Jeannie and Conner

Where to Propose in Charlottetown, PEI, Canada

How We Met

Conner and I met through a mutual friend, around May of 2011. We were both in High School – He was 17 and I had just had my 18th birthday. We were introduced by a friend of both of ours, and we really hit it off. We dated for about a month or so and decided that because I was graduating and he was going to be in school for another year that maybe the timing just wasn’t right. That same summer, we still kept in contact and it was a hard decision, but we still opted to wait and see how things were once he had also finished school. We lost touch for most of that year after that.

Fast forward to a year later or so, we were both working and we got into contact again. We tried again – but for the third time…We just felt like “right person, wrong time” kind of thing. Still, we remained in contact and checked in with each other every now and then.

In 2014, Conner went on the trip of a lifetime. Packed up and moved to Australia for what was to be a year (which only ended up being just under 6 months). While he was still in Australia, nearing the time that he had decided to come back home, we messaged each other and we began talking again…but this time it was different. Something had shifted between the two of us. We immediately made plans to see each other for when he got back home and was settled in.

There was a bit of uncertainty, or reluctance but wanting to give us a real shot at being together. We both felt like maybe this was supposed to be the time now – we had both experienced a lot since our High School days (being now 4 years since). We made it official about a month or so after he had come home from Australia (May 10th of 2015 to be exact). We have been together ever since. We’ve been through different friend groups, lost and gained friends, moved about 5 times, travelled a little bit…but the one thing that has remained constant in the last few years has been, us. I’ll include some photo’s of us throughout the last 2.5 years.

Jeannie's Proposal in Charlottetown, PEI, Canada

Proposal Ideas Charlottetown, PEI, Canada

Engagement Proposal Ideas in Charlottetown, PEI, Canada

Marriage Proposal Ideas in Charlottetown, PEI, Canada

Jeannie and Conner's Engagement in Charlottetown, PEI, Canada

How He Asked

We were headed to Charlottetown, PEI, Canada for a memorial service and tree planting for Conner’s Grandfather. This was a huge family trip on his Fathers side of the family. There were so many of us that went, and many of whom already live there. After two flights (yyc-yyz & yyz-yyg), we had finally arrived. We pile in with our luggage, into a family members vehicle and off we went headed towards the beautiful cottages we were going to stay in. Firstly, we needed to stop at the grocery store and the liquor store so that we could have a big family barbecue and wind down from flights with a few drinks.

Finally, after the long day of airports, flights, and stops, we got to the cottages. They were the cutest, most quaint looking cottages. The group of us (at least 20 of us), had rented out half of them (totaling about 6 cottages) side by side in the U shaped courtyard. We unloaded our luggage and set up our room in the cottage and headed over to one of the main middle ones where everyone else seemed to be gathered. We walked around looking at the grounds and checking things out, in complete awe of how beautiful the area was and how excited we were to finally be there after planning/talking about the trip for almost a year.

Conner said he needed to go back to our cottage “to get us a beer to drink”, leaving me to mingle with everyone else and continue to check out the courtyard area. I sent a text message to my parents to let them know we had arrived safely and also sent a few of the photos I had taken of where we were staying. Then Conner came back over to where I was sitting at a picnic table out front of the cottage everyone was at, beers in hand.

The sun was perfectly setting, in a picturesque type view among the trees that surrounded. We sat down at the picnic table to relax and take everything all in. Now, at this point I did not have an inkling that he was going to propose at all. So had I known at all then, I would have noticed that everyone was sort of leaving us alone and kind of hanging out on the deck/porch and watching us…

Conner put his arm around me, zipped up my sweater zipper, kissed me on the forehead and then he looked off into the sunset. I thought he looked nervous which for him, is rare. Before I could say anything, he said “Aren’t you happy that we’re finally here?” I replied “Yeah, this place is beautiful. I’m so excited to be here and for this trip!” I saw him smiling.

He tthen turned and looked at me and said “Babe, you know that I love you with all of my heart right?” To which i responded “well yes, of course. I love you too!” then he grabbed my hands and held them and began talking in a more serious but loving tone. “Well, I’ve been doing some thinking, for a while now. I love you, you are the sweetest woman I know, and you have a kind heart. We have been together for two years now and we’ve known eachother for a few years before that even. You’re the only woman I can see myself being with for the rest of my life. I love you with all of my heart, and so I have a question for you”. As you can imagine, I’m welling up with tears, completely surpised, shocked, ecstatic all in one. So, half sobbing i replied “yes?” and he reached into his jeans pocket (me crying more and starting to shake), and he opened up this ring box towards me and said “Jeannie, will you marry me?”.

Looking back I laugh at my response which shows how well he surpised me, because my response was “Are you serious? Like, really? Is this a joke or real?” (crying even more – keep in mind i’m smiling like a happy little lamb underneath all these cries). Conner wiped my tears with his hands, looked me in my eyes and said “No, this is not a joke, this is for real. Of course I want to marry you”.

So I hugged him and whispered “Ok, yes, yes please”. He laughed and took the ring out of the box, and put it on my finger. At that point I hear cheering and a very loud “SHE SAID YES!!!” (Conner’s sister’s voice) coming from the porch direction where everybody else was. I then could hear Conner’s Grandmother holler “POP THE CHAMPAGNE, SHE SAID YES!” And they really did immediately pop some actual champagne for us and everybody else. We hugged a few more times, and shared a few kisses too, and then decided to then call my parents and tell them the exciting news. So, I called them up and it turns out that not only had they already known about this proposal, but he had asked for my Father and Mother’s permission months before. They were thrilled.

We went back up to the deck and headed into the cottage with everyone else (at this point more and more family members/family friends were showing up – they almost all knew). After many hugs and congratulations, I found that pretty well everyone knew this was coming except for me…well, I mean I had hoped for it but I didn’t know it was going to happen at this point int time on this trip let alone. I was shaky and giddy and of course the “When’s the wedding, have you set a date yet?” jokes came in a few times.

Overall, It was one of the best moments in my life thus far and I would not change a thing about it. The sneaky man had the ring hidden for a few months prior to this trip in our apartment too. I do kind of wish that we had photo’s of it all, but I really truly believe that it was better in the moment. For the rest of the trip we only took a few photo’s as well, and I think that is because we just wanted to enjoy this time together on the island where we got engaged. The remainder of the two week trip was amazing as well. This was one trip I will always cherish. We are now 5 months until wedding day and we are over-the-moon about it still. I will include some photo’s from the trip and one from when we were back home as a newly engaged couple.