Our Favorite Funniest Engagement Stories

comments: 55

Guys! I'm sorry I've been gone so long. You would not believe the chaos here this week. Carpet is in, bird kits are out, house is in shambles, and Remy (a.k.a Mumsie) arrives in five minutes to be dogsat for five days, so this will be quick. But here are our favorite funny engagement stories!  It was sooooooooo hard to pick -- there were so many great stories -- but in the end, after we each had read them all separately and then told each other the ones that made us laugh out loud, for whatever reason (sometimes it's the story, sometimes it's the telling, what can I say?), these were our ten faves. (But honestly, thank you for sharing them -- we really loved them all.) Be warned, some of them are a little bawdy! But without further ado, and in the order they were received, here they are:

1. You Just Can't Make This Stuff Up

3/25/05 was good friday and my family (in NY) goes to this rustic buckwheat pancake house every good friday. it's my favorite tradition. ben flew from CO to NY to surprise me, and stayed with a family friend who is disabled. I was really confused because we got priority seating because of our disabled friend. We've always had to wait 1-3 hours for pancakes and never got priority seating. I thought my dad was cheating (because he often does)and I yelled at him as we were being seated. Then my dad handed me 6 plastic easter eggs. While drinking my maple milkshake (and later choking on it), each egg included a note from Ben which got progressively sweeter. The last egg said to turn around for my real easter gift and he was there! hiding in the kitchen! I didn't know he was proposing, and bent down at his level when he got on his knee, giving him the wrong hand. Everyone cheered and we got heart-shaped pancakes and they remember us and have a picture hanging in the restaurant- it was a great day."

Posted by: Emily | March 16, 2009 at 01:58 PM


2. Hotel robe: $60. Puppy shampoo: $4. This kind of romance: Priceless.

Ok - our engagement story was a night and morning we will never forget.
I refer to these memories as "doodle-gate"
Ben took me to a beautiful chalet in the hills and we had a romantic meal. It rained, we had a fire, chocolates, wine - the works.
Ben and I got into the one size fits all white fluffy robes. I soon discovered that one size doesn't fit all, as when I opened my eyes (after my hubby told me to close them) there was my soon to be hubby on one knee with his weener hanging out of his gaping robe. Of course he did not know this and went into a beautiful, heartfelt will you marry me monologue and I was trying not to laugh, or stare.
The next morning we went home to see our new puppy. Hank had been with us for exactly 4 weeks and this was his first night unattended.
Ben went out into the yard and I was on the phone calling my Mum to tell her our news. Mum wanted to speak to Ben, so I handed him the telephone and Hank ran in to greet me.
I was patting Hank and giving him kisses and while I was doing this I was saying to Ben "why is he all wet?" and Ben was waving madly at me from the phone.
When he finally hung up, he said "I pee'd on the dog. I was out in the bush and the dog ran between my legs".....
You can't buy this sort of romance.

Posted by: Toni Brockliss | March 16, 2009 at 04:22 PM


3. Andy Said, "Yeah, Pick the 'Popcorn Bob' One. I Don't Know Why, I Just Like It."

My (now) husband and I had been dating for a while and I knew we were going to get engaged because we had looked at rings together. I'd actually already been planning the wedding, but he hadn't actually asked.

So you would think that there is no way that I would be surprised, right? Ha! You just don't know how slow I am.

I was living in a house with my little sister, on the other side of a tri-plex (yes TRI-plex, that's a whole other story) from my honey and his roomie. We spent all summer, the four of us, working in our garden like some tiny commune. I worked at a preschool during the day and when I came home I'd make dinner for everyone while they all hoed and pulled weeds and hung the laundry out (what can I say, we were in college) in the backyard.

I'd had a particularly bad day at the preschool and my sweet honey took me to a place we'd been on one of our first dates, but it was closed. I still have no idea why they were closed on a Thursday night. It should have been my first clue, because he was terribly disappointed. Instead we went to another restaurant, that was very nice and then we came home. I asked him to let me go change clothes and then I would meet him to go for a walk. While I was in my room changing, Josh went out into the backyard and lit about fifty tea lights all around the backyard and into the garden, leading to our scarecrow, Popcorn Bob. There was a reason why we named him that, but I can't remember what it was now.

Just as he finished lighting all these candles his old roommate drove up and flattened a few. He didn't stay long because he caught on pretty quickly as to what was going on.

Josh left a note outside my bedroom door (like I said, I hadn't caught on so I was taking my time) and called me after I didn't come out for a while. I read the note and it was a poem about all the weird names of people we knew and it instructed me to come outside to our scarecrow (the aforementioned Popcorn Bob). I came outside (still clueless) and found all the candles and my sweetie standing in the middle of the garden next to the suspended overalls. He gave me another note telling me to look in the pocket of the Bob's overalls and I did. And I dropped the ring in the dirt. In the dark. After some scrambling we found the ring and Josh proposed.

Posted by: Chara Watson | March 16, 2009 at 09:23 PM


4. "I Do," but First a Little Profanity

Ok, so this is the story of my little sister's engagement (just happened on New Years Day!)

