The art of dating

Dating. For some that’s a very scary idea. For others, they love the thrill. Dating has a lot of similarities with acquiring art, whether you want to hook up or are ready for a long-term relationship.  

In the way that you would ask a friend their opinion on your newest love interest, I am often asked about how best to purchase art, whether the art is good, will it be a good investment, etc. Art critics, historians, curators, dealers, gallery owners, and appraisers all have varying opinions on what makes art great or makes a good investment (which are not always the same thing, by the way). I don’t intend to talk here and now about what makes great art or what is sure to be a brilliant investment, but I do want to tell you a little bit about how you might go about looking at art that you are considering for purchase. It can be like looking at someone you might want to date.

My first question to you is, did you do a double take? Have the urge to look deeper into their eyes? Or perhaps want to look them up and down? Sideways? Get them to smile and see what sparks?

boy standing in the water at sunset on the beach in cancun
Alone. Canon R6. Cancun. December 2021

Art provokes introspection and inspires contemplation and in turn,
creates a new observer each time. 

But you might protest and say “Wait that’s all about just how it looks…. yeah, an artwork might look nice or good or amazing, but don’t I want to be a bit more discerning and buy something that is going to increase in value?” Short answer: Sure. Then how will you know if its value is heading north? Another short answer: You don’t.  What’s more important to ask; do I want to live with this artwork for a long time? Because if it doesn’t actually ever go up in value (though serious artwork (and some not-so-serious too) does tend to go up in value over time) at least you will have enjoyed the work while you were living with it. If its value does increase substantially then that’s a bonus and you lucked out! Want a sure thing? Choose something you like.  One way or the other you will get something out of it. So go with what grabs you. It’s as simple as that. 

So how do you know if you really like it? How do you know if this is something that you think you are going to want to have in your home for years and not just tempted by nice biceps or long legs? That’s the real question…do you want to live with it? For years? Maybe decades?  After all, you are just meeting each other for the first time. Do you want to meet again? If you are not sure, that’s okay. Art doesn’t always have to make a good first impression. Sometimes after getting to know it for a little bit and learn more about it—get to know each other, our pasts and how we got to this very place and time, we become enamored. You might need to talk a bit on this first date and see your comfort level—do you want to know more? Has your curiosity been piqued? Do you feel as if there is any chemistry? If your answer is No, or you have no response or feeling, then just move on.  Don’t spend any more time and don’t waste your money.

Want a sure thing? Choose something you like.
ONE WAY OR THE OTHER YOU WILL GET SOMETHING OUT OF IT.

Encasement IV & V.
Ink on Plexiglass

If your answer is Yes, and the artwork evokes both immediate and subsequent responses, then it’s time to ask yourself a few more questions: What’s that response I’m feeling right now? Am I happy? Sad? Excited? Angry? Perplexed, Upset? Does it make me joyful? Do I feel the urge to smile or giggle? Did my eyebrows just go up? Does this work disturb me? 

Take the time and make the effort to ask yourself these questions. You will be so glad you did. Knowing where you stand right now can save a whole lot of time and effort and money later down the road.


Once you’ve honestly answered all the above, the next question is Why? Why do I have that particular response? And that is the most difficult question to answer.

If you can delve into that one you will learn things about the artwork and maybe yourself too, that you might never have known. Because that question involves soul-searching and understanding your response to what’s going on in the piece. That’s one of the many qualities about good art…it makes us look inward and having looked inward we look at it with different eyes the next time, and so we look inward again, and again a new view, new perspective, new “AHA” moments. Art provokes introspection and inspires contemplation and in turn, creates a new observer each time. 

Art doesn’t always have to make a good first impression

small oil painting of trees on a golf course
Study for Beyond the Clouds. Oil on unstretched canvas. 11″ x 14″ October 2021

Many people will say that great art is there to elicit a response and that even if you hate it and hate it with a passion, the art succeeded because you hated it with a passion. The art elicited a response as a result of you engaging with the work. I can’t say that I agree.  While studying at the Ontario College of Art a number of years ago, I remember looking at the work of a sculptor, a high realist, who showed us views of body parts like pieces of meat at the butcher. There was a certain seductiveness to these pieces—they were so perfect, so real, so disturbing. And yes, it was unsettling to engage with these pieces, but did that make it great? I debated endlessly with my profs, Dave Pellettier and George Boileau, about it. And I believe I swayed them a bit in saying the exhibition was an exercise in voyeurism and fabulous technique. Yes, we got involved and riled up, and we certainly did engage with it. But it was not great art.  

icy/slushy ground thawing underneath foot prints
It’s in Our Nature V. Canon R6. 2021

And that brings me to the next point… engaging with it. Does the artwork make you want to look more? See what’s behind the proverbial curtains, under the hood, kick the tires? If so, wonderful! You may be ready for a second date! How can you be sure? Well, take a pause. Walk around the gallery. Close the magazine or go to another browser window. Close your eyes for a few minutes… want to see more? Have a second look. Just as good? As engaging? As fun? Then try some acrobatics… try to see the work upside down, or from a far angle…if you can’t do a headstand, or don’t want people staring, then turn the work upside down, take a pic or a screen shot and look at it sideways, backward… is it still exciting? Make you want to see more? If you know after these first looks that you would like to get to know this artwork again that’s a good sign that you are ready for a second date. You’ll know it in your gut. If the next morning you have no desire to call, or see that work again, perfect. You just saved yourself some trouble and maybe a whole lotta bucks! If however, you are thinking dinner and a movie, now might be time to get out your wallet.

Next time I’ll talk about Getting Serious and looking with a critical eye for beauty in art, while exploring if beauty is a necessary component of what makes art great.

sunset photo of masked boy jumping off a huge chair
Wracked. Canon R6. August 2021

sunset photo of masked boy jumping off a huge chair
Purgatory. Canon R6. August 2021
sunset photo of masked boy jumping off a huge chair
So Done. Canon R6. August 2021