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Funny Engagement Stories

Wendi J.

John and I were on vacation in St. Lucia in June of 2008. I had planned to go down to the spa for a relaxing evening. It was about an hour before my appointment, and he kept telling me to leave. "Go now, they'll take you early," he kept saying. So, I left. I got to the spa, and they did take me righ ... [read more]

Tosha D.

My boyfriend Dwayne and I had planned a couple of months before that we were going to see each other the weekend of June 20th. At the time, I lived in Georgia while he lived in Ohio. What we didn't plan was the extra weekend (Memorial Day) that Dwayne would spend in Atlanta. We had a great weekend a ... [read more]

Stephanie B.

Having done nothing by the book in our relationship thus far, it came as no shock that our marriage proposal was unique. My fiancé popped the question during our first year of college: it was about eight months into our relationship and around 2 am in the morning when I was walking him to his ... [read more]

Stephanie A.

One day in January, my boyfriend David came down to Georgia for a visit. I arrived home from work, and he wanted to go out and run some errands. I went with him, and we first stopped by the Apple Store to repair his IPod. While we were waiting, Beyonce's "Single Ladies " music video played on a scre ... [read more]

Sherin T.

My engagement story is not as elaborate as those of my friends, but it was perfect in all of its simplicity. The Brooklyn Bridge has been a key monument in so many of our dating adventures: it was the site of my first meeting with his mom, the bridge we walked across every time we had guests come to ... [read more]

Serena P.

My now-fiancé and I had been dating for three years when he proposed. Last July, I was at a co-worker's baby shower in San Diego, and she told me to call my fiancé and ask him to stop by for some food. Well, I called him and he said he was working, but he wanted to meet up at my place ... [read more]

Sarah W.

On the Saturday before Christmas, my boyfriend Michael asked me to go to Philadelphia with him, and I agreed. Of course, the night before we were supposed to go, there was the biggest snow storm of the season, and I put up quite a fight about going the next day because I was not so sure that his car ... [read more]

Sarah S.

Chad and I started dating in July of 2005. When I recently returned home from a two week vacation with my grandparents, I pulled up to my front steps to find him waiting on my porch with a black and white kitten. He asked, "Will you be my girlfriend?" It was cute, as was the little kitten we named O ... [read more]

Sarah N.

My fiancé was a best man at our friend's wedding. We had spent the entire day having a blast with the 400 guests that were present. During the supper, I was seated with some of the ushers, while he was up front next to the groom. The speeches began and my fiancé followed the maid-of-ho ... [read more]

Sabina C.

It was the day of the fourth anniversary since our first date. I wasn't feeling well so I sat in bed until around noon. My boyfriend had left for work. We had made plans to go ice skating in Atlanta's Centennial Park, and it was getting late. We left for the park at around 7:45 pm. Before that, I ha ... [read more]

Rachel S.

My fiancé and I both love to be outdoors. His family has a camp on a beautiful lake in the Northeast Kingdom of Vermont. For my 30th birthday, my fiancé took me to camp for a week, but it rained the entire time. We had planned to boat, hike and swim, but we couldn't do any of it. Still ... [read more]

Pamela S.

My fiancé Christopher and I had been discussing getting engaged for the past year. He would always say things like "Oh let's wait because we won't be able to get married for a few years anyway " or "You know I love you, why do you need a ring? "We were living with his mother at the time, and ... [read more]

Nevia R.

One Friday, James and I were house-sitting for his parents, and we had just finished a delicious dinner that he prepared for our monthly "date night." While he took the dog out, I got my pajamas on, and then we went to watch a movie. As I was changing in the downstairs bathroom, James came frantical ... [read more]

Mira S.

Mike asked to take me out to dinner to celebrate Christmas together because we were going to be spending the holidays apart with our respective families. He bought tickets to the Walt Disney Concert Hall for the Organ Spectacular on the same night. We've always enjoyed attending concerts at this hal ... [read more]

Melanie C.

My boyfriend Chris and I were taking our dog to the beach for a swim, like we usually do. I was wondering why my boyfriend was bringing his snorkel, but I didn't put it together. When we got to the beach, I started throwing the ball for our dog, Bailey. I did this a few times and noticed that Chris ... [read more]

Megan N.

