The first date questions men want to ask, but won’t

April 3, 2012

Whether the traditional intimate dinner for two or more adventurous affair, first dates are a time of heightened anticipation and excitement. The giddiness that women might feel before and during a first date is almost undoubtedly accompanied by nervousness, the fear of awkwardness and the possible furtive mapping of escape routes. While there are certain elements of the date that are within your control, like picking out a killer first date outfit, they are far outweighed by the myriad of things that are not. There is so much that is undetermined about that initial date: whether or not there will be a connection, whether a potential new relationship is unfolding or whether an entry on My Very Worst Date is forthcoming. The potential of the date is still debatable until that final goodnight kiss, or lack thereof.

First Date Qs

While this uncertainty might inspire a Virginia Woolf-esque internal monologue, there are questions that, unbeknownst to women, men too are just dying to ask. If men are dying to ask their date questions, why don’t they just ask them? That simple! Actually, you may think it is. But there are several reasons why guys will keep their mouth shut. Modesty and embarrassment may be some of these reasons, and then there is also the fact that they do not want to have their date running and screaming in the other direction after being asked a ridiculous or even perverted question.

Surveying a number of men between the ages of 19 and 25, I posed the question: What is one question that you would want to ask on a first date, but wouldn’t?

The Big Three: The unsurprising and most frequent questions guys wanted to ask.

  • How many sexual partners have you had?
  • What’s the chance I’m going to score tonight?
  • Do you have any STIs/STDs?

The Ice Breakers: The questions designed to flatter or put at ease.

  • What is your relationship like with your family?

“I am really close with my family and so I would like to know what her relationship with her family is like” – Peter Clarkson, third year political science student

  • Is there anything you’re really good at that no one else might know about?
  • I think you’re cute, but I have no idea why you like me. How did I get this date?
  • What could I do to make this date go better?

“Most first dates are tentative and kind of awkward because neither person knows the other. What could either person do to relieve this awkwardness and make the other person more comfortable? And that goes both ways.” – Jeffrey Gupta, fourth year business student

  • What are your biggest indulgences?
  • Where do you see yourself next year?

The Somewhat Invasive: The “turn your head and cough” questions.

  • Do you have good credit?
  • What is your family disease history like?
  • What’s the biggest penis you’ve ever had?

I’ve always wanted to ask this, but I think it stems from insecurity” – James Anderson, first year (undecided) student

  • Why do you –insert peculiarity here-?
  • Have you ever been with a girl?
  • Do you practice safe sex?
  • What colour panties are you wearing?

The Job Interview: The “when can you start” questions.

  • Are you looking for something short-term or long-term?
  • How much money do you make? Want to make?

“I would want to stay away from a question involving their financial goals; it’s definitely not first date subject matter.” - Shane Raucsh

  • What happened in your last relationship?

When it comes to first dates, getting to know your date in the most organic way possible is an integral part of creating an enjoyable experience. The less pressure you place on yourself and your date (by focusing more on present enjoyment than the possible future implications), the more likely you are to come off as comfortable and genuine. If all else fails, refrain from asking the majority of the aforementioned questions on the first date and the likelihood of getting a second date increases exponentially.