Hilariously Awkward Marriage Proposals

Marriage is a big step for many couples, and deciding to tie the knot is such a big deal that planning a proposal can involve nearly as much effort as planning a wedding. But not every proposal ends up being as romantic as you think it might in your head.

Jumbo Fumble

Sometimes, even the best laid plans fall victim to hapless errors. Take this one sports fan forget to check that her sign was right side up before her surprise appearance on the jumbotron.


Moogical Marriage

Some are dog lovers, some cat lovers, and then there are cow lovers. This country bumpkin thought it wise or even romantic to propose marriage by writing it on the family cow. We must admit, this one just seems outright weird, but hey, if you love milk, or just love your pet then some may take it as creative expression. At the very least, we hope the cow got a bath that night, but hopefully these farmers got the happily ever after they were looking for.


The Doctor’s Remedies

This one doctor had the perfect remedy for his girlfriend’s illness. An engagement ring, packed into a prescription bottle, and labeled with “Will you marry me?” Given that she’s wearing the ring, we can guess that the doctor knew just the thing to cure her future, and that she was a dutiful and compliant patient. Hopefully, the doctors prescribing skills continue to remain on point, and he can effectively keep their marriage together for the rest of their lives.


Love Is A Rollercoaster

This adrenaline lover had a really cute idea to propose to his girlfriend: have his friends sneak signs onto the rollercoaster with them, and time their reveal perfectly with the rollercoaster camera. Proposals like this generally involve the unsuspecting girl finding the photo, only to turn around and see her man on one knee, holding a ring. This guy probably didn’t expect his girl to look so completely terrified when the picture was taken, however. Now that’s something to show the kids.


Google Marriage

In 2013, one man really wanted to take advantage of today’s technological advances by preserving his proposal for all time on the internet. That is until Google takes new Google maps photos. But in the meantime, when he heard the Google camera would be driving through his neighborhood, he was careful to clear his schedule and show up with a large, homemade sign that read “Proposal 2.0: Marry me Leslie”. We hope Leslie took this grand gesture in stride, otherwise this is just a little over the top.


Frosty Fiancée

This guy maybe should have thought twice before hiding a ring in a Wendy’s Frosty. First of all, if the straw is big enough for a ring to get sucked up it’s obviously a choking hazard, and second of all, if your girl loves Frostys enough that you think chucking the ring inside is a good way to go, you also shouldn’t be too surprised when she refuses to back down from a Frosty slurping contest. Next time just hang the ring on the straw.


Not Playing Chicken

Shineka must really love chicken if her prospective fiancé thought it was a cute idea to ask her to marry him by getting the local Church’s Chicken to post it on their sign. We can only imagine that this pair has spent many a date night chowing down on chicken together. Maybe it was even the site of their first date? Hopefully, the sign included a ride for Shineka to the proper Church’s location, and ended with her man down on one knee.


Whale You Marry Me?

This is sort of what we imagine a role reversed Little Mermaid would look like. Ariel jumping into the sea to join her prince, who asked for the help of a dolphin in order to propose marriage. Unless of course the dolphin was proposing itself, and the girl just utterly ignored it in favor of the handsome prince. It’s not the dolphin’s fault it only can only flip its fins. Either way, it’s a pretty creative proposal.


Taco Wedding Bells

About 3 years ago, Taco Bell released a series of hot sauce packets that included several bizarre phrases on them, including one that said “Will you marry me?” One man must have thought it would be a good idea to ask his hot sauce loving girlfriend to marry him with a packet of sauce tucked into the engagement ring. Then again, perhaps the recipient of the ring likes the sauce more than she liked the person who was presenting it.


An Unfortunate Beginning

There’s no better way to show you love someone by pretending to fall off a building, before landing on a crash pad labeled with “Will you marry me?” You’re quite likely to scare your significant other so much that they may say no for fear that other outrageous stunts will forever be their lot in life. Unless of course, they’re looking for a man who shows his undying love by staging a horrific accident to see just how much they care.


Pepsi Marry Me

Well, we sure hope that Steph is a big fan of Pepsi, because this towering Pepsi proposal is really a work of art. Her boyfriend (or the store employees if he doesn’t actually work there) must have spent hours placing the gray Pepsi boxes just so, in order for them to spell out “Steph will you marry me” when you step back and look at the wall. It would be a particularly cute proposal if they were both employees at the same store.


Every Rose Has Its Thorn

Everyone knows that rose petals on a bed is supposed to be one of the most romantic gestures a person could do for another. It wouldn’t be the first or the last time that we saw a bed with “Will you marry me” spelled out in roses on the cover, but this person should have probably checked a dictionary or even their phone’s autocorrect before going with what we imagine was his phonetic spelling of “marry.”


Cheesy Proposal

Ben and Steph must really love Dominos pizza if he convinced their local branch to post his marriage proposal on their parking lot sign. Good thing he specified it to Steph, so unsuspecting customers didn’t head in to the local shop to pick up a pie and an engagement ring. We just hope that Steph isn’t lactose intolerant, otherwise this was a super awkward direction for a proposal to take. Maybe just write it in pepperoni next time.


