Getting Around Town With Jamie Shupak: 5 Sure Ways to Land a Second Date

Getting Around Town With Jamie Shupak: 5 Sure Ways to Land a Second Date

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.

It was 8:34 a.m. back on December 6, and I thought I had hit the jackpot. Check out this direct message I got on Twitter from the account of a star of the Philadelphia Eagles:

jamie_dm

The “funny story” was that he saw me on TV, did some P.I. work to find out I was from Philly, and wanted to take me to the Eagles/Giants game on Sunday, December 19. Before we talk about the 5 sure ways to land a second date, let’s get something straight. If in fact you have season tickets to the Eagles, and a helicopter to get us back and forth from NYC to the games, no need for a second date with me…or third or fourth, for that matter. Have your people call my people; we’re going straight to the altar.

Well, not so fast…

1. PAY ATTENTION TO ME

All I had to do was go out with this agent guy one time before the game. Easy, right? So we meet for drinks at a bar in midtown, because “one of my other clients has this event later, and I have to drop something off to him there.” I’m easy-going, no problem. We ate, we drank, we talked, it was fine.

At this point I’m thinking, I am so going to this game. Then, we go to this event next door where his star client (this time, a New York Giant) is hawking some sports drink. The agent proceeds to leave me at a table with his client while he works the room, schmoozing every person there, for over an hour. I’m not a needy girl, but really? This was our first date and this dude is nowhere to be found. I’m sitting at a table with this Super Bowl star wide receiver, and for the record: Yes, we talked about leaving to get a drink together and ditching the agent, but I’m too nice.

Lucky for me I like football and can roll with any situation… but this was beyond. When he came back, he kept telling me how cool this was, how cool he was, and how cool his clients are. Problem was, none of it was actually cool. I love the Eagles as much as any other crazy Philadelphia fan, but trust me, no game was big enough to justify his arrogance and ignorance that night.

There did however wind up being a funny part to the story…that this game had one of the most exciting moments in sports history. My Eagles came back from a 21-point deficit that day, in the best 8 minutes, 9 seconds of football I’ve ever seen. Luckily for me I was with my brother and sister-in-law, and not this smarmy agent guy. Lesson learned: Eagles tickets might not buy you a second date after all, but being a gentleman is a good start.

2. DON'T COMPLAIN

...to the waiter, hostess or bartender. It’s so unattractive. If you’re giving them a hard time about the temperature of the restaurant, or the strength of your drink, I can’t imagine (nor do I want to) what it would be like to be your girlfriend. However you treat these people is how I’m pretty sure you’re going to treat me, so be nice.

Sounds elementary, but I have friends who have been out with guys who don’t say please and thank you to the waiter. Didn’t your Mom teach you anything? Good manners go a long way. So does being pleasant, no one likes a Negative Nancy. My house growing up was a strict "No Whining" zone. (There may have even been a sign saying so in the kitchen.)

Either way, I don’t want to hear you complain about your job, your living situation, or being single. Life’s too short to be miserable. If you don’t like something, change it. And if you can’t change it, call your Mom and tell her, she has to listen, I don’t.

3. "CAN I TAKE YOU HOME?"

By which I mean, make sure your date gets home safe—not "Can I come back to your place?" Come on people, my 93-year-old grandfather reads these columns; can we keep this PG please?

But really, making sure I get home safe is a sure way to land a second date. Bonus insider scoop: if you pick me up AND drop me off for a date, that will automatically land you dates 2-5, no questions asked. That is, unless my best friend digs up disturbing information on you on Facebook (which has happened, most of my friends do have unofficial side jobs as private investigators).

Anyway, back to the story: there was a guy who told me he was going to pick me up at 8 for our date one night, and I was floored. Pick me up? What does that even mean? This was going to be good. I barely paid attention to anything else that happened that night, 'cause it just didn’t matter. He had, as he called it, chivalrosity. Grammatically correct or not, I liked it. So did Helen and Neil (my parents) when they got word of this.

Make sure I get home safe, and you will look like a good dude, with good intentions. I’ll find out soon if you’re faking, but at least you’re going to get that second date.

4. ABC: ALWAYS BE CLOSING

There was an article in the New York Times this past weekend that said, “Phone calls are rude. Intrusive. Awkward.” I’m not here to debate that. But after even the best of dates, you have to close the deal.

What is the proper follow up? I’ll tell you: Call me. I went out with a guy on a Thursday night, had a great time, and Saturday morning my phone rings. Bonus for this guy, I was with my whole family when he called—and they were impressed. How could I possibly say no to another date when he was the first guy to make a (gasp!) voice-to-voice call and ask me out?

I was going to go out with him anyway, but I loved that he stared the awkwardness in the face and called me. It showed he was interested, confident, and had good manners. Check, check, check. A text or email is fine and does the trick most of the time, but a phone call will get you in for sure. So channel your inner Alec Baldwin in Glengarry Glen Ross and "A-B-C."

5. CHALLENGE ME TO SOMETHING...ANYTHING

The best dates I’ve been on are the ones where we do something. I’ve played ping pong for beers, for a third date, for cottage cheese (don’t ask), and for concert tickets. Have fun with it—don’t take yourself too seriously. But be a man with a plan. If ping pong’s not your thing, challenge me to a game of bowling, mini golf, checkers, go fish—something, anything—just show me that you want to have a good time.

My single girlfriends and I might all be very different, but we have one thing in common: We want a man who can let loose and have fun. Trust me, you will get that second date because you’re engaging her competitive side, and there’s something to look forward to. Good luck!

Next week: Jamie shares the Do's and Don'ts of the Next Day Text

Tags: getting-around-town-with-jamie-shupak, jamie-shupak, dating
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