Gillian and Derek were in town for a friend’s wedding in October, so she booked me for their annual portrait session. Unfortunately, that week ended up being super rainy, but we made the best of it. They braved the cold at Cattle Point for some gorgeous evening light, then we headed to the Atrium to warm up at Habit, before taking some pretty shots on the rainy streets.

These guys were so much fun. They’re very playful, giggly, and skip and dance around randomly. It was a bit hard to keep up at times, but I survived, and got some pretty cute photos out of it.

Derek contacted me before their visit and said he planned to propose to Gillian several days after our shoot. He wanted to have it photographed because he knew that’s what Gillian would want. Sadly, I was heading to Ontario and wasn’t able to shoot it, but I got my frequent second shooter Gwen to take the photos (leaving the editing to me). I think she did a stellar job.

I love Gillian’s expressions during the proposal sequence. First she’s all confused as to why they’re standing on the rocks in the rain, then shocked, then totally overwhelmed with emotion. So sweet. Gillian was extra surprised when she noticed Gwen taking photos. Apparently hiring a photographer is out of character for Derek. They’d told me that his reward for our photo session was beer. I guess his reward for getting proposal photographs is marrying a beautiful redhead – and maybe picking the beer for the reception.

Here are some of Gwen’s photos of the proposal.

For the first shoot:
Hair: Conscious Hair by Elena
Makeup: Hollie from Prive Beauty Lounge