One weekend, my fiancé was in Cleveland for a visit. We had a nice and relaxing day together before heading out for dinner. He had made reservations at a locally owned, super-posh restaurant that I had wanted to go to for a long time. Right before we left, he said, "Hey, we should go see Enza ... [read more]

Megan J.

Well Rhett asked me what I wanted for Christmas, I said a ring. A few days passed and he asked me again, and I told him I wouldn't mind a St. Louis Cardinals jersey. He is a really big Cardinals fan, and I thought it would be cute if I could wear a St. Louis Cardinals jersey with him when we watched ... [read more]

Lindsey L.

Our engagement involved a haunted hotel, an ambulance, the ER, fourteen dozen roses, runny mascara, some cunning schemes on my fiancé Chris's part and one sparkly bit of happiness. After Chris graduated from law school in May, we drove from Minnesota to Colorado for a brief vacation before cl ... [read more]

Laura M.

Paul and I had been dating for about two-and-half years when we started to look at engagement rings. By the time our third anniversary in December rolled around, I had started to lose hope that Paul would propose. I figured that because so much time had passed since we last looked at rings and becau ... [read more]

Laura A.

Each summer, Chris and I travel up to the very northern tip of Maine, where his late father's family lives. This year, Chris set up the trip so that we flew into Portland and then rented a car to drive the further five hours north. Our only goal was to stop at Mt. Katahdin, the site of a meaningful ... [read more]

Kelly L.

Jerry and I had been together for a little over a year. We had already been through a lot and had been talking about getting married off and on for a little while. I was on my way home from work one night, and I just felt like it was the right time to ask! I bought a Reese's Cup from the snack place ... [read more]

Katy H.

After dating for a year and a half, Ross proposed to me right before Christmas. He took me out to dinner at our favorite restaurant and then when we got home, I tried to change into my pajamas to go to bed. But first, he made me wait on the couch so he could go get the cat we had adopted together to ... [read more]

Katie M.

My boyfriend Jake had an engagement ring custom-made at a local eclectic jewelry store in town, which is one of my favorite places to window-shop. He purchased it sometime in March and couldn't bear to keep it a secret. He immediately spilled the beans when he got home and just had to show me the ri ... [read more]

Kathryn H.

Mike and I had been together for over three years, but I had known that I wanted to marry him after half a month. Soon, we moved in together, and I was just waiting for him to propose. One day, he asked me for my ring size, and I thought he was being very obvious. When he saw how cocky I was that I ... [read more]

Jocelyn W.

My boyfriend and I were on vacation in Key Largo. On our first day there, we decided to relax and hang out on the resort grounds. We had some lunch at the outside cabana bar, drank a few lounge chair drinks and jumped in and out of the water since it was so hot. At one point, a baby manatee came up ... [read more]

Jenny D.

It was a normal Saturday, and it was raining. I just finished teaching Saturday school, and headed to Vinnie's house. We were in the middle of renovating his basement, so I was dressed in sweats and a regular tee. When I got to his house, I noticed that he was wearing the same shirt that he wore on ... [read more]

Jennifer B.

My fiancé decided to propose to me this past Christmas to give me something happy to think about during the holiday. My dad had passed away in June, and it would be my first Christmas without him. My fiancé knew I was having a really rough time. So, on Christmas morning, he saved the r ... [read more]

Jason C.

In November, I wrecked my quad and broke my foot and found out that I needed surgery. I knew recovering would be a huge challenge, but my fiancée Lyndsie had been there for me every step of the way. When Lyndsie left for a mission trip, I realized how much I needed her there not just to help ... [read more]

Erica Z.

My wedding proposal wasn't romantic, and it would leave my friends weak in the knees from laughter, but I wouldn't have had it any other way. My fiancé Chuck and I had gone to a jeweler in Kankakee to have a battery replaced in his watch. While at the store, we were just looking around at the ... [read more]

Emily S.

One day, my fiancé mentioned that we should go out to a nice dinner. I thought he was being sweet, but I didn't think he would propose. As we arrived at the restaurant, we discovered that it actually turned into a club after 9 pm. My fiancé was furious, and we began to brainstorm where ... [read more]

Elizabeth P.

My fiancé Michael and I met after I returned from an eight-month internship with Walt Disney World Resorts, and I was constantly trying to express to him how much my experience had meant. We took our first trip to Orlando together when I got back from studying abroad in Japan a year and a hal ... [read more]

Elizabeth A.

