Your First-Date Boot Camp
So you scored the number of the beauty at the party. Congratulations. Now comes the hard part – winning her over on your first official outing together.

April 11, 2012

So you scored the number of the beauty at the party. Congratulations. Now comes the hard part – winning her over on your first official outing together.

What happens during that critical meeting will nudge her towards a close encounter – or towards the door.

To see what works and what doesn’t, I created my own first-date crash course, cramming 10 of these sublimely stressful adventures into 10 straight days. I went out with women I’d either met on my own or been set up with through friends or online.

We had coffee, went out for dinner, took in a movie and, a few times, got slightly
liquored. After each encounter I checked in with my advisors, a team of seasoned dating experts, to dissect what had happened (or what hadn’t), and why.

In some cases, I swung and missed. In others, I made it well past first base. Though it wasn’t always pretty, I uncovered a few key secrets to turning first encounters into second, third and possibly more outings. Read on, and date like a man who’s been there before.


Poor Tiana. This cute brunette actress, a friend of my friend Dave, was my unfortunate first date. We met for dinner at a French restaurant I’d never set foot in
before. “So, what’s good here?” she chirped. “To be honest, I don’t have a clue,” I replied. Her blank look spoke volumes. She wasn’t impressed. And the poor service didn’t help. I felt foolish. The venue was one aspect of the date I could control, and it was proving to be more of an annoyance than an aphrodisiac. After dinner, Tiana said she had to meet up with some friends and split. Ouch.

I turned to psychologist Paulette Kouffman Sherman, author of Dating From the Inside Out. “We’re at our best when we’re comfortable,” she said. “So go where you’ve been before – even with other women.”

A couple of nights later, I took Mandy, a book publicist I’d met at a party, to my favourite burger joint, a classic bar. I’ve eaten there often, so I had no problem scoring a great table. When she asked, “What’s good here?” I replied, “You’d be crazy not to try the béarnaise burger, medium rare, with sweet potato chips and a bottle of Amstel.” She did just that, took one bite of the burger, and raved, “Oh, wow, this is amazing.”

It wasn’t long before our eyes were locking and our hands were wandering. Afterwards, she asked, “Want to walk me home?” That’s where we wrapped up our evening.

Your battle plan

“Most men don’t do this, but creating and repeating successful date templates is critical,” says Eric Ivy, author of The Dating Matrix. Befriend the maître d’s and bartenders at your favourite places, he says. They can hook you up with prime tables and drinks to help you impress.


First-date conversations follow predictable lines – where you’re from, what you do for
a living. I stuck to this script, but on one date, out of boredom, I geared things up.
It began when I asked Janelle, a public-relations rep, what, as a child, she wanted
to be when she grew up. Her response – TV presenter – not only gave me insight into her personality, but also provided an opening for me to share my childhood dream: at age 12, I’d started a band called Stiff Lederhosen. We made one recording before I realised I could neither play guitar nor sing with any skill. Janelle laughed, so I followed up with more fresh questions. We talked about what kind of animals we’d like to be, what kind of superpowers we’d love to possess and other whimsical topics. These unexpected questions allowed her to open up. And because the questions grew increasingly flirtatious, our chemistry bloomed.

Your battle plan

“Every man I know who’s good with women has a host of stories, questions and jokes that elicit good responses,” says Charles Orlando, author of The Problem With Women… Is Men. “Meeting and dating takes time and is competitive,
so come prepared.”


One of my best first dates was with Jamie, a writer I met on a dating website. I asked Marty Savarick, author of 101 Ways To Stop Hating Dating, how to keep things interesting on a date. “Try changing locations midway through. It will reenergise the mood and create a sense of shared adventure,” he said.

My first thought when I met Jamie was, We’ll be lucky to move past one drink. Other women I’d met with her look – tiny, blonde, cocktail dress – were a bit boring. But she proved to be edgier than I’d expected. “I may look like a vapid Cape Town girl, but inside I’m smart and overweight,” she joked. After some drinks at a hotel bar, we were both restless, so I suggested moving to a cool little restaurant famous for its delectable Portugeuse sausages. She loved it. We ended the evening with a kiss, and went out three times in the following two weeks.

Your battle plan

Set up locations so things flow from casual and fun to romantic and intimate, suggests Christian Hudson, creator of the dating website No need to mention the second spot when you set up the date – just have it in your back pocket should the situation arise.


Ever been on a date that you thought went great, only to never hear from the girl again? I found myself on the other side of this scenario thanks to Lindsay, another woman I met through an online singles network. She was cool, but I wasn’t physically attracted to her, so I found myself smiling tightly and chuckling a lot, just to be polite. After an hour, I said I had to head out. The next day Lindsay emailed me a sweet note. I never wrote back.

But I was bothered by my date with Janice, a website editor who seemed really into me only to leave after an hour for a work call – at 9pm. According to sociologist and relationship expert Julie Albright, my experience with Lindsay mirrors what many women go through on unsatisfying dates.

“Women generally smile a lot to mask negative emotions, so she may do that during your long, drawn-out story that she actually finds boring,” Albright says.
Your battle plan To find out if she is truly into you, look for signs that actually mean something. “Drinking lots of alcohol, touching you, heavy eye contact and leaning in towards you are all good signs,” Hudson says. “If she ignores her cellphone, that’s
a great sign.” Receiving these signals? Try touching her hand. If she doesn’t pull back, then you’ve probably won her over.

It was, of course, a terrific 10 days. I landed second dates with five women, and three I really liked extended beyond that. I owe this to my support team’s killer tips, plus one or two of my own.