Last Wednesday night I was sitting at a below ground bar in the East Village, a cash only joint without air conditioning, the waiter with skinny jeans and an accent, and a laundry list of beers on tap. I was waiting for one of my editors to arrive, one I had only communicated with via email and Twitter, and had yet to meet IRL (Mom, Dad, that’s “in real life”).

We had plans to workshop my old columns and brainstorm ideas for future ones. I knew he was a young, talented writer and editor, and from his Twitter avatar, had curly hair and a beard. What I didn’t know was that he would blow up my whole theory on young single guys, and serve as inspiration for this very column.

He straggled in a few moments later with all the makings of a typical young, single Brooklyn guy: small-framed, rock t-shirt and jeans, plus a non-cliché mellow vibe. Over a couple of draft beers and salty oysters this 24-year-old and I talked writing, careers, and dating. Not surprising: he lives in a house with a bunch of roommates (not all guys), loves checking out live music (any kind, but loves his hip-hop) and would like to meet a girl (but not just to hook up). Wait, what? He muttered the words and I nearly fell off the now sweaty bench I was perched on.

That same declaration would have zero shock value from a woman my age or older, but from this kid, I was dumbfounded. I know everyone wants to meet someone; I just didn’t think it would be a priority for a 24-year-old and his crew.


I tell all my single friends, you might not meet a guy at the bar tonight, but you definitely won’t meet one eating takeout alone on your couch. You have to put yourself out there. I know you’re tired, you feel fat, you have nothing to wear, drinks are expensive… so keep it interesting. Bars, clubs, and lounges are easy, but so are the women you’ll most likely meet there. And when you think about where your closest friends met their significant others, how many met at a bar? Out of my friends the count comes in at exactly one.

So with this long-awaited change of season, let’s also change our approach to dating. How about walking around the park or beach on a Saturday afternoon? You won’t have the three whiskeys to give you that boozy confidence, but women are more approachable than you think. Smile, say hi, offer a compliment (nothing creepy), or ask for directions or what she has planned for later. I know you’ve walked by at least 10 girls this week that you would have loved to talk to—in the supermarket, on the subway—so next time make a move, single guy. If she rejects you, who cares? You will never see her again. A good guy friend of mine told me a girl can smile at a guy in Duane Reade and walk out with his number. It’s that simple.

An even easier way is to sign up for a class. There are cooking or photography classes, wine tastings, art lessons, all places where you can assume that the women you’ll meet there have similar interests as you. Make sure to check sites like Gilt City, Lifebooker, or Groupon for deals on classes and then invite your friends. I wrangled a couple of my girls to go to this dating boot camp in a few weeks and then speed dating after that. Will we meet our future husbands there? Maybe, maybe not… but an old friend emailed me the perfect quote last week: “Dating is either a good time or a good story.”

I’m not out of ideas yet, single guy! Have you been to all the museums in your city? If you want a cultured woman, you have to participate in culture. How about look for a good book in your local library or Barnes and Noble? Go to the outdoor flea market or concert at Central Park. When I told my Mom about this column, she said go to the dog park, and if you don’t have one borrow your friend’s dog. (Mom, genius!) The place is swarming with women dying to tell you about the cutest thing Fido did last night. Bonus: someone who owns a dog is most likely responsible, compassionate, and likes the outdoors. If that’s your thing, offer to walk your neighbor’s 4-legged friend. Just don’t forget the poop bags.


I might make some enemies for saying this, but the gym seems like the perfect place to meet a woman. I should mention that I don’t belong to a gym, but I did just start taking spinning classes. My first thought was, there are a lot of cute guys here. My second thought was, maybe most of these guys don’t like girls. But still. These kinds of classes are breeding grounds for dates. If you’re there, you care about your health. You’re either in shape or want to be in shape. Again, similar interests. I know a lot of people don’t want to be bothered while getting physical, but if you think I’m cute enough to talk to with sweat dripping from my ponytail, just wait ‘til you see me after a shower and a blow dry. There’s so much to talk about too: how great the new Lil Wayne track is, how weird the guy on bike 3 looked, or, best yet, when you’re coming back for another class. Whatever she says, you’re already signed up for that same one; easiest date you ever scored.


I know your boss’ kid’s third birthday party doesn’t sound like the wild Sunday afternoon you were hoping for, but besides the obvious reason of some quality outside-the-office time with said boss, you should go. You never know who else might get dragged there. People ask me all the time how I meet the guys I’ve dated and the simplest answer is, I never say no. Book signing with an old work friend? Sure. Happy hour with cousin Frank from Florida? Why not? Oh, my neighbor has an extra ticket to a movie premiere? I’m there. Every barbeque, housewarming, engagement and birthday party, wedding and bar mitzvah, go! Be social and don’t forget what I told Miss Demeanor last week. It’s all about attitude, so make sure to uncross your arms and smile. Be open to the idea that this might actually be fun, and you might even meet someone. Maybe just a new friend, but that person could have a sister or best friend that’s cute and perfect for you.


Two of my close girlfriends met their now-fiancés through online dating. I know people have hang-ups about it, but these are two beautiful, successful, smart, sassy women. Not women who couldn’t get dates or couldn’t find men on their own. They were looking to expand their dating circles and they found two wonderful men and fell in love. If you want to follow their lead, grab a close friend to help create your profile, one that showcases your true self, physically and otherwise, and go for it. Let me know how it goes.

Next Week: Jamie shares what you can learn about dating and love from her 93-year-old grandfather.