Everlasting Love

In case you ever worried about the continuing desecration of the institution of marriage, you can make sure it really lasts forever like this guy, so he will never forget that he definitely asked Caroline to marry him. The real question though is did Caroline have to tattoo her answer as well, just so posterity never forgets their undying pledge to one another. And if for some reason it doesn’t work out, we hope this guy is prepared to only date Caroline’s til he finds the one.



Sometimes, we love a food so much, it would seem prudent to just marry it, as marriage is generally taken as a statement of our undying love towards one another. In the case of this couple, we’re unclear as to whether the pizza or the partner is doing the asking, or maybe the proposer thinks that a bribe is necessary. We just hope this pizza proposal wasn’t intended for a New Yorker, because in that case the answer would be a unequivocal “no”.


Popping The Question

It might have been prudent for this guy who hid his girlfriend’s engagement ring with a bunch of balloons to consider adding weights to the bottom of the balloon in question, in the case of a windy day. Alas, he did no such thing and before he could give new meaning to “popping the question” the balloons flew away, and this poor man was engaged in a mad chase to find the balloon hiding the ring. After two hours of chasing, he gave up.


I Can Haz Marriage?

As meme culture continues to proliferate, it’s easy to imagine the next generation will be ever more comfortable proposing to one another via the internet meme. This avant-garde proposal takes its inspiration from the meme’s earliest days, where a photo would be set into a colorful background, before including the classic bold white text. In an ode to “I can haz cheezeburger”, it reads, “Katie I love you so much, I can haz your hand in marriage?”


A Darker Kind Of Proposal

It seems one viewer was so moved by the titillating book and film series 50 Shades of Grey that according to one tweet, he got down on one knee the minute the credits rolled in theatre. Maybe not the best time for that, buddy. While this tweet doesn’t really hint at the outcome of this stunt, a more appropriate homage to the films may have been paid at home in the bedroom. Either way, the audience was treated to a double feature.


Mapping Out Their Future

This proposal really takes the cake in terms of energy expenditure. A Boston man chose a bike route on a map that spelled out “Marry Me”. He then actually biked the route himself, while tracking his ride on his phone, which he then shared with his girlfriend. He said the route in question was extremely hilly, making for a strenuous ride. As his girlfriend studied the map, puzzled, he zoomed out and got down on one knee. She said yes.


Marriage On The Cheap

If you’ve ever been so excited by the possibilities offered by Walmart’s low prices, you too may have considered starting a future while in the middle of shopping with your significant other. It seems this man just couldn’t wait to get home to ask this woman to marry him. As they always say, if you really wanna seal the deal, buy your ring at Walmart and ask your lady for her hand in front of the checkout counter.


Home Run Ring

This guy was so gung ho about proposing to his girl, he didn’t even care that his sign was in the background, rather than the spotlight. While most wait to hold their proposal signs until the camera focuses on them in the crowd, this guy made sure the viewers at home had a clear view of him, even in the middle of the game. It almost makes us wonder if Jess was one of those at home viewers.


Jumping The Gun

While it’s traditional to write “Just Married” on the honeymoon mobile, this guy is getting a head start by asking his girl to marry him over his junky, beat up car. Who knows, maybe that’s her style, but at least he was attempting a grand gesture to the best of his ability. When you’re young and in love sometimes the only tools in your arsenal are a 30 year old car and some window paint that we sure hope is washable.


Ballpark Engagement

Gert might wanna meet the guy above who wrote on an actual cow to ask his sweetheart to marry him. What’s not clear is if Gert paid the bull to hold his sign asking Andrea to marry him or if Gert is the man behind the bull costume. We really hope it’s the latter, since it’s always a good idea to ask your loved one to spend the rest of her life with you when you’re at work.


No License To Wed

This guy might have wanted to talk to his partner about a potential marriage before taking the time and effort to put together such a public display of affection. We wonder if it would have gone slightly better had he not provided an alternate option (or at least not written it on his car). Given that this picture ended up on the internet, he may not have been too embarrassed by his rejection. Or he has some pretty mean friends.


Out Of This World

This proposal takes a serious amount of good timing. On top of booking the skywriter, this guy also had to make sure, he maneuvered Alina to the right place at the right time, and that he and the sky writer were on the same page as to where they should be. He also took the risk that everyone would be where they should be, but there was still the chance that Alina would be miss the stunt by being absorbed in something else.


No Dumping Allowed

This guy decided to test out this lady’s willingness to be civilly disobedient by proposing to her in front of a no dumping sign. Unfortunately for him, this lady wasn’t about to heed a sign about not dumping garbage, and it looks like she gave him an emphatic, “no”. Maybe next time he should plan a slightly more romantic proposal that’s not in the shadow of an overpass. It might also help if he found a willing participant first.

Will You Emoji Me?

Welcome to the information age, where a romantic proposal can be had via text, so long as your emoji game is on point. This guy was more than happy to ask his lady to marry him with the help of a number of cartoon depictions, to which she seemed to respond with an enthusiastic “yes!”. We wonder if this technologically inclined pair has actually ever met, or if their entire relationship has taken place over the internet.


