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It came to my attention that my dear Timo and I were nearing our 4 year dating anniversary and I wanted to get him something special and memorable. We had previously decided not to give each other gifts because I am broke and we’ve been together long enough that we really don’t need to go all out on our anniversary.

Even with that in the back of my mind, I decided I wanted to get him something and I set my sights on a portrait by a street artist. Now everyone knows the easiest place to find a street artist in New York City is in the dreaded, the evil, the congested, the overwhelming Times Square (tourists love that place but locals abhor it).

So I grabbed a favorite photo of Timo and I, hopped on my bike, and pedaled off in the direction of my dreams. First mistake of the day: wearing a skirt to bike. I am not the most experienced biker so holding the blowing skirt down with one hand was not an option. So there I was, dodging traffic with my skirt flying up around my head.

I arrived in Times Square without any major mishaps and set off to find an artist. Many of these artists strictly do caricatures which I cannot stand. I don’t understand for the life of me why anyone would want their most recognizable and/or embarrassing feature exaggerated in a picture but I digress.

Finally, I found a group of three men who seemed pretty promising. Not only did they say they could draw a lifelike version of my picture but they had examples of their work to prove it (I knew it was really their work because one of them was drawing a portrait of a picture and it was breathtaking!). So I haggled the price of a portrait down from $80 a head (yikes!) to $30 for two heads and sat down to watch the magic happen.

Forty-five minutes later I had a giant portrait of Timo and I that looked like Timo and some random girl with a giant shnoz and a Jay Leno chin…lovely. As I begrudgingly dug around in my wallet for the $30, the artist told me I would need to buy a frame because the charcoal drawing would smear. Naturally the “frame” (a cheap piece of plastic surrounded by matting) was $20 because he “has to buy them himself.” Twenty freakin dollars. I knew it was bull but I needed that plastic cover and there was no other place in Times Square to get one. Mistake number two: I bought the damn matting for $20.

The magic happening

Knowing I had been hustled, I hurriedly paid the man $50 (my entire month’s stipend), grabbed the painting, and rode off. I got about three blocks away when I realized that biking with a ginormous picture in my hand was not going to work. Mistake number three: biking with ginormous picture in my hand. As I slowly pedaled with the picture precariously hanging on my handlebars, a car pulled in front of me and I tried to brake. Too late. I hit it and it sped away. With that, the biking ended and I walked the rest of the way home, sweaty, irritated, and discouraged.

Three hours later and $50 lighter I sat at home in my AC, the picture turned backwards on my mantle because it made me sick to look at. Good thing dear Timo is a good natured fellow who can manage my mishaps with a smile and an, “Oh honey, you’re book smart but you’re not very life smart.” Ahh, sweet nothings in my ear.

The lovely portrait now sits in his room…at his parents’ house…8 hours away from where he lives. It’s funny how the most expensive gift I’ve ever given him is also the most unfortunate. It may not have turned out like I pictured it in my head but this gift will certainly be memorable. Oh the things we do for love.

What the picture looks like

What the picture is supposed to look like