The Thousands of Boys In Two Thousand and Nine (2009)

Every once in a while her friends nod and they listen as she updates them intimately on men who are flakes, men who are balding, and men who need Orbitz sweet mint gum. As the end of the year is near, and it’s almost 2010, she runs through the memories of the past year, of men who loved her and men who she loved not. She vows to do some things differently next year, to be better, smarter. But, the past is the past. You can learn things from the past. And, believe me, you name him, she’s gone out with him (or one of her friends has) in the past.


She’s gone out with “You Can Wear Heels” – a boy from JDate who was a contestant from Average Joe—and there was truth in advertising. She could wear her heels, and he was very average. She’s dated “Vom Boy”— a term coined for the boy that projectile vomited all over her bedroom floor at 3 a.m. In his defense, he did send her a dozen roses the next day. She’s been set up with “The Italian Stallion” by her over eager yenta-of-a-mother, a typical Jewish mother who totes one of those large black purses with all the essentials—Kleenex, hand sanitizer, Advil, assorted snacks, emery board, Filofax, and stack of her single daughter’s business cards. On some dates, she drank too much. On others, not enough. She’s had good dates and dates that ended in “Oh, my goodness!” She’s dated “The Picky Eater Who Doesn’t Eat Anything Green.” He only eats at three restaurants in the city: Striphouse, Nobu, and Cipriani’s. But hey, at least he picked up the check. She dated the boy that used to live in the extra bedroom in her new apartment, brought together by cosmic fate…and the power of Craigslist. She’s seen friends get back together with ex-boyfriends they had sworn off. She’s missed her own ex-boyfriend. She’s been all consuming, head-over-heels, can’t live without you in love. She’s had to heal a conflicted broken heart. She’s tried blind dates, JDate, texting, sexting, Facebooking, bbming. She’s telling the truth, here. She couldn’t make this stuff up if she tried.

She is so excited. She is so frustrated. She is 24. She is me.

As a twenty-something living in New York City, I’ve had my share of dating. My friends have had their share of hearing about my dating. My dates have had their share of reading about it. So, now, I will share the lessons I have learned while navigating the dating pool. It’s almost 2010. Let’s agree on one thing. Forget resolutions. Let’s make some rules. This year, your love life can be as ball droopingly awesome and fulfilling as you want. It’s up to you. So, here are my all-time favorites—some nuggets of wisdom gained.

One: You don’t give up. You get excited about dating. You know how talented and gorgeous and brilliant you are. Empty yourself of cynicism. Before a date, think to yourself: this date is going to rule. Have fun with it. Remember one thing. It only takes one. It only takes one good date (no matter how it ends) to remind us of why we bother searching at all.


Two: Be kind, but also rewind. If he’s not for you, he’s not for you. Don’t force it. The three date rule (see my previous article, “From Frog to Prince—The Three Date Rule”*) does hold true. Sure, give the guy a chance. After all, the “instant spark,” which has only been witnessed in romantic comedies (usually starring Sandra Bullock or Kate Hudson), is, simply, a rarity. Reacquaint yourself with reality and remember that it can take time to develop. If you take those fantasy dates from movies to heart, you’ll end up eating popcorn and Junior Mints alone on your couch. But, hey, let’s face it, if you really do not love the trailer, you probably won’t love the movie, either.

Three: Don’t settle. You will find someone that you want to be with, both out in public, and in the bedroom. The Manhattan dating ocean is chock full of good catches, so don’t be afraid to throw one back in and cast your line again if things aren’t working out. You shouldn’t have to keep up the pretence of being fully happy with someone if it isn’t all there. Imagine, years from now, all the excuses you’ll have to come up with to avoid sex.

Enjoying the sun

Four: Don’t stress. Either you will get married soon or you won’t; either you will massively screw everything up or you won’t; either you will go out again with that guy who promised he’d call but just continues to send awkward Evites, or you won’t; either you will sleep with your best friend and ruin the friendship, or you’ll fall in love and get married. Remember this. In the end, no matter what happens, you will always end up in the same place. Able to start back at the beginning. So, don’t stress, just enjoy.

Five: It’s normal. You can still think about your ex. You can still look at old pictures. You can still question your decisions. You can still have sex with a guy, even if you know you will likely never end up with him. It’s OK. It’s normal. We all do it. Don’t be too hard on yourself. Ideally, should you stop? Absolutely. But, you have to run your own race. When you’re ready (even if that’s not until you meet your next great love), you will be able to put that all behind you. Until then, just accept that it’s normal. We all do it.

Six: Be someone you can’t get enough of, and you’ll be someone he can’t get enough of. Yes, you can make him think you’re unavailable. Yes, you can make him think you’re not going to write a column about him. At the end of the day, the only thing you can control is your actions and who you are as a person. If he likes you, well, then that’s just great. If he doesn’t, you shouldn’t want to be with him anyway. After all, he should be chasing after you like Tyra on the search for America’s Next Top Model.


In writing this article, I was forced to examine my past relationships and my hope for future ones. I admit it; I have bouts of questioning whether I really believe it will happen for me. I also have moments where I am convinced that I am not worried at all. But, after looking back at my adventures in 2009, I’m seeing things differently. Dating, instead of seeming like a sometimes terrible, if at times, thrilling and exciting journey without end, is beginning to seem like something with a finish line. I don’t know when I will get to the finish line. I don’t know who will be there to greet me. But, now, I do think, at times know with certainty, that I will get there. It only takes one. I can do one. And so, who am I? How about The Picky Impatient Jewish Girl Trying To Look At The Glass Half Full?

Fine. I’ll take that. But I’m learning. I haven’t mastered dating. And I’m not sure who I will be next year. But, for now, I’m just me. So, take it or leave it.

The stories, men, and actions in this article did not all happen to me (but most did). Mom and Dad, I promise.


photo courtesy of The Bachelorette on ABC