“You should go on 10 dates with someone before you sleep with them.”

10 dates, huh? My girlfriend and I looked at each other through the sides of our skeptical eyes when we heard this, one of the first pieces of advice dished out by our instructor at dating boot camp last week. You’re familiar with boot camps, one of the newer exercise trends promising to keep your heart pounding, muscles burning, and fat melting as you power through military-style drills. Same idea here, just aimed at shaping up a single woman's mind. Instead of some buffed-up trainer in tight Under Armour, our guru for the evening was a married 44-year-old professional matchmaker in jeans, a blazer, and a more than sufficient supply of hair gel.


“Don’t be a nun. But if you give too much away right off the bat the other person could lose interest. So on the first and second date, give a really good kiss goodnight.”

Again, my friend and I exchanged a wordless glance, but this time to say, “Okay, we can handle that.” Thus kicked off an hour of pretty personal Q and A, simple instruction on how to score a date, as well as the tougher follow-up: how to keep that person around and interested. Maybe this wasn’t such a waste of 19 bucks after all. I had gotten a few eye rolls over email when I first asked my single girlfriends to come to dating boot camp with me, but here was my rebuttal: we’re young and single in the best city in the world, so let's try it all, see it all, do it all, and meet everyone we can. Furthermore, if "what you put in is what you get out" is effective for dieting, exercising, and succeeding in your career, why wouldn’t it apply to love?


“Be the igniter—a fearless chick is a superhot chick.”

To all thirty women in the room (35% native New Yorkers)—and women everywhere, really—this was not news. Looking around, I noticed no women lacking in the confidence or attitude departments; they were there to learn how to work it. While Mister Dating Professor geared his self-described “four simple tried and true tactics to approach a guy” toward his female audience, these tips can just as easily be flipped for you single guys to use.


Number 1: Tell him you like his watch. Almost every guy wears one, they spend a lot of money on them, and so they want to talk about them. Tell him you’re helping a guy friend or brother pick one out, so would he please tell you everything about his. It’s the power of being personal and engaging in a conversation as if you already know him. Then, at the end, tell him this was one of the more interesting conversations you've had all week and could you please have his card to follow up on any watch-related questions that come up during your hunt. Boom, you’re in.

Guys: Follow the same course of action, but ask about her bag, shoes, or hair.

Number Two: Tell him, “You wear that sport coat well.” According to Mister Dating Boot Camp, this is different from saying, “I like your sport coat,” or, “You look great in that sport coat.” Saying that he wears it well speaks not only to your admiration of the garment, but more specifically to the way he wears it. You’re ever so delicately telling the guy, "I like the way you move."

Guys: Again, try this out on a woman’s bag or shoes. If you think you have the finesse, you can choose an item of clothing, but tread lightly because if you come off sleazy you won’t get another chance.

Number Three: Tell him that he smells good. Or, in your case, single guy, that she smells good, that you like her perfume. This struck me as a bit bold, as you’d not only have to get pretty close to smell me, but the situation could also get creepy fast. I actually don’t wear perfume, so if you tried this on me you'd either be  digging the fruity scent of whatever body wash was on sale at Duane Reade this week, or you’d be lying. For every other woman on the planet: this could work if you’re in close quarters in a bar, squeezing by her to get a drink, but it still seems risky. I’d go straight to the last tactic.

Number Four: Just say hi. Mister Matchmaker calls it getting a good return on investment. Basically, what you can gain (everything!) minus what it costs you (nothing!) makes saying hi the best investment you can make. If you see a woman in line at Starbucks and you lock eyes for a moment, smile and say hi. This is right on par with what I said a few weeks ago: I know you’ve walked by at least 10 girls this week that you would have loved to talk with—in the supermarket, on the subway, wherever. Next time make a move, single guy. If she rejects you, who cares? You will never see her again. It’s a numbers game. The more people you say hi to, the better your chance of there being one that smiles and says hi back.


“Tell them you’re dating other people. Don’t hide it. We want to know other men want you and find you attractive.”

While I agree with our beloved teacher that you should be open about dating other people, for me it’s much more about the honesty of the gesture—being forthcoming about where you stand with this person and whether you’re looking for a relationship—as opposed to the game he was encouraging us to run. He told a story about asking his wife out for the first time and her saying, “I’ll throw you in the rotation.” It provoked the competitive side of him and made him want to date her even more. Then he could show her—and, I think, more importantly show himself—that he could get her to dump the other guys and date only him.

My advice: just don’t ever ask how many people the other is seeing. Not only does it not matter, there’s also no upside. Whatever number you hear is going to make you upset.


“Leave the labels for your clothes, not on us.”

Now Mister Hair Gel was speaking my language. He said there are questions you should never ask the other person: Where do we stand? What are we? What’s going on with us?

Throw those questions in a dating coffin and never utter them again. They’re awkward, frightening, and even a little pushy. Try this: just roll with it. A forced commitment is one that won’t last. Let a relationship happen naturally.


“We have time for one more question,” the instructor said. I shot my hand in the air. This had been bothering me since we sat down. “Why aren’t you wearing your wedding ring?”

“I lost it spinning it on a table at a Dunkin' Donuts.”

“How long have you been telling that story?”

“Six weeks.”

Next week: Jamie discusses whether nice guys finish last.