Taking Pictures of Strangers in the Streets

Walking up to a complete stranger and asking them if they would like to have a photo taken of them is a challenge for some people. This is exactly what Jessica Kobeissi set out to do, but she wasn’t alone. She decided to have the duo from Mango Street, Rachel Gulotta and Daniel Inskeep, join in on her escapades in the streets.

What’s the best way to get volunteers for this? The trio made some signs with poster boards stating “free portraits” which didn’t seem to work out very well. Asking strangers with a sincere approach while giving a compliment on their style or look worked a lot better and I would assume this would have the best chances of success if you wish to try this challenge out for yourself. 

Below are some of my favorite shots from the challenge.

I quite enjoyed watching the video to see how the three of them approached the strangers and worked with them to capture their shots. Everything was kept simple and they worked in the area where they came across the strangers. Having the strangers sign the model release did have one stranger walk away thinking it wouldn’t take as much time away, and I wonder how many others did the same. What are your thoughts on this challenge?

Images used with permission of Jessica Kobeissi, Rachel Gulotta, and Daniel Inskeep.

Log in or register to post comments



Work in group of 2 or 3 for safety. Getting model release is tough. Offer the strangers a photo file as a thank you.

Spike S's picture

I would never walk in a group, it can be intimidating to people. And what do you need a release for? Are you shooting street portraits for an ad?

Steven Boesky's picture

I was at a park recently and a mother and daughter were having problems with their own camera. I offered to help them and I did fix their problem. The daughter was beautiful and I asked if I could take some pictures of her. At first they seem reluctant, but I told them that photography is a passion of mine and I would send them copies of the photographs. The mother gave me the email to send them to which I did the following day. She returned an email to me thanking me very much for the beautiful shots of her daughter. I was nervous asking them, but I would do it again.

Geoffrey Wiebe's picture

I'm an introvert but when I decided I wanted to start learning portraiture a few years ago, I'd spend a day in the parks by the river offering a free digital photo in order to help step outside my boundaries. I would ask for an email address to send the photo to, and I'd give them the link to my Facebook page to confirm who I was.

My very first day doing this, someone called the police on me and accused me of taking photos if people without permission (which I wasn't doing). Thankfully I knew my rights in public and had a long, somewhat tense, discussion with the two officers that came by. They eventually agreed I wasn't doing anything wrong.

Oktawian Gornik's picture

I really enjoy taking pictures of strangers and dont remember anyone refused it. However, I dont do it so much anymore as I focused on studio photography, this is my favourite street photo of a stranger in Hong Kong, from last year.