If at first you don’t succeed…

Try, try, again.

But what if your first failure has you convinced that you can never succeed?

(This post is inspired by a comment on an article about a “love-shy” man who avoided women for years after being ridiculed once in high school.)

When I was about 10 years old, I went to a summer art course. They brought in a live model for us to draw the human form. I had never before tried to draw what people really looked like, beyond a stick-figure or smiley-face. The classroom was quiet and I focused hard on drawing the woman’s face, but it never did look quite right. I went home frustrated and was convinced that I had no artistic talent. In high school I chose music classes so I wouldn’t have to face up to my visual art incompetence.

In my 30s, I took a pottery class, planning to make one mug as a gift. Turns out that making mugs takes lots of practice, so about five years later, I had given every friend and relation a stack of misshapen bowls, and one friend got tiny mugs with too-thick handles. When the pottery teacher retired, I was just getting good enough to produce two or three matching dishes, and I had started to paint leaves and flowers on the sides.

Instead of finding another pottery studio, I took a break to learn to paint better pictures on the sides of my pots. The local art school required that I take a drawing class before the painting class. This was really scary and intimidating, because I knew I had no drawing talent – why bother trying?

Some of the drawing class exercises were very hard: Draw an object you can’t see, but you can feel it inside a cloth bag. Draw a live model very quickly, because they change pose every 2 minutes. And the one that felt most vulnerable: here’s a mirror, draw your self-portrait.

The drawing teacher was very encouraging. She praised what we were doing well, and we could ask how to fix the flaws in our drawings. At that art school, we were expected to keep trying, keep failing to get it perfect, keep facing our vulnerabilities, keep trying to improve. Practice, practice and more practice.

I took more life-drawing classes, where you spend three hours drawing the same model in dozens of poses, starting with 2 minute sketches, and gradually allowing longer periods for detailed illustrations. We sketched on cheap newsprint because the results didn’t matter – these were just warm-ups and exercises. We had to ignore our internal assumptions about body shapes, and observe the actual shapes and positions of a model’s limbs – which might be foreshortened or hidden – and translate that to one colour in two dimensions. I got used to seeing my own errors and not caring about the failures.

(I also got to see a lot of naked people. Of course the art school had rules about not touching or hitting on the models. You didn’t know who would be modelling until you showed up for class – maybe a muscular man, maybe a wiry woman. Regardless of whether I found the models attractive, I came to respect their ability to sit very still, and hold awkward positions. There was one guy who could do a handstand for a few minutes!)

Although my life-drawing skills improved over a few years, I never got good enough to reliably make my drawing look like the person in front of me. Sometimes they looked realistically human-shaped, but much older or younger or otherwise different than the human model. Likewise, still-life drawing didn’t come easily to me, though with enough time I could struggle to portray some objects realistically.

Meanwhile I was learning other art mediums and techniques. My frustration with realistic drawing pushed me to making abstract art. I got very creative and reasonably skilled at that. I have made, gifted and even sold lots of abstract paintings, collages and sculptures. I’ve learned photography too, for when realism is needed. Sometimes I get negative feedback (or more likely, people politely ignore my artwork) but that doesn’t stop me from making more.

So that first attempt to draw, at age 10, delayed my art career by about 20 years. I could have had a lot of fun making paintings in those intervening decades, if I had not discouraged myself with high expectations. I shouldn’t have expected my first drawing to get the shape quite right – nor should I have expected much from my 1000th drawing. Maybe drawing number 1001 looked better, but that’s not the point. I gave myself room to try and fail repeatedly before giving up. When I recognized that I won’t excel at the standard life-drawing techniques, I detoured into a form of art where I could succeed and enjoy the process.

In case I’m not already hitting you over the head with this analogy, what has drawing got to do with dating? If you were rejected once in adolescence, it would be sad to give up trying for decades afterwards. Social skills take practice, dating is going to be full of awkward failures. People will ignore you if they’re not into you. Find someone who encourages you through those vulnerable and insecure moments. Respect everyone’s body and soul, especially if they are naked. If the standard methods don’t work for you, try different approaches that might. If at first you don’t succeed, try, try, again.


Alana is the organizer of Connect2Hope.net, the founder of the Love Not Anger project, and the creator of the original "involuntary celibacy" support website in 1997. This post expresses her own views; she is not a mental-health professional or dating expert.
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