My sister and her boyfriend had been dating for about 7 years. He had joked around with her numerous times about getting engaged without ever proposing (example, a few months back her boyfriend's brother was planning on popping the question to his girlfriend. The ring was at their parent's house. My sister and her boyfriend were over there visiting when he opens up a drawer and throws a ring box at her. She opens it up and gasps and says "what's this?" he says "well, what do you think it is?" she's about to ask if it's an engagement ring for her when he tells her that it's his brother's ring! How mean!)

Anyways, New Years Day - we have a family tradition of eating Chinese food and getting excited about our fortunes. My sister's boyfriend gets up to help grab the fortune cookies and passes them out to everyone. Everyone is cracking into their cookies when my sister says "oh, look I've got two fortunes" then she yells (in front of our parents, aunts, uncles, cousins and grandpa) "#&%* Off!"

It turns out her fortune cookie said "Will you marry me?" and she thought her boyfriend was playing a trick on her!

Lo and behold, he wasn't this time, she turned next to her and he was on one knee!

The only regret of the night was that my brother wasn't able to get to the video camera fast enough to witness the cursing!

Posted by: Michelle | March 16, 2009 at 10:07 PM


5. Note to Self: Check Calendar First

We got engaged after my exams at the end of second year and phoned home all excited and giddy to let my mother know our good news. She had a strange reaction - was not pleased at all. She told me to stop with the joking around and that it was not funny. I insisted we were serious and she said,"So this is not an April Fools joke?" and I thought,"OMG is it April 1st ?" and then I turned to my boyfriend and said, "April Fools"? feeling suddenly sick and that maybe he was pulling a joke on me. He mistook my reaction and said April Fools!!!" looking stricken, thinking I was telling him that my acceptance had been a joke. But then I really thought he was pulling a very unfunny joke on me. Both of us thought the other was fooling around. It was terribly confusing, sort of like an Abbott and Costello routine. We sorted it out eventually, but everyone we told also thought it was a joke. No one believed us...Do not get engaged or tell people about it on April 1st. But most people know that don't they!!!

Posted by: Karen | March 16, 2009 at 10:17 PM


6. When You Forget There's Been No Proposal . . .

My husband and I had been together for a few years, had been cohabitating for 6 months or so. We had talked a little bit about staying together forever. I apparently used to bug him just a little bit "when are you going to ask me to marry you?" etc. In fact, Christmas 2004 I had said out loud, while in the presence of his entire family "It's odd that I married someone who isn't a miner, given my family history of doing that" and he said "Uh, Donna, we're not married." Right. . . .

(Editor's note: They did get married later, but I just busted out laughing when I read this paragraph :-)

Posted by: Donna | March 17, 2009 at 05:07 AM


7. When the Crazy Old Drunk Lady's Husband Is Just Too Slow . . .

Matt proposed to me on top of the Peabody Hotel in Memphis after a gorgeous dinner. It was a starlit night, ducks were quacking, and Matt got down on one knee.

I could tell that he'd worked so hard, saving money for the ring (we were poor, slightly insane 20 year old college students) and picking the most romantic engagement setting he could find.

He gazed into my eyes, popped open the ring box and then... before he could say anything an older woman reaking of beer came out of no where, grabbed his shoulder and leaned into my face.

"Is he PROPOSING???!!!!"

Everyone on the roof stopped what they were doing and stared at us and the elderly drunk woman with blue hair.

I stood there with my mouth gaping and Matt (bless his heart) said softly, "Well ma'am, I'm trying to."

It was so awful it was funny. Drunk lady's husband came running across the roof, apologized profusely and led her away as she yelled, "They're gonna get marrrriiieeeed," to anyone that would listen.

Matt shrugged, looked at me and said, "Well?" I said, "Ok." And that's our engagement story.

Posted by: Liz | March 17, 2009 at 06:26 AM


8. Napping, but With One Ear Open

Larry and I had been together for nearly a year. One afternoon I was "napping" next to him. I heard him ask if I was sleeping, but just didn't feel like talking so I did not answer. I was too exhausted. Next thing I hear him say is "Marsha, will you marry me?" "What?" I immediately said as I was sitting up. He said he was just practicing. Who practices that with the person right there? Of course who "fake sleeps" too? Needless to say that was my one shot at a proposal and I took it. We have been happily married 12+ years and are the proud parents to 5 wonderful kids.

Posted by: Marsha Roberts | March 17, 2009 at 11:16 AM


9. Aw, thanks, Dad -- but what are you talking about?

My engagement story: my long-time, cohabiting boyfriend decided to propose to me, but thought it would be polite and old-fashioned to tell my parents about it first. My dad, being a pretty modern guy, naturally thought that Michael was telling them AFTER the fact, since why on earth would he tell them that he was GOING to propose before asking me? [I'd have to insert a long paragraph here about how soft-spoken and, well, shy my spouse is to make it more clear how this misunderstanding could have happened]. Anyway, I was at home, wondering where on earth Michael was, when my dad calls and says, "Oh, my little baby, we are so happy for you!" Then I hear my mom in the background saying, "JAY! Hang up right now!" (apparently she hadn't misunderstood). There was some rustling around, and then "click." It didn't take me long to figure out what was going on, and as soon as Michael got home I told him about it--he ended up "proposing" with a red face, and now almost ten years later I love to tease him about how romantic it was when my dad proposed to me!

