Hey! You there, with the awkwardly tied tie and the sweaty palms! Am I right in thinking that you’re getting ready for a date? Maybe even a first date?
You poor sod.
Dating is not something that they teach in schools. Women are at an advantage here, having been assailed since puberty with movies, TV shows and magazine articles illustrating every possible dating scenario and offering tips. Most teenage boys did not pore over Seventeen or watch “Pretty In Pink” eleventy million times.
A single friend, Craig, confirmed our suspicions:
“Grown men are clueless about dating because dating is boring and stupid,” he writes. “Men tend to know a lot about things they find interesting, like hockey and wars. Dating is not interesting. Dating is like cricket in North America; we don’t know the rules because we don’t care about the game.”
It appears that unless they are natural born Casanovas, some gents can be a touch clueless when it comes to dating.
We consulted dating pro Gary Wilson of Eligible Inc. for his advice and handholding for those less schooled in the art and ritual of the first date.
“Many men don’t appreciate the fact that our every move is being assessed for future suitability. So prepare in advance,” says Wilson. “That means giving consideration to the venue, the timing and how you’re going to engage this woman for the first time.”
Part of this preparation is figuring out some conversation topics ahead of time. Come up with three or four potential conversation boosters in case the dreaded Awkward Silence descends.
“A very common complaint from women after a first date is that he did nothing but talk about himself. Bad move,” says Wilson. “The more he asks about her, showing sincere interest, the more wonderful she’ll feel and the more likely he’ll get a second date.”
A carefully selected venue is also key to a smooth evening.
“I recommend a quiet lounge or bar. A glass of wine can calm first date jitters and lend to a more relaxed experience.” Wilson cautions against the painfully clichéd dinner-and-a-movie date. Save that for later, when you’re more comfortable with one another.
Oh no! The bill has arrived! What to do?
“Without a doubt, the man pays for the first and likely the second date. Period.”
Wilson adds that a classy move for a woman would be to treat on the third date, or at least contribute in some way. If you finally go for that movie and buy the tickets, she might offer to treat you to something salty or sweet from the snack bar. (Dudes, that is not a euphemism.)
Christine Hart, author of The Art of Living a Flirtatious Life, has a different opinion on the tricky “who pays?” question.
“It should always be the asker,” she says. “It makes it easy.”
She goes on to say that lack of funds shouldn’t stand in the way of wooing a lady.
“It doesn’t matter what he does for a living, he can take a girl out on a lovely date. He can treat her to a tea and a really nice piece of chocolate cake and they can share it. She doesn’t need to be whisked off to Italy for a weekend… a woman just wants to feel seen.”
Above all, the first few dates are about getting to know the other person.
“I always recommend to men to go slow and get to know the woman,” Wilson says. “Think of it as a journey where you get to discover some amazing things about someone else and maybe yourself. Less is more in the beginning. Let things unfold naturally while you enjoy some great dinners, fun activities and hopefully the company of an incredible woman.”