Jamie Shupak is the Emmy-nominated traffic reporter for NY1, the Big Apple cable network that’s the end-all and be-all on all things Gotham for New Yorkers. She’s also a beautiful, single woman navigating New York’s treacherous (and hilarious!) dating scene. In her weekly column she shares her war stories and offers her advice and admonitions.

The response to my column has been overwhelming. There are my editors, simultaneously laughing and cringing at the sometimes ill-informed moves that guys make; my family, who week after week cheer me on through email and text; and my closest friends, who have made it a game to try and correctly identify which guy I was writing about in a particular column. All of this I more or less expected. But as a burgeoning columnist, I was most surprised by all the questions I've received from readers, most of whom are complete strangers. It makes me almost as happy as an Eagles playoff win, getting these emails and tweets from readers wanting answers to their dating dilemmas, intimate situations, and sometimes, just wanting to tell me about a funny thing that happened last Friday night. Being the traffic girl that wakes up viewers to tell them how long they'll have to wait on the George Washington Bridge that morning, I'm used to this kind of familiarity with strangers. And I'm more than happy to offer a hand.

Dear Jamie:
I’m a 34-year-old lawyer who is basically a walking version of Destiny’s Child's “Independent Women”—the shoes, the clothes, the house, the car, I bought it. I have been really lucky with dating in that things usually go well—I’m meeting great guys and having easy conversation over great dinners. Until the check comes. I never know what to do. I can clearly afford my share of the damage, but am I supposed to offer to pay? Shouldn’t he pay? I split the bill at dinner with my girlfriends, but come on, not when I’m on a date. Don’t you agree? What is a girl supposed to do when the bill comes?

Dear Splitsies No Waysies,
I agree that it can sometimes be a sticky situation, which is why I always appreciate a guy who stares the awkwardness in the face by just picking up the check and putting it by him. Not that I need or want him to pay, but it does eliminate the game of check roulette, allowing us to continue our conversation uninterrupted. While it's nice when the man pays (and according to many women I know what they should be doing), you should know better than anyone, Miss Independent, that it is no longer 1975. Offer to split it! Be polite and show your independence; it’ll make him respect you even more. Between you and me, ninety-nine percent of the guys I’ve been out with will laugh or say something like, "Don’t ever take your wallet out in front of me," or, "I’ll never let you pay," so chances are you won’t be grabbing for your Benjamins anyway. But be a lady and don’t ever assume or count on other people’s money. Let him tell you that he’s got it, as opposed to him thinking you’re some kind of gold digger, and everyone will be better off in the end.

Dear Jamie:
I need some advice. I’m an outgoing 30-year-old guy and someone gave me the number of a girl they want me to take out. Like I said, I’m not shy, but I have no idea what to say. What should the initial phone call be? “Hi, how are you, I got your number from XXX, are you free Thursday?” Do I have to chat with her for a while? I always struggle with this because I don’t want to come across as short or rude, but I also don’t want to sit on the phone and chit chat for an hour. Do you have any insight or advice?

Dear Tongue-Tied,
I've been on the receiving end of calls like this a lot lately. Here’s what I would do: Call and say what exactly you wrote me—"Hi, got your number from XXX"—then make a little small talk but don't feel like you need to sit and gab for a long time, after all, you’ve never met the girl. Like I wrote in my very first column about the intro email: see when she's free, flirt a little, make a plan, and then get off the phone. I've been in situations where we talk much more than I ever expected because we hit it off, but plenty of other times it's all business. Both are totally fine. You know what else, Tongue-Tied? You’re at an advantage being the caller as opposed to the callee. Have an excuse ready, something like, "I have to shower and go meet my boys for dinner," or, "I’m about to watch the series finale of Oprah" (you are, right?). Whatever it is, just have the line ready in your arsenal for when you need to say buh-bye.

Dear Jamie:
My single friend and I go to bars, clubs, lounges, etc., hoping to meet cute guys. But men do not approach us. We’re both in our early twenties, in great shape, work in fashion, have nice apartments, and are ready for some fun! But it’s like we’re wearing man-repellent! We watch guys approach girls far less attractive than we are and it’s so frustrating. What felony are we committing?

Miss Demeanor, my darling:
I don’t presume you're committing any real crime, but let’s take a little test just to make sure. Anytime you enter a new venue, ask yourself these three questions:

1. Are you standing with your arms folded, snarling at the crowd?
2. Are your hair and makeup so dolled out that you look like you just walked off the Broadway stage?
3. Have you already dismissed the probably hilarious and charming Zach Galifianakis type because he doesn’t meet your hyper-specific future boyfriend mold?

If you answer yes to any of the three, the only felony here is that you’re standing in your own way. What I've learned is that being approachable gets you far more numbers than being pretty. The vibe you give off determines what you’ll get in return. Smiling, making eye contact, saying hello, having a good time, and laughing with your friend will draw men in. They care less about your brand new Louboutins or Chanel bag, and much more about whether or not you look like you’re having fun. So stop being so judgmental, Miss Demeanor, and let loose a little. Order another Skinnygirl Margarita and enjoy yourself. The men will come.

Let’s also talk for a moment about meeting guys in a bar, club or lounge. While I applaud you for going out, it’s not always easy, I know; have you thought about trying another avenue? There’s a great barbershop next door to my best friend’s apartment that’s always swarming with good-looking guys (I’d tell you where, but they’re hers, proprietarily of course) but try to find a spot like that in your neighborhood. Better yet? Go hit a bucket of balls at the indoor driving range. Go to the next Yankees or Mets game. Go for a walk on the pier—it’s Fleet Week! Use your brains! Where do high-caliber men outnumber women eight to one? Go there. Just don’t forget to uncross your arms and smile.

Dear Jamie:
I’m 26 and I’ve been dating this woman who’s 34 for a few months now. We get along perfectly—both emotionally and physically—and we always have a blast when we’re together. Here’s the thing. I still have reservations about her age and always find myself asking both in my own head and to my friends: is she too old for me, is it weird to date a woman 8 years my senior? So far it hasn’t really been an issue, but I feel like it’s going to come up eventually as things progress. What should I do? How old is too old for a 26-year-old guy?

Dear Cougartown,
I firmly stand by the old adage that age is just a number. In fact, I dated a guy who was 9 years older than me and it was never an issue. When I first asked my Dad what he thought, he made a valid point about having more in common with someone who’s your peer, which I absolutely agree with—similar experiences, music taste, you name it—but when two people get along, why fight it?

However, age can only remain a moot point if both parties are mature and on the same page. So, Courgartown, if your 34-year-old lover is ready to wife up and start making babies then you have to ask yourself if you’re game for that. Likewise, if you’re still living the post-frat life with your homies multiple nights a week, she might not be cool with that either. Society can put a lot of unnecessary pressure on things like age difference, so it’s up to you to either conform or rally against it. I’m 29 and I’ve dated men who are 25, and men who are 38, neither of which you would have guessed based on looks alone. At the end of the day I really don’t care what year you were born, I only care what kind of person you are. As long as the 26-year-old you is cool with the 34-year-old her, and vice versa, then let the only number you worry about be her phone number when you call to tell her how beautiful—and young—she looks.

Next week: Jamie shares where you have the best chance of meeting a woman you’d actually like to date.

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