10 Crazy-Cute Holiday Engagement Stories

It's the most wonderful time of year, especially for these readers, whose sweethearts popped the question just in time to add more sparkle to the season. Here, the details behind their good news in their own words.

"I was in my late 20s when I decided to start my own company. Romance was something I no longer had time for. While single friends were going to parties and dating, I was working around the clock to build Shop Hers. Eventually my hard work paid off. My company thrived, but my love life was stalled.

"When Darren came into my life, I was thrilled. The last day of November, Darren insisted we buy an advent calendar. As a Jewish woman, I had no idea what an advent calendar was, but I decided that anything that offered a sweet message and a chocolate once a day was okay by me.

"Every morning our routine was the same: go to the gym, drink coffee, and read the advent calendar. I'd read the little rhyme that promised that Christmas would soon arrive and Darren often took a photo of me on his iPad. It was sweet.

"Christmas Eve morning, Darren excitingly brought the calendar for us to open. I was in the middle of tackling e-mails on the sofa in my pajamas, but I stopped to open the last window marked with the number 24. Nestled inside the little box was not a chocolate but a diamond ring, and instead of a Christmas message were the words, 'Will you marry me?'

"I was shocked and overcome with joy—an engagement via advent calendar. Brilliant!" —Jaclyn Shanfeld, with Darren Boghosian, of Los Angeles, California

"We were vacationing in Sunriver, Oregon, and the whole week before my friends had been saying that they were kind of expecting it. I was hoping for a proposal myself. Anyway, the morning it happened, we were sitting down at breakfast and he asked if there were any ring shops there. I guess my face fell, but I couldn't tell him why I was disappointed.

"A few hours later, we were on this sleigh ride that we'd managed to get even though it wasn't sleigh-riding season yet. He asked the coach driver if there were any places we could stop and take pictures. We stopped at this beautiful shaded spot right next to the Deschutes River. We were posing and taking pictures. In between a couple of them, I turned around and suddenly he was on one knee and pulling out a ring box from his coat pocket.

"It was the sweetest, most surprised moment I'd ever experienced. Of course I said yes to this beautiful, unique ring, but mostly to him, the love of my life and my very best friend. The rest of the day was a thrilling blur as we called family and celebrated by our home school quarterback winning the Heisman and seeing a beautiful meteor shower." —Anastasia Strgar, with Michael Harris, of Eugene, Oregon

"The weekend started by convincing her we were taking a short flight from Seattle, where we live, to Portland, Oregon, for a quick Christmas shopping getaway. We instead boarded a plane to New York City!

"On the morning of the proposal, she had absolutely no clue what was in store. While shopping, I explained that we had dinner reservations at a nice restaurant and that we needed to be ready by 5 p.m. Throughout the day, my nerves were getting the best of me, and I checked in with Sarah Pease from Brilliant Event Planning, as she was at the restaurant setting up everything. She reassured me that everything was a go!

"Once ready, a town car picked Kimberlee and I up at the Times Square Renaissance. A short while later, we arrived at the Riverpark for dinner. We checked our coats and the hostess walked us through the restaurant toward the back banquet room. 

"The doors opened to a table for two looking over the river and skyline. The room was full of candles, Christmas lights, poinsettias, decorations, and a small Christmas tree. I asked Kimberlee if she wanted to have a look at the decorations. We walked over to the tree. I then handed her a large envelope. 

"She opened it to find a custom-made book with both of our names and the date on the front. Inside was a hand-drawn picture of each ornament on the tree in front of her, which I had handpicked to tell the story of 'us.' Below each pictured ornament was a paragraph about how it related to a chapter in our lives.

"With each page turned, she started to tear up. She got to the last page and it was blank. I told her to turn the page, where she saw a drawing of a New York City ornament. The passage simply read, 'New York City, where we got engaged.'

"Kim turned to me to see me down on one knee, ring presented. I then asked Kimberlee, my best friend, if she would spend the rest of her life with me. She started shaking and crying and said yes! I have to admit, I got choked up and was shaking a bit, too, especially when putting her ring on.

"As dinner wrapped up, I still had one more surprise in store for my new fiancée. We jumped into another waiting town car and headed off through Central Park over to Lincoln Center to watch the New York City Ballet perform the Nutcracker. It was the most amazing night and one one we both will never forget." —Ryan Clevenger, with Kimberlee Clevenger, of Marysville, Washington

"Last week, I went to Aspen, Colorado, for what I thought was just a ski trip with my boyfriend. I didn’t understand why he was so excited about this trip. 'It's just skiing,' I thought. Little did I know he had remembered that I had told him I'd love to get engaged in the snow. 

