How to suck at speed dating and four questions to overcome it

speed dating

“What do you do for a living?” It’s the seventh time I’ve been asked this question in less than an hour. My voice is hoarse from talking and I’m starting to feel like I’m at a rotating panel interview rather than a speed dating event at a lush bar in downtown Toronto.

Don’t get me wrong. I love my job and it takes up a big chunk of my life, but it’s not exactly the stuff that romance is made of. Similarly, my potential suitors’ descriptions of data networking, tax accounting, industrial equipment sales and quality control aren’t exactly causing a stirring in my loins.

Few things are less sexy than work.

Yet, every discussion, it seems, leads back to our day jobs.

I get it. Successful in our chosen fields, we think that talking about our career shows that we’re an independent woman or a man capable of providing a comfortable life or someone who, in fact, has a life.

But, here’s the problem. Talking about work at an event where you have less than five minutes with someone inevitably steers the conversation into the professional zone.

And, unless you are an escort or a porn star, sex and the professional zone rarely mix. Furthermore, only talking about work fails to give any sort of impression of what you would be like to hang out with outside of work and that fails to set you apart from your competition.

People don’t attend speed dating events to add to their LinkedIn network.

They attend in hopes of meeting someone who intrigues them enough to possibly want to get to know that person on a non-platonic level. Although I did gather a few business cards at the speed dating event above offered through, I failed to connect with anybody enough to want to date them. Consequently, the company gave me complimentary admission to a subsequent event.

This time, I vowed to change the game.

Before leaving the house, I came up with several non-work related questions and a script to steer the conversation in their direction. In short, it went something like this: “I’ve noticed that a lot the discussion at these things is about work, but I want to find out who you are beyond 9 to 5 so I have a kind of crazy question…”  Then, I took my questions to the event. This is what happened.

If you could have any super power, what would it be and would you use it for good or evil?

I asked this question of three of the 12 men at the event. Two said invisibility and one said he couldn’t imagine having a super power. When I pressed for more information about why, I learned a lot more about my “dates.” For example, that:

  • one would go behind the scenes in politics
  • another would go behind the scenes in the ladies change room and
  • the third couldn’t imagine being a super hero because he was a Gold Personality Type (“Golds are reliable but we aren’t very creative,” he explained.)

Overall, it weeded out the candidates very quickly – being a wallflower and lacking creativity is not a good match for me – but it did spur some interesting conversations.

If you only had one month to live, but unlimited finances, what would you do?

This question cut to the chase of what’s important in a person’s life.

The three men I asked this all answered the same: “see the world.” The sad part was each followed it up with “but that’s not possible now because…” As a dreamer and a doer, I gravitate to people who also make things happen, so this again weeded out the candidates, but at least it fostered some discussion about a shared interest (travel) which in turn made our five minutes together go a whole lot faster.

Tell me something you haven’t told anyone in this room and are unlikely to.

This was, by far my favourite question because it created a secret…  and secrets create bonds.

While one person skirted the question and started talking about his work (ugh!), the others’ responses made me want to get know them more. For example, one man’s confession that he wanted to help people die with dignity led to an inspiring discussion of how other’s regrets had motivated him to live a richer life and made me see him in a much more intriguing light.

Meanwhile, another “date’s” secret desire to be a stand-up comic, something I’ve been, made me want to help him reach his dream. (It helped that he was funny as Hell… if Hell was like the Hell on South Park, but I digress.)

Asking hypothetical questions isn’t for everyone.

At the start of the evening, I shared my approach with another women. She grimaced at the thought of it. “Oh no,” she protested “That’s not me.” For those on the cautious side, I recommend the best question I was asked all night:

“I’ve noticed in a lot of my discussions tonight that people are very busy. What do you do to unwind?”

It acknowledges work but then redirects to other interests without seeming too kooky.

Let’s face it. When you first meet someone – whether at speed dating, online or on the street – the main thing you want to know is how will this person make me feel?

The few people I eventually selected at the second Dateswitch event all made me feel like they might be fun to hang out with. None, however, gave me that impression by talking about their job.

If you want to stand out at speed dating, ask questions that get to know the person, not their C.V. And – unless you are an astronaut, international spy, Pulitzer Prize winning journalist, rock star, famous actor, or world-renowned blogger on the single life (ahem) –  save the career talk for the second date.

3 thoughts on “How to suck at speed dating and four questions to overcome it

  • March 24, 2015 at 8:59 pm

    A favorite question of mine is “What is the best give you have ever given someone?” I think generosity, and really enjoying being generous, is an important characteristic, so I like to hear someone talk enthusiastically about doing something to make someone else happy. Curiously, many people have a hard time answering that. Some from other cultures have told me they “don’t give gifts” but instead bake or serve food, and they almost appeared insulted by the question. Others had a hard time coming up with an answer. I thought that was telling.

    I also like asking people what *someone else* would say about them. So don’t ask someone what their ‘worst quality’ is, but instead, ask them ‘what would your Mom say is your worst quality?’ Wording it a bit better than ‘worst quality’ might be advised, but you know what I mean. Maybe ‘why does your Mom think you’re still single.’ That plays much better than simply the old and ugly ‘why are you still single.’ It’s also nice to see if people’s face light up or if it cringes when you ask about their mother/father/family.

    One of the things that’s best about the dateswitch dot com events in Toronto, in my opinion, is the host. I’m just sayin’

  • March 28, 2015 at 8:59 pm

    Interesting advice but I would really caution against asking about the other person’s parents or family. They may not have any. I lost my parents early in life and this would be awkward/uncomfortable if someone did this at a dating event.

  • April 1, 2015 at 12:12 am

    Having an interesting job is almost as bad as having no job as I always get the feeling that the ladies think I’m fibbing. When people ask about my travels I can’t help but tell the story of the time I got the “Dalai Lama’s Revenge” in TIbet from eating street food (beware the yak fried rice). So I stick with the tried and true, “Lights on or off?”.


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