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.

A few weeks ago I had dinner with a bunch of my friends. My ex-fiancé’s best friend, whom I hadn’t seen since September, was there. We had spoken on the phone maybe once or twice, exchanged a text or two, but otherwise it’d been radio silence for nearly a year.

This is a guy who, for more than 10 years, had seen me through breakups and make-ups, births and deaths, getting hired and laid off, and everything in between. In fact, I really should drop the ‘ex’s best friend’ title; he’s so much more than that. He’s the husband of one of my good friends, he was my date on my first sorority party, and even though we don’t speak often, he’s still one of my oldest friends. We have the sort of relationship where we can always pick up right where we left off. Before dinner that night, the last time I’d seen him was less than a week after my breakup, so we were both happy to hang out on better terms.

Catching up with him, I started thinking about friends, and the role they play in dating. It can be complicated, to say the least. As I’ve gotten older, the intricacies of some friendships have grown more and more, let’s say, interesting. I love all my friends. They’re smart, successful, fun, good people who care about my well-being, and vice versa. Meeting them can tell you a lot about me, but not right away. Before introducing a new date to your friends, you have to ask yourself: Are my friends benefits?

CALL ME "JACKIE" ONE MORE TIME...

Of course every situation is different, but one thing doesn’t change: I want to meet your friends. I want to see if they’re fun, if they’re good people, or if they’re complete degenerates. I want to see if we get along and vibe with each other, because if we don’t, you and I might not hang out anymore.

Your friends are important to me; I want you to like mine, and for me to like yours. I once dated a guy I knew from college, and he invited my girls and me to a sports bar to watch a Jets playoff game. I knew some of his boys from school, and my older brother went there too, so there was plenty of common ground. Problem was, the bar was packed, and there was a big group of them, so it was very overwhelming. (Read: not a good situation for a girl you just started dating.) Meeting some of his friends went something like: "This is Jamie" – "Who?" – "Jamie" - "What?" - "Jamie" - "Oh, Jackie!"

We squeezed by people, screamed in each other’s ears, and as sometimes happens, drank entirely too much in order to make the situation bearable. There was a lot said that night, but since I’ve already showcased some of my infamous TUI’s, there’s no need to embarrass myself again. That night was the beginning of the end of our relationship (if you can even call it that).

CHAIRS + DRINKS = SUCCESS (HOW HARD IS THAT?)

Meeting the entire posse at once isn’t always a bad thing, though. Take this other guy I dated for example. Just a few Saturday nights ago he told my friends and me to come meet him and some friends at a restaurant nearby. They were finishing dinner, and he asked that I please let him know how many girls I was with so that he could pull up the necessary number of chairs. I was hesitant. Would we be sitting on top of them? How crowded would it be? Would it be weird?

Luckily the answer was no. This guy knew what he was doing and played the situation perfectly. He pulled up two chairs, had his boys slide around so that I’d be next to him, and put my girl on the other side of me. His next move was even better. He called the waiter over to get us drinks. (Bonus tip: In every situation, getting your date a drink should be the first move.)

With the restaurant quiet, and with plenty of room at the table, the six of us actually got to know each other. He had told his boys just enough about me to make it comfortable. Whether he told them after the last time he and I hung out, or in the 30 seconds before my girls and I walked into the restaurant, I’ll never know. And it really isn’t important. On the flipside, my girl knew every gory date detail, but she played it like she barely knew a thing. That Jessica is very savvy—a friend who knows how to work to my dating benefit.

ONE-ON-ONE; OR, THE HALL & OATES APPROACH 

Group intros are fun and sometimes unavoidable, but there’s something to be said for the one-on-one meeting. I had late dinner reservations with this one guy on a Friday night, so he invited me to a bar in my neighborhood (bonus points) to watch some college hoops with him and his best friend first. He always talked about this guy, so I was excited to finally meet him.

The situation was perfect: the bar was quiet, he had a stool waiting for me next to him, and the game was on, so if all else failed, we could still talk about that. I already knew we’d be okay though; the best friend was a Cowboys fan. Regular readers know I’m an Eagles girl, so I wasn’t exactly worried about a lull in the conversation. As expected, there wasn’t, and we got along beautifully. Guys take note: This is how you introduce a woman to your best friend. A one-on-one gives us a chance to get a good read on each other in a comfortable setting.

HEY GENIUS! MAKE SURE YOUR FRIENDS DON’T HIT ON ME

My friends know me well. There are not many secrets—if any at all—that I keep from them. They know who I go out with, where they take me, what they drank, ate, wore, and said. If you meet my friends, that means I like you, though you won’t get much more out of them. It’s code—they’re my friends and friends keep each other’s stories to themselves.

I was out with this guy one night, having drinks at the bar before our table was ready, and we ran into a couple who were close friends of his. They sat down with us and started talking. What followed was hilarious and perfect for me, albeit somewhat embarrassing for him. They told me about his ex-girlfriend, what he did on their trip to Mexico, his obsession with working out, how he’s never on time…I could go on and on (as they did). You get the point.

Keep your people in check. Likewise for the friend that gets too friendly. I was out with this one guy when his friend stopped by to say hi (don’t ask, he was in the neighborhood?). Then he’s suddenly telling me that the girls who date his friend always end up sleeping with him. Really? Check, please. I won’t be going home with either of you idiots.

LESSON LEARNED

There is no hard and fast rule for when it’s appropriate to meet the friends. In each relationship, that amount of time will be different. I can tell you this much: I’ve met guys’ friends, dogs, cousins, trainers, neighbors, you name it. Once you introduce a woman to these folks, there’s no going back. So just think before you take this step, because she’s only going to feel like a greater part of your life afterward. Whatever the case may be, always make sure that your friends are benefits.

Next week: Jamie’s shares how to end it gracefully.

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