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Engagement Session in the City

January 22, 2021

Liane and Victor wanted a photo engagement session in downtown Toronto and we certainly hit some major hot spots of our city! Osgoode Hall is one of my favourite non-permit locations where you have a beautiful mix of nature and architecture. It can be busy with weddings on the weekends, but photographers are usually pretty fair when dishing out the sweet spots. 

A candid approach to Engagement Sessions

Our candid approach to engagement shoots allows couples to be as natural as they can be in front of the camera. For some people, this is their first time being photographed professionally so it can be daunting. Engagement shoots are a great time to practice being the focus, listening to direction, and being as natural as you can! Photographers and clients build a rapport shooting an engagement session and the purpose isn't just for cute photos - it is to prepare for the real deal on your wedding day! 

Engagement session Photo Games

Some people need more direction than others, and that is seriously okay! Practice makes perfect, right? My go-to practice shots will involve asking my couples to hold hands and walk towards something. Alternatively, we will play a "shout-it-out-game" that instigates laughter or tears. In good time, you will eventually forget the photographer is even there! 

Engagement session

People often underestimate the beauty of the city and think that natural settings are the "go-to" when allocating the best photographic scenes. I highly encourage my couples to find a non-permit location. Choose somewhere that is not over-saturated with tourists and somewhere that has a specific interest or activity. Getting couples to "do" something like go on their daily dog walk, get ice cream or riding rides at the EX, are all examples of activities where your goal is to "do" something. These are often very effective in photographs because you are in a natural element. Going out just to be photographed can feel contrived and forced for many people.  

Make it meaningful to you

Not all sessions are like that though, and that is truly okay. Like Liane and Victor, they chose spots that were meaningful to them. The parking lot in Kensington was my favourite because it's off the beaten path. It was quiet and intimate and allowed them to relax more than the City Hall environment where they might have 20 on-lookers. Pick a location based on your personality and what will make you more comfortable. After all, it isn't every day you have a commissioned photographer follow you around while you express actions of love. 

xx - april

Liane & Victor, an engaged couple, kiss while a streetcar zooms by in the background.

Liane and Victor wanted a photo engagement session in downtown Toronto and we certainly hit some major hot spots of our city! Osgoode Hall is one of my favourite non-permit locations where you have a beautiful mix of nature and architecture. It can be busy with weddings on the weekends, but photographers are usually pretty fair when dishing out the sweet spots. 

Engagement Photo Session in downtown Toronto with Liane and Victor in a seated embrace on one of the benches in front of, Osgoode Hall. Photographed by Olive Studio Photography.
Engagement Photo Session in downtown Toronto, with Liane and Victor, photographed by Olive Studio Photography with Liane and Victor holding hands outside Osgoode Hall.

Engagement Photography session in downtown Toronto, photographed by Olive Studio Photography, with Liane and Victor hugging.

Downtown Toronto Engagement Photography Session, Osgoode Hall Engagement photography session, Osgoode Hall couples, Osgoode Hall memorable moments, fall colours Osgoode Hall

Romantic engaged couple, engaged couples Toronto, romance at Osgoode Hall, Downtown Toronto nature and architecture, autumn leaves, engagement photo session by Olive Studio Photography
Cute engaged couple kissing at Osgoode Hall, yellow autumn leaves, nature and architecture, Toronto nature and architecture

Practice Makes Perfect

Our candid approach to engagement shoots allows couples to be as natural as they can be in front of the camera. For some people, this is their first time being photographed professionally so it can be daunting. Engagement shoots are a great time to practice being the focus, listening to direction, and being as natural as you can! Photographers and clients build a rapport shooting an engagement session and the purpose isn’t just for cute photos – it is to prepare for the real deal on your wedding day! 

Engaged couple embracing, couple embracing, Osgoode Hall engaged couple,

Photo Games

Some people need more direction than others, and that is seriously okay! Practice makes perfect, right? My go-to practice shots will involve asking my couples to hold hands and walk towards something. Alternatively, we will play a “shout-it-out-game” that instigates laughter or tears. In good time, you will eventually forget the photographer is even there! 

Engagement Photography Session in Downtown Toronto, field of yellow autmn leaves, Toronto in the fall

Engaged couple playing piggyback on a rooftop in Kensington Market in downtown Toronto while being photographed by Olive Studio Photography.
Toront skyline, couple on rooftop and view of Toronto skyline, engaged couple embracing on Toronto rooftop

Create an Action

People often underestimate the beauty of the city and think that natural settings are the “go-to” when allocating the best photographic scenes. I highly encourage my couples to find a non-permit location. Choose somewhere that is not over-saturated with tourists and somewhere that has a specific interest or activity. Getting couples to “do” something like go on their daily dog walk, get ice cream or riding rides at the EX are all examples of activities where your goal is to “do” something. These are often very effective in photographs because you are in a natural element. Going out just to be photographed can feel contrived and forced for many people.  

our corner of Toronto, Toronto rooftop, romantic Toronto rooftop, engaged couple embracing on Toronto rooftop, Toronto rooftop architecture

Make it meaningful to you

Not all sessions are like that though, and that is truly okay. Like Liane and Victor, they chose spots that were meaningful to them. The parking lot in Kensington was my favourite because it’s off the beaten path. It was quiet and intimate and allowed them to relax more than the City Hall environment where they might have 20 on-lookers. Pick a location based on your personality and what will make you more comfortable. After all, it isn’t every day you have a commissioned photographer follow you around while you express actions of love. 

xx – april


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Olive Studio is a documentary based photography studio, specializing in unique, intimate and off-the-beaten track weddings. Our candid shooting style allows for couples to...
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Liane and Victor wanted a photo engagement session in downtown Toronto and we certainly hit some major hot spots of our city! Osgoode Hall is one of my favourite non-permit locations where you have a beautiful mix of nature and architecture. It can be busy with weddings on the weekends, but photographers are usually pretty fair when dishing out the sweet spots. 

A candid approach to Engagement Sessions

Our candid approach to engagement shoots allows couples to be as natural as they can be in front of the camera. For some people, this is their first time being photographed professionally so it can be daunting. Engagement shoots are a great time to practice being the focus, listening to direction, and being as natural as you can! Photographers and clients build a rapport shooting an engagement session and the purpose isn’t just for cute photos – it is to prepare for the real deal on your wedding day! 

Engagement session Photo Games

Some people need more direction than others, and that is seriously okay! Practice makes perfect, right? My go-to practice shots will involve asking my couples to hold hands and walk towards something. Alternatively, we will play a “shout-it-out-game” that instigates laughter or tears. In good time, you will eventually forget the photographer is even there! 

Engagement session

People often underestimate the beauty of the city and think that natural settings are the “go-to” when allocating the best photographic scenes. I highly encourage my couples to find a non-permit location. Choose somewhere that is not over-saturated with tourists and somewhere that has a specific interest or activity. Getting couples to “do” something like go on their daily dog walk, get ice cream or riding rides at the EX, are all examples of activities where your goal is to “do” something. These are often very effective in photographs because you are in a natural element. Going out just to be photographed can feel contrived and forced for many people.  

Make it meaningful to you

Not all sessions are like that though, and that is truly okay. Like Liane and Victor, they chose spots that were meaningful to them. The parking lot in Kensington was my favourite because it’s off the beaten path. It was quiet and intimate and allowed them to relax more than the City Hall environment where they might have 20 on-lookers. Pick a location based on your personality and what will make you more comfortable. After all, it isn’t every day you have a commissioned photographer follow you around while you express actions of love. 

xx – april