It was our five- year anniversary, and we decided last minute to take a Barbados vacation. We had nothing planned but to enjoy the beaches and sun! After a beautiful cliff top dinner of fresh seafood and fabulous wine, we walked down to the beach for a stroll. Just as I took a step on the beach, a g ... [read more]

Danielle M.

My boyfriend and I knew about six months into dating that we were going to spend the rest of our lives together. A year and a half later, I was wondering when we were finally going to make it official. One Saturday in October, we decided to drive upstate to take in the fresh air and foliage. Our des ... [read more]

Courtney D.

My wedding proposals (yes, I had two) were thankfully low-key, private and completely unplanned. Plus, both proposals were serious, coming from a guy that usually avoids taking anything seriously. The first proposal happened when my boyfriend and I were relaxing at his apartment on one hot Saturday ... [read more]

Coleman W.

Since the early summer of 2008, I had known that I wanted to propose to Jessica. I had gone shopping for engagement rings several times but had never quite found exactly what I wanted. This past October, my mom came to visit in New York for a few days. Since I needed a female opinion, I asked my mom ... [read more]

Christine P.

Last February, my fiancé Jamie and I were taking a trip to Cancun, Mexico. The flight went smoothly except for the fact that security checked my unwieldy duffle bag on wheels at every checkpoint. They never checked Jaime's because he always travels lightly and carried a small satchel. When we ... [read more]

Charlotte B.

On Christmas morning, the snow had fallen in small flurries, and my mom lit the fire and said that Santa had delivered all of his goodies. I was just tidying away Santa's mess, the soot from the fireplace and half-eaten carrots, when my boyfriend decided it would be nice to pull the crackers (Christ ... [read more]

Carrie H.

Last December my boyfriend Mark planned a trip to Hawaii for us as a birthday present for me. To make the time more memorable, we arranged a dolphin interaction at the Sea Life Park for the middle of the week. I emailed my friend, Stacy, ahead of time because she is a dolphin trainer there. Fitting, ... [read more]

Ashley D.

The weekend began with a long-awaited trip to New York City at Christmas. Christmas is my absolute favorite holiday and New York is my favorite city, so my fiancé knew it would be the perfect time and place. He got us a room in the middle of Times Square with a phenomenal view. He also hired ... [read more]

April F.

My fiancé and I had been together for five years when he finally popped the question. We went to his grandma's house for our annual Christmas dinner. His entire family was gathered around for a prayer when his grandma proceeded to say how grateful she was for the family and how someone had an ... [read more]

Annie J.

Last August, I was scheduled to work in Long Island for the whole week, so I was staying at my parents' house instead of my regular apartment in New Jersey. I had Wednesday off and decided I would go shopping with my mom and younger sister during the day. In the morning, I got a text from Gary sayin ... [read more]

Andrea A.

On the day of the first snowstorm in the tri-state area, Luke and I had plans to be in NYC to see the Radio City Christmas Show. We took the train down and hurried over so we wouldn't be late! When we got there, I was amazed to see such a festive place. There were sparkles and lights all over. The s ... [read more]

Amanda H.

It all started out when my two best friends (who are also a couple) invited me and my boyfriend to celebrate their birthdays on a cruise to Cozumel, Mexico in June. On June 5th, we hopped aboard the "Enchantment of the Seas " to start an adventure that would remain unforgettable. On the second night ... [read more]

Allison M.

My fiancé and I live about two hours away from one another, so we decided we needed a little getaway for ourselves last spring. We were both trying to save up money, so we opted for going to visit his great aunt in Arizona and staying with her for free. We also have friends in the same area, ... [read more]

Allison F.

One wintry day in December, I joined my friends at a fun festival they hosted, called "The First Annual Mistletoe Gala. " I met my soon-to-be fiancé Matt there, among countless other revelers. We sat at the same table, chatting the entire evening away. We both had a wonderful time, sharing jo ... [read more]

Alexis S.

A month before my boyfriend Taylor proposed, we had bought a house and moved in. Taylor secretly invited our closest friends over to the house and surprised me when they showed up. I had a feeling he was going to propose, but as the night got later and the drinks got lower, there was still no propos ... [read more]

Adrienne C.

My fiancé and I had met at church, and our pastors were very happy about our relationship. My fiancé took me to his favorite pancake house one day and planned on proposing but felt that the mood wasn't right. As we were leaving, we ran into two members of our church. One of the women m ... [read more]
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