Posted by: Katie | March 17, 2009 at 11:23 AM


10. What Happens If You Wait Too Long

Okay, here goes. My boyfriend and I came to the mutual conclusion that we wanted to marry each other at about the same time. It was about Christmas, 2006. We went ring shopping together, which (admittedly) did take some of the element of surprise out of things, and picked my ring out sometime in early January.

What ensued was three months, that's right, THREE MONTHS of torture! I knew he'd picked up the ring, I knew he had it, I just didn't know WHEN he was going to finally propose! I was dying to share our good news with our family and friends! During this time, we would have a game we played:

Me: Sure would be nice to be engaged...
Him: Oh yeah? What makes you think I'd want to marry you?
Me: Well, we picked out the ring...
Him: Mmmm, yes. About that ring. Where do you think I could've hidden it? It could be anywhere... I could be looking at it RIGHT now!
Me: Aarrrggghhhh!

It was March before he finally got around to things. On a nice, sunny Saturday, completely out of the blue he made a suggestion to head up to a state park where we'd gone on our first date. Patrick is not the type of guy who typically suggests plans for a day, so my suspicions were roused.

I said, "That sounds like a great idea. Actually, I'd been thinking about how nice it would be to go to [insert name of state park here] and get engaged."

He immediately deflated, and I realized, shoot, he's actually planning on proposing.

And of course, that's exactly what he did.

Posted by: Kristina | March 17, 2009 at 02:57 PM


Yay, I got picked! Woot woot! Now I have to go find Patrick and tell him. I'm sure he'll be just thrilled.

Oh, Lordy. I am laughing so hard I can barely breathe.

I'm sitting alone in this darn apartment laughing to myself like a crazy woman. I LOVE the 4th and 5th stories! too funny.

These are great! But, truly, the funniest of stories happen after the I do and you are trying to make it all work. ~Kelly

unDeniably Domestic

omg number 8 is my fav!!!!!

Ha ha ha ha ha! No wonder you had a hard time choosing!

I can relate to number 10, it was 6 months after collecting the ring before my husband proposed - but was very lovely when he did.

These are great! Now I don't feel like my engagement was so...not normal. :)

Mary Ann/Ca says: March 25, 2009 at 05:38 PM

Perfect choices, my DH told my teenage daughter we were getting married so he could surprise her with the fact we bought a house...duh!He thought the house would be more exciting then a wedding.

haha these are some good ones..

These are fabulous. #8 especially!

love these!!! what great memories. thank you all for sharing them. :)

You know, I coulda told mine funnier if I'd known there was going to be a contest! Congrats to all (I got Alicia's book for Christmas)!

I'm in love with Popcorn Bob, and like Andy, I have no idea why.

Great choices! I'm having a hard time picking my favorite. But they all made me laugh!

Thank you all for sharing your stories and thanks Alicia for the idea of posting them!

Esther Sunday says: March 25, 2009 at 06:49 PM

These were fabulous! Just great! I really busted a gut on the "practice" one! Wishing lots of love and happiness to all the love birds! Love, Esther

OMG I think I peed myself a little bit over the 'practice proposal/pretend sleep' story. That has to be the funnies thing ever and I totally woke up hubs w/ my weazing can't catch my breath laughing! Thanks for that!

Great stories! I about fell off my chair laughing at the one with the weener hanging out of the bathrobe and the wet dog! in fact I laughed right out loud and then had to read it to my husband and son (hes 20) any ways.. they both just looked at me and then at each other and then my son told my husband that I shouldnt be allowed on the internet! haha! thanks for the laughs!

Way past time, and not funny at all, but my husband propsed to me at Kennedy School two years ago. He made a movie with pictures of us and a great song and had them play it. The pretense was going out for his siters birthday. i had no idea. They said it was the first time anyone had ever done that. It was so sweet!

These are HILARIOUS! So glad we all got to share in the fun!

Fun! No wonder you had a hard time deciding!

I am so glad you liked my story. All of the stories were so heartwarming and FUNNY

Story No. 8 will have me chuckling for a good while :-)Thanks to all those who shared their stories!

Hahahahah! The April fool's on is my FAVORITE!!!

My favorite is number 8 - Napping, but With One Ear Open. Reading all this little stories made me feel happy – love is the best!

Verify your Comment

Previewing your Comment

This is only a preview. Your comment has not yet been posted.

Your comment could not be posted. Error type:
Your comment has been posted. Post another comment

The letters and numbers you entered did not match the image. Please try again.

As a final step before posting your comment, enter the letters and numbers you see in the image below. This prevents automated programs from posting comments.

Having trouble reading this image? View an alternate.


post a comment

About Alicia Paulson


My name is Alicia Paulson
and I love to make things. I live with my husband and daughter in Portland, Oregon, and design sewing, embroidery, knitting, and crochet patterns. See more about me at aliciapaulson.com




Since August of 2011 I've been using a Canon EOS 60D with an EF 18-200mm kit lens and an EF 100mm f/2.8 Macro lens.