I had the pleasure of spending the evening a day ago with Waseq, a talented photographer visiting for the week to attend a study session here in Singapore. Check out his beautiful photos here. Over coffee and tea that evening at Killiney, we decided to hit the streets of Orchard and get us some portraits of strangers. Typically shooting candids, I do not often approach people to ask for a portrait, so this was a fun experience to go out and try our luck.

Asking someone for a portrait is no easy matter. For a single guy, it’s a lot like mastering a pickup line to approach a girl at the bar. Avoiding a drink in the face or a face slap while initiating a dialogue is the goal. This is no different, except the desired outcome is NOT a date, but a beautiful portrait. Waseq had the technique nailed. Immediately after leaving the cafe and making our way to the main road, he was already approaching people with a smile, asking politely for a portrait. Together, we asked a number of people and introduced ourselves like this, “Hi, sorry to interupt, my friend and I are doing a series of portraits of people we meet this evening around Orchard. If you have a minute to spare, we would like to take your portrait, and in return we will email you the photo to keep. Would this be alright?” We had many people telling us yes! We also had several people politely declining.

I say politely in that no one gave us any angry comment or gesture when turning us down, and we did not try to push our luck too hard, we remained passive. Waseq has a great smile, and we both kept smiling as we asked people, while keeping our hands on our cameras and doing our best not to look intimidating. After our subjects agreed to the shot, we assured them it was for a personal art project and we would not sell any of the photos. It was great fun and our subjects had a good time and were genuinely happy to have their portraits taken. We also tried offering a compliment first before requesting a photo, along the lines of, “Wow, you’ve got great style, we noticed you walking this way. We are doing a series of portraits of strangers we meet in the street. Would you mind if we take your portrait?” Sounds REALLY cheesy, right? It works though.

Doing this with a friend helps a LOT. This is really challenging when doing it alone, but I think when there are two or three people, it looks legit that it’s genuinely for an art project and not some shady thing. If you’re out doing it alone, make sure you’re well groomed and dressed nice. Nobody wants their portrait taken by some messy dude in an old t-shirt and ragged pants, wear something nice and always smile, even when getting rejected. You may see these people again later, so good to keep it nice and peaceful and friendly. After seeing you around for a while taking portraits, the ones who say no today might just approach you and say yes another day.