very sexy, but it could also be not sexy. You know the cha-cha? It was 1-2-1-2-3. He’d go back, you’d go forward. He’d go forward, you’d go back. He’d go to the side you go to the side. The cha-cha was the hot big thing.

Who has more intimacy in their generations? Yours or mine?
Intimacy in my generation was kept very quiet, girls didn’t even share sex details with their other girlfriends in most cases. Which I guess actually makes the experience more intimate. It makes it more personal, it’s just between you and me, not you, my girlfriends, the Internet, and me. We weren’t telling our friends if we slept with someone the night before and exactly what we were doing in that encounter. Today the girls want everyone to know what they’re getting up to and I don’t think that’s such a good thing.

Are cell phones making our lives better or worse?
Cell phones can make our lives easier in many ways but you need to know how to handle them. It’s kind of sad when you’re out with your boyfriend and he’s on his cell phone and you’re on your cell phone and you’re both emailing and messaging everybody—but you’re not talking to each other! They take away from the conversations in the moment. People aren’t talking to each other as much and that’s what you should be doing.

Photography by Tricia VanGessel

E-mail me pippa@sousstyle.com!