Spoks Of Love

In another Trekkie incident, a mega fan managed to score a picture with the original cast of the show at her local Comic Con, but as they were about to snap the photo, her enthusiastic boyfriend jumped into the frame and asked her to marry him. While the girl seemed pleasantly surprised, the cast’s reactions ranged from surprised, to indifferent, to mildly appalled in the case of the late great Leonard Nimoy. It seems unlikely any of the cast members wanted a wedding invite.


Seeing Stairs

In a series of odd and hilarious proposals, this may be one of the weirdest yet. With either a friend or passerby on hand to capture the moment in amateur, cell phone quality, this photo may just be pointing to the sheer spontaneity of the moment. If this guy planned to propose on the roof of an empty parking deck under the cover of darkness, we hope there’s some meaning to this particularly creepy spot for this couple.

I Choose You!

Pokemon cards’ popularity may have peaked in 1997, but that doesn’t mean there aren’t still a few nostalgic fans floating around 20 years later. This special diamond card was slipped into a regular Pokemon deck, however, the inscription almost comes off a little foreboding. It reads, “Will you marry me? If answer is yes, game is over and you win a husband. Forever.” Perhaps its the ominous period following the “forever” or the fact that forever should be implied in a proposal, either way, hope it works out!


A Very Soggy Proposal

If ever you wondered if your significant other would be most likely to agree to marry you after a warm, relaxing shower, you could follow in this guy’s footsteps and hang the question on a custom made shower curtain. Of course, in this case, there’s no evidence that he left a method by which she could actually respond to the question. Unless, of course, a verbal response would still be accepted in lieu of shower curtain markers.


Mario Go

This Nintendo lover had a sweet surprise for his girlfriend. He dressed up the ring box like a piece from their favorite game, one that usually gives an extra life or temporary invincibility. With a picture of Mario and Princess Peach set  in the box, underneath were two rings, a diamond engagement ring that said “Player One Ready” next to a white gold wedding band above an inscription reading, “Player Two Press Start”. This is a sweet nod to a couple’s shared pastime.


Jedi Mind Tricks

Star Wars fans take heed. Presenting a card with a photoshopped picture of yourself holding a ring and a lightsaber that says “Lisa McBrayer, will you marry me?” is probably not quite the romantic gesture your lady (or man) had in mind. Though if she loves him enough, Lisa McBrayer hopefully appreciated the work this guy put into taking this picture with a lightsaber. In our opinion, it would have worked better if he’d gone for the full jedi.


A Very Moving Question

One trucker wanted to take full advantage of the perks offered by his job, and decided on a drive by proposal, with a large sign hung from his moving truck asking Tanya to marry him. Judging by this photo, he seems quite confident that she would respond positively to his efforts. We just hope he drove slowly enough past her house that she could actually read the side of his truck, and that the sign was facing the right direction.


A Game Of Rings

These nostalgic game lovers must be real connoisseurs of vintage gaming if they happen to 1. have an original Contra cartridge laying around and 2. if Contra is a game that’s meaningful enough to the couple that placing a ring on the top of it would be taken as a grand romantic gesture. We just hope that if this couple are such big gamers, they have a full blown arcade wedding complete with the most popular vintage games and unlimited rounds of gaming for all.


Highway To Happiness

It’s pretty unclear from this billboard who this drive by proposal was addressed to. We can only imagine that it was the final step in a complicated scheme, enacted over a series of hours that culminated with the lucky girl i seeing the sign as she drove by in a clear nod to her man’s intentions. Otherwise every person who drove past could have possibly imagined it was for their benefit, which may have led to a lot of unnecessary relationship tension.


A Hollywood Ending

When you have the power of Hollywood supporting you, it tends to be easier to let your creative fancies get the best of you. This one actor, Justin Baldoni, of Jane the Virgin fame pulled out all the stops to propose to his girlfriend. His scheme included planning an evening at the site of their first date before telling her that he was running late. A ruse to screen an action trailer cut with a song and dance routine in order to propose.


Written In The Stars

When two hardcore Trekkies decided to make the jump, one girl’s boyfriend decided to add a little something extra to his proposal: by including a little taped on picture that says “Engage” with the ring. Hopefully this girl appreciated her boyfriend’s geeky little nod to Star Trek, since a real fan should always appreciate Spock telling them what to do. Too bad he didn’t actually write “engage” in Klingon. Now that would have been an interesting and weird engagement.


A Bunny Way To Get Engaged

It’s hard to say which chain this sandwich came from, but for any food lover, a proposal in their favorite chicken sandwich is a surefire way to seal the deal. After all, if you can’t bond over food, then what ground does your relationship even stand on? Luckily for Dennis, he knows Ann well enough to know that planting a ring in the top of her sandwich bun would be seen as the ultimate romantic gesture.


No Help From My Friends

If ever you consider it a good idea to enlist your friends in a scheme as important as an elaborate engagement, maybe have them practice a little first. This motley crew was entirely unprepared to adequately help this man ask his girlfriend for her hand in marriage. Next time he should either choose better friends or make sure his friends understand which direction we read English. For his sake, we hope Brittany thought it was cute.