"When we walked into our room at The Little Nell, white lilies and hydrangeas were waiting for me—still, I thought nothing of it. As we settled in, the jet lag hit and I started to feel under the weather, so I decided to take a nap. He woke me up and asked me if I still wanted to go to dinner. When I said no, I saw the disappointment on his face, so I quickly told him that I would go. Still a little dazed from my nap, I got up and started to get ready. I could tell he was nervous, but I had no idea why. That's when I saw something out of the corner of my eye. I saw a picture that I had given him for Valentine's Day two years ago. On top of the picture was the most gorgeous ring I'd ever seen.  

"Now for those of you who do not know me, I can be awkward and this was no exception. For a good three minutes, I couldn't say anything besides, 'What is that?' He was patient; he said, 'It's a ring.' When I asked what it was again, he said, 'It's for you.'  Realizing that it was a ring and it was for me, I then proceeded to say the smartest thing I could think of: 'I'm confused.' He just smiled and said, 'I'm proposing.' That's when it all became real. That's when I realized my dreams were coming true. And that's when December 11 became my favorite date." —Lucinda Samperton, with Matthew Morello, of Maryland

"Dan and I met in a lounge in SoHo—when my hair caught on fire from a poorly placed candle and he put out the flames. We hit it off immediately. The first time Dan met the most of my friends was at my annual cookie party in early December about six weeks after our first date. Every year, I bake a few batches of gingerbread and sugar cookies, make royal frosting in about six colors, gather lots of sprinkles, and invite all my friends over to decorate the cookies and take them home. It was a bit overwhelming for him to meet everyone that way, but he made it through the evening with the approval of all.

"About a year later, we moved in together, just in time for me to throw the cookie party in our new apartment. Dan seemed a little nervous, but I just thought he wanted the first party in our new apartment to go well. He stationed himself in the kitchen, serving drinks and making conversation, but was not partaking in the decorating.

"About halfway through the party, I was at the cookie station chatting about a friend's recent vacation when Dan came up to me with a plate and said, 'Look at the cookie I just decorated.' On the plate was an engagement ring-shaped cookie from a local bakery, Eleni's. In the center he wrote, 'Will you marry me?' with an edible marker. I gasped. My friends got teary. He got down on one knee and pulled out a ring. I said yes. The ring was custom-made based on a design I had showed him a few months earlier.

"Dan had told my best friend the plan two weeks before, so she was ready with her camera to capture the moment. All my other friends were as surprised as I was, though. We opened the Prosecco one friend had fortuitously brought as a hostess gift and the celebration turned into an informal engagement party. I don't think I will ever have a cookie party to top this one, but we'll see what happens in the years we will now have together." —Jessie Schwartz, with Daniel Kwasnik, of New York, New York

"My boyfriend and I were driving to his family's Christmas Eve party, and I was routing the directions since we did not know the location of the party. I told him to take a right at the intersection and he just kept going straight. I told him, 'You're going the wrong way!' Very coolly, he replied, 'Oh man, I'll do a U-turn here.' I was getting frustrated because the app was going to reroute.

"He then pulled over near a little man-made pond, in front of our local arena stadium, which is beautifully decorated with Christmas lights. 'Oh man!' he said. He got down to check the tires and I panicked, thinking something was wrong with the truck. He asked me to get down to help him with the flashlight. I quickly got down and he got my hand and said, 'Melissa, I love you and I wanted to ask you … ' He then pulled a black velvet box from his jacket, 'Will you marry me?'

"Tears of joy immediately ran down my face. I said, 'Of course.' He got my left hand and placed the ring on my shaking, cold finger. I hugged him and kissed him as soon as he got up. He took me by surprise! I never imagined that I was going to have a Christmas proposal.

"It was just me and him. No photo, no video. He told me, 'We'll just have to take mental pictures like that episode from Jim and Pam's wedding in The Office! To me, it was the perfect proposal. Beautiful scenery, in the night full of Christmas lights. I wouldn’t change anything about it." —Melissa Galvan, with Erasmo Jasso Jr., of Laredo, Texas

"On Friday nights during December, Roanoke does 'Dickens of A Christmas' where actors dress up in Victorian costumes to recite lines and sing carols. The streets downtown are closed for activities and they have horse-drawn carriage rides. Little did I know, Brandon had planned to rent out a whole carriage for us to take a private ride during which he was hoping to pop the question. But I had grown up riding horses, and as such, the idea of a short carriage ride around downtown was not terribly exciting to me and I said no. But this was his big plan, so he kept asking and asking to the point where I began to grow a little annoyed that he was pressing the issue so much!

"Defeated, he suggested we leave downtown and head up to the Roanoke Star, a large illuminated star on a mountain top with an overlook above the city. When we arrived at the Star, it was having technical issues and wasn't lit up, so we again turned around to head home. Still intent on making his proposal that night, Brandon suggested we stop off at another overlook near our neighborhood to look at more Christmas lights. When I complained about the cold and said I just wanted to go home, he said, fine, he'd just go up alone! Feeling bad about declining his earlier plan with the carriage ride, I agreed to go with him.

