Tina is a good friend of mine. We were both living in the same neighborhood in L.A. when we worked at True/Slant, a now defunct publication that was mostly acquired by Forbes. I moved to New York City not long after that, and Tina ended up moving here a short time later, too.

At dinner one night, I asked Tina if she'd let me shoot a few photos of her, just for fun. Since winter is still in full force in NYC, I checked the weather for the coming week to see which day would be best.

Friday? 50 degrees and potentially sunny? It's not going to get any better than that!

A day or two after that dinner, Tina told me that one of her friends is a make-up artist, so she could have her make-up done for the photo shoot. I thought, "Uh oh. I was hoping it'd be casual, but if she's going to have her make-up done, I guess I'm going to have to really shoot some killer photos.


Friday came around and the weather was just awful. It was freezing cold, incredibly windy and cloudy with a good chance of rain. Any light in the city would be flat and dull, so I packed a flash unit just in case.

When I met with Tina on Friday, she was having her make-up done by a make-up artist at the Current TV building in Midtown West -- way west near the water. As I walked toward the building, I started looking around for a place to shoot good photos. I wasn't very happy with the light already, but what's worse was that the surrounding areas were under construction and very ugly. It just wasn't looking good!

So when Tina's make-up was finished, her make-up artist said that we could get roof access to the building. Perfect! I can just get cloudy, dramatic skies behind Tina and I wouldn't have to worry about the construction and cranes. Wrong! The roof itself was cluttered with satellite dishes, vents, air conditioning units and hardly any clear or clean spots to serve as the backdrop for Tina. To make matters worse, it was incredibly windy and cold. Our jackets and bags were being blown all over the place, and her great hair was being whipped left and right.

At one point, we nearly decided to give up. She was cold, so it was getting a little hard to direct her, and I could hardly feel my hands anymore. The tiny little rooftop offered few options in terms of good pictures, so why not call it quits and try another day? But before we left, I decided to pull out my speedlight to see if I could at least darken the skies or give good separation between Tina and the cluttered background.

It's not the best photo I've ever taken, but it was probably the best I could do given our conditions. And I'm glad that Tina was such a good sport about it! Shortly after taking this photo, we found some warm comfort food and cold beers. Thanks again, Tina!