How did everyone get engaged?

Complete and total surprise. We were on the Celebrity cruise line ship, the Equinox holiday cruise. He asked me during Christmas dinner. A random passenger heard the commotion (I screamed LOL) and took pictures.

Complete surprise! He took me to Christkindlmarket (my favorite Christmas event in Chicago), and at the end of the night he popped the question in front of my favorite skyline ❤️

Semi-surprise. I’d been thinking it was likely, but then I had a stern talking-to with myself not to expect anything and ruin the trip if nothing happened, so when it happened I was completely surprised! 😆


We met as actors at a local Ren faire themed for Scarborough Faire. This May, we did a big family trip to the British Isles to celebrate my parents’ 50th anniversary and did a few side trips on our own. Of course we had to go to the real Scarborough! We were on the castle grounds on an absolutely gorgeous day and had someone take this picture of us. Then we sat down on a bench overlooking the ocean and he proposed. It couldn’t have been more perfect. 😍

I literally thought he did not want to get married. I always wanted to marry him but was happy just living my life with him. He had recently gotten matching Hawaiian outfits on a work trip in Hawaii. We were in Aruba and our resort had a deal for a private picnic on the beach. Our waiter was in on it and had us stand up for a picture, then suggested we each have one by ourselves. I was posing when my now fiance said my name. I turned, saw him kneeling with a ring, and about died! We were so happy! And still are.

The proposal was a total surprise to me. I had no idea that he was even considering marriage. We were on vacation for one of our dating anniversaries, and the hotel we stayed at overlooked a lake. We were sitting on the hotel's porch, watching the sunset, and in that moment, he asked me to marry him.

By the time we got to the Skybridge in Chicago I was pretty sure he was going to propose. We've been planning out married life together before the proposal. I knew it was coming but was double guessing on the day. S/O to my future husband for having a photographer there waiting to take pics.

Semi-Suprise, I kind of knew it was coming but wasn’t sure when. He’s horrible at keeping secrets and we have already been together 13 years so he would make little comments about it. We were on vacation in Destin, FL and he surprised me while doing a sunset photoshoot

We've been together for 8 years at the time and we love to travel. We have always traveled as a family but we decided to go to Aruba for our first couples trip. I always plan our trips and this was no different, when we walked into our hotel on the first day they had a beautiful table setup in the lobby to promote dinners on the beach. He saw it and said oh we should do that we've never done that before, it was a bit expensive and I debated on doing it but I finally gave in. We decided to do it the next day right before sunset. At this moment I still had no idea he had anything planned to propose. The next day we hung out at the beach and pool and it was time to go get ready for dinner. He was in a bit of a rush since he didn't want to miss the sunset, but whatever lol we finally go to the beach and the table was set up with wine and snacks. He insisted that the waiter take pictures of us with the sunset in the background. While taking pictures my hand was on his chest and his heart was racing which I thought was odd( he was nervous) haha but again w.e lol The waiter then told me to do different poses and one was to look out to the sea and when I turned around he was on his knee with the ring in his hand! I was shocked i really didnt expect it but it was so beautiful. There were other people on the beach and they started applauding. It really was a surprise but a lovely one and he was a nervous wreck the whole time haha

Got engaged at my highschool graduation! Right after we walked the stage! I was totally surprised.

I was totally surprised! We have been dating for 2 years when he proposed. Now, we are on our 3rd year.
One day, he and I went on a date to go to see the Christmas lights at the zoo. He asked me to marry him while surrounded by the beautiful lights. In that moment, I teared up. He asked my parents permission to marry me months ago and I didn't know about this. My brother is terrible at keeping secrets but he was able to keep this one haha.

It was a total surprise. We had been together for a year and 5 months, long distance for almost a year. He told me we were going out on a date for my 21st birthday. He took me to a beautiful botanical garden. There was a little island and we went on it to get the view, or so I thought. He has his friend, my friend, and my sister hide the ring there. It was beautiful and I loved every second of it.

It was somewhat a surprise! We both knew we were getting engaged soon because we had plans for a fall 2023 wedding and I just wasn’t sure when the proposal was coming. He had planned for a proposal at a church after Mass with his sister there to take pictures but she was unavailable the weekend he wanted to do it. He actually told me this plan and I said that’s okay just do it when you want and surprise me. Well we still ended up going to the church he had planned for and proposed after Mass the day he originally planned for lol. I was still surprised because I didn’t think he would do it since he told me the whole plan but he still surprised me and did it then. It was more special too since it was only us and a few strangers from church.

Got engaged at the Signature Room at the John Hancock Building during the evening! Definitely knew it was coming because my fiancé NEVER plans anything and wants me to dress up to the extent I did. He ordered an Uber black to the restaurant and left a note for the driver to not confirm the location, but the driver totally didn’t do that. Our table had wine and flowers, and it was super sweet! He wrote on the menu “will you marry me” and it took me forever to find it, so much that he had to kind of point it out. The whole restaurant celebrated when I said yes, and one of the waiters brought dessert with a candle that said congratulations! Towards the end of the night, there were fireworks at Navy Pier-which was a perfect end to the night!

I kinda already knew however, I started to doubt myself that it was gonna happen towards the ending of the day and then boom it happened hahaha so happy to be with him.

Semi-surprise… he did so well trying to hide everything but I am such a snoopy-nosey person and after being together 3 years, and hes randomly wanting to take a vacation to Mexico this January…and before he always said vacations in Mexico were over-rated (I love Mexico), it seemed a bit suspicious so I was skeptical that he was planning this. As we were in Mexico he waiting until the very last night (which he actually had to improvise because his original plan did not feel right to him). His original plan was the propose at a cenote we visited as I adore cenotes, but the one that is on Cozumel… is a pond… its a tiny pond and that didnt feel very romantic to him. So when we got back from that excursion he had the hotel put together a dinner on the beach, just the two of us, no one around, and let me tell you… it was absolutely, utterly MAGICAL. The whole time i was tearing up and asking if this was real… right before dessert he got down on his knee and pulled out such a gorgeous ring that he picked out all by himself 🥹😭❤️ I truly cannot wait to Marry this man.

I never thought someone woukd ever want to marry me. I am a photographer myself and told him I need photographic proof it happened 😂 he was too obvious that it was happening on our 2 year anniversary but I still cried like a baby 😂😂 best day ever

I would not say completely surprised since I did have a gut feeling it was happening on or around Christmas but I was still totally in shock when he got down on one knee this previous Christmas Eve in front of all of our closest loved ones.

He kept it a secret for over a year!! Planned it all out and told me it was just an anniversary date because he asked me on our 3rd year anniversary. My family and kids knew all about it but I didn’t. He asked me at the Butterfly Pavilion it was not our first time there. I love him so much!! 3/25/25 we say we do!!

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Such a perfect, classic solitaire ring - I love it!

View Quoted Comment Thank you !! It was my grandmother’s stone from her wedding ring !