"While we were alone up there in the dark and cold, with the Roanoke Star flickering on and off in the background, he got down on one knee and slipped the ring out from its hiding place in his sock and asked me to marry him. Not quite the holiday festivities proposal he wanted, but this ended up being the perfect proposal to me, all alone at a place special to us." —Esther Ford, with Brandon Foster of Roanoke, Virginia

"One of our favorite Christmas traditions is to choose and cut our Christmas tree at Palmer Christmas Tree Farm in Mt. Bethel, PA. The Saturday after Thanksgiving has been reserved for this tradition for the past several years.

"We walked around aimlessly for about 20 minutes until I ran to a tree that caught my eye. Ray asked me 'Is this the one?' I said yes, he asked again, 'Are you sure?' 'Yes!' He started to cut the tree when I heard him say, 'What is this?' I turned around and there he was on his knee with a box in his hand. When he asked me to marry him, the first thing that came out of my mouth was 'Are you serious?!' The moment was surreal and I could barely comprehend what was going on. I bent down to give him a hug and kiss and said yes. After he placed the beautiful ring on my finger he told me 'Turn around and say hi to Julian.' Our friend Julian, dressed in a disguise, with fake glasses and all, caught the entire engagement with his camera.

"Julian promptly presented us with a bottle of Champagne and we all celebrated before finishing what we came there to do: choose and cut our tree. After dragging our tree to the car, with huge smiles on our faces, we headed to Ray's dad's house where I was greeted with an engagement party with friends and family who were all in on the surprise. Ray's dad decorated the house beautifully for the holiday and his sisters customized our engagement party themed as 'Always & Firever' to commemorate our Frasier Fir Christmas Tree.

"After nearly 9 years together, I shouldn't be surprised, but I still was! He got me, and I am so excited to say yes to forever with him." —Kimberly Egge, with Ray Soroka of Far Hills, New Jersey

"Clayton and I had been dating for a while and I was very much hoping that he would propose, but did not know when it would happen. We have a very special tradition of going to a cabin with friends and family over New Years, and that year he surprised me by inviting all of my best girlfriends to join us.  The cabin is located in the beautiful North Carolina Mountains in a special place called Camp Buc, where he was a camp counselor throughout high school and college. 

"On December 30, we were all preparing dinner together when my soon to be sister-in-law Blair told me that we needed more wine from another cabin, and that she needed help carrying it back to where we were preparing dinner.  I got in the golf cart with her and we drove to pick up the wine, but instead of going to get wine, she stopped in the middle of the woods and said 'I think someone is out there, waiting for you.'

"I looked ahead (it was dark by now), and saw the covered bridge at camp lit up with a thousand tea lights, and Clayton standing in the center with a lantern.  I walked toward him and he gave a beautiful speech about how he was going to be 'the best fiancé, the best husband, and the best father to our children.'  At this point, of course, I knew what was happening and all I could say was 'Are you going to get down on one knee?!'  He said, 'Wait a minute!' Then he got down on one knee, opened a ring box with the most beautiful ring inside, and asked me to marry him. Of course I said yes! My brother and sister-in-law were waiting in some bushes near the bridge to have Champagne with us afterward to celebrate, and all our friends were waiting with dinner prepared when we got back to the cabin. Clayton is the love of my life and I could not have asked for a better story with him." —Grace Bagwell Adams, with Clayton Adams of Athens, Georgia

"It was the first year that both of our families spent Thanksgiving together, which took place at my parent's house. According to Michael, the night before when he spoke to my dad the first words out of my dad's mouth were, 'I already know what you're going to ask me. We've actually all had a running bet on when this would actually happen.' Michael later told me that he chose Thanksgiving because he knew that it would be a total surprise, rather than waiting until Christmas or New Year's Eve, which was our anniversary.

"On Thanksgiving Day after we had all eaten, Michael suggested that 'we go outside and play with the dogs' (his parents brought their dog over to play with our three dogs during lunch). As we walked into the backyard I didn't even notice that both of our families had also followed us outside and were all lined up on the patio with their cameras ready. After a few minutes of nervous conversation from Michael, he took my hands and said that he'd 'been thinking for a long time about how to do this, but then it hit me that you're happiest when you are at home with your family and your dogs, so I knew this would be perfect'… a lot of other words were said but I was so in shock that I don't remember (luckily Michael has them written down somewhere). I spent the rest of the day on Cloud 9, trying to process the idea that I get to marry my best friend!" —Lauren Trunk, with Michael Marshall of Marietta, Georgia 

Find out how to submit your proposal pics and details at marthastewartweddings.com/submit.