Winter Engagement Photography | Cassandra & Jared

Winter Muskoka engagement photos


The photo gods did us a solid the night before this shoot sprinkling an ever-so delicate dusting of snow creating a wonderfully whimsical winter engagement session with my new friends from Muskoka.  From snow-graced pathways to the Christmas tree field and on to Barnstormers craft brewery – oh twist my arm!

Cassandra and Jared have an awesome engagement story to tell so I’m just going to get the hell out of the way and let them tell it.  Girls, you’re going to want to hear it – and guys, take notes.

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Winter walk engagement photosPre-wedding engagement wedding photoHot chocolate engagement photosHot chocolate kiss photo
We met in Ottawa at the Algonquin College Residence in 2008. We became best friends, started officially dating in March 2009 and got engaged in October 2016!

Snow pre-wedding photo

Cassandra: I honestly don’t remember an official “first date” because we had become best friends and just spent so much time together going to random places, dinner, movies with all our friends. I do however remember the first actual outing we had alone as “boyfriend and girlfriend” which was to the hospital haha. Jared had sprained his finger while wrestling and he needed a ride to get x-rays. We were there for HOURS and I remember the doctor holding up the x-ray saying “well at least it’s not your ring finger” as he winked at me and I said “um sir we have only been dating for 3 days, let’s not get carried away.” Guess he knew!

Jared: As Cass said I don’t really remember a first date either because we always spent time together. The night we started officially dating though we were at a bar called Gracies. This was our go-to spot because it was close to res and was an awesome place. We had had quite a few drinks when I asked her to be my girlfriend officially. Was the first time we ever really made an appearance together in front of our friends. The next afternoon when I came down to visit her I could tell she was giving me the eye of “does he remember that he asked me out last night?” She said “so, how you feeling today? Remember most of last night” and I quickly responded “What? That you’re my girlfriend?

Romantic couples photoSnow engagement picturesWHEN THEY KNEW:
Cassandra: I had a fairly instant attraction to Jared, when I first saw him in a gym full of thousands of college students at our res orientation. I turned to my best friend and said “I call dibs on that guy” honestly never thinking I would see him again, true story. He then knocked on our res door the next night asking if we wanted to go to a party and we discovered he lived just a few doors down the hall. I instantly knew I was in trouble. The moment I knew I had fallen though, would be when he played Wonderwall for me on his guitar after I had said it was my favourite song.

Jared: I told Cass about the TV show Scrubs so she started watching it and we would sit and talk about it for hours. Back then we would type to each other on MSN and I would help her find episodes online, then eventually I would go down to her place and watch them with her. We would stay up all night watching them. I soon realized that this wasn’t going to be a short term thing, if I jumped in it was going to be for the long haul.

Winter engagement photography

Written from Cassandra’s point of view.

I feel like I have to start off this story with the fact that I am OBSESSED with the TV show Friends. I have watched the entire series over and over and over again and continue to watch it daily (it is currently on the TV as I type this). I can pretty much recite every episode. In the early stages of our relationship, I told Jared it was a must for him to watch the entire 10 seasons because I A) make Friends references several times a day and B) if he hated Friends it just wasn’t going to work out.

In October 2016, Jared’s sister was getting married in Vegas so we decided to cross California off our bucket list and take a trip there first. The second that I knew we were going there I instantly put “Warner Bros Tour” on our list of must see’s while we were there because they still have the set of Central Perk from Friends and you can actually sit on the famous orange couch. Also on our list was San Diego Zoo and a few others up the coast so we decided to start in San Diego and work our way up, leaving Hollywood near the end.

Black and white engagement photo

We arrived at Warner Bros and as we walked up to the building we realized that there was a metal detector with security that we had to go through first, naturally because there are stars all over the set. Jared, realizing that pockets had to be emptied, instantly said “I forgot my phone in the car!” and ran away. Lucky for him I didn’t catch on, actually thought he forgot his phone, and decided to go in ahead of him to go to the bathroom. Little did I know, he had a ring. I text him to say so and he instantly ran back to sneak the ring through before I came out.

We then had about an hour tour beforehand, seeing all the other sites with the Friends set being last. The whole time I was shaking and anxious because I was beyond excited and nervous to go on the set (like I said, obsessed). Every time I said “I am sooo nervous!” Jared would quickly reply “meee toooo” haha poor guy.

Winter engagement photo in field

We arrived at the building where Central Perk was, both of us shaking. I just remember seeing the walls have pictures of all the Friends characters and could hear “I’ll Be There For You” theme song playing in the distance and I knew we were close. We walked around the corner and there it was! I just stared in awe. We waited in a bit of a line to go up to the couch and finally did. There is a Warner Bros staff member who stands there to take your picture on the couch so we handed her my phone. She took a few different angles of us and as she went to hand back my phone Jared said “Can you actually take one more?”

He got down on one knee, right there on my favourite orange couch that I stare at on the TV screen everyday, and asked me to marry him. All I remember is hearing cheering from the crowd that had developed around us and the theme song still playing in the background. It was perfect. The staff member had obviously realized what was about to happen and actually caught a video of the end of it which I will forever be grateful for. Amazing.


It was by far the most perfect proposal that he could have ever done. He said he wanted Friends to always be a big part of my life because it is so important to me. Now when I watch it every night I get butterflies. Not sure how long that will last, but I hope it does for a while!

Barnstormers Brewery photosBarnstormers Craft Beer engagement photo

Cassandra: I love how positive he is. No matter what the situation or the outcome of a bad situation, Jared can always find something positive about it. I am a really anxious person, always worried about what could go wrong and he keeps me grounded and positive.

Jared: There are lots of things I love about her, I don’t know how to pick just one, but I love how much people love her. She’s such a people person and everyone just always wants to be around her because she’s so fun and personable.

Barnstormers Craft Beer pre-wedding photo

Cassandra: I am so excited to share our special day with family and friends. They mean the world to both of us and I am just so happy to have everyone around. Looking forward to good drinks, many laughs and so many memories to look back on.

Jared: Agreed. Seeing all of our friends and family in one place celebrating together. Also pretty excited to see my beautiful bride.

Intimate couples photo drinking beer




Muskoka Pre-Wedding Winter Engagement Photos
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Muskoka Pre-Wedding Winter Engagement Photos
A winter wonderland engagement session with my new Muskoka friends Cassandra and Jared. Quiet on set!
Vaughn Barry
Vaughn Barry Photography
Vaughn Barry Photography
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Vaughn Barry

Vaughn Barry

Wedding Photographer at Vaughn Barry Photography
Outdoor Muskoka, Barrie, Collingwood and international destination wedding photographer based in Severn, Ontario (lower Muskoka). When I put my camera down you'll find me with my beautiful wife and 2 daughters or behind the bench as a local hockey coach.
Vaughn Barry
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