19 Proposal Stories That Will Make You Hate Being Single Even More


There are some girls who have been planning their weddings since they were able to walk and talk, but fortunately for my father, I’m not one of them. I never had dreams of pulling up to the church in a horse-drawn carriage in a ball gown and a tiara or having a 15-tier wedding cake at the reception. I always assumed I would get married, but I figured I would worry about all that stuff when marriage was actually on the horizon. I was happy being single.

And then I stumbled upon the Instagram account called How He Asked. My life has completely changed. They post the most perfect proposal stories that will make your heart wish you had someone (besides your cat) to love you. These proposals aren’t your typical basic restaurant proposal — they’re love stories. Stories of how the couple met, how long the groom had been planning, and of course, the incredible photographers who capture the exact moment she says yes. These stories will turn any cold-hearted cynic into a believer that true love (and perfect proposals) exist.

(Wait for the last line ) “I met Katie 9 years ago. I was in high school attending a summer camp at #UCLA, and in typical teen ostentation, my group of friends decided to dress up, act as ridiculous as possible (I was wearing a pink feather boa and a furry top hat), and roam the dorms one night. We hopped on the elevator and were greeted with laughs by a group of girls dresses completely normal. Amid the laughter, Katie and I locked eyes, and something deep inside me stirred, like a dormant fire that was finally allowed to catch. I knew right then in that moment, that I would fall in love with this person. In the context of that night, she will always remember the crazy outgoing, pink boa and hat-wearing high school kid, and I will remember it as the exact moment I came alive.” Photo by Carrie Patricia (link in profile to the proposal)

A photo posted by HowHeAsked (@howheasked) on

“A few months after meeting Spencer, things took a turn for the worse. My dad had been living with cancer for five years at that point, and in October of 2014, the doctors told us there was nothing else they could do. I felt like my life was over – I couldn’t even begin to imagine life without him. I told Spencer he didn’t have to stick around as we’d only been dating for four months, but he stood by my side and cared for me and my dad through the worst moments of our lives. My dad ended up loving Spencer and I knew he wanted to see him become a part of the family. I also knew he wanted to see us engaged before he passed, but I didn’t want to ask anything more of Spencer. When the doctors told us how much time he had, my dad said he wanted to take one last trip together. He picked Disneyland and so of course, when were were there, we went in front of the castle and took tons of family photos. At the end of the pictures, in front of everyone, Spencer grabbed my hands and turned me to face him. I went numb. I knew what was coming, and I could not believe he was making my (and my dad’s) dream come true… The next day, we made the long drive home back to Oregon, and that morning, as unexpected as anything, my daddy passed on into heaven…” You actually need to read and watch the whole story (we summarized it, and there’s a video). The link is in our profile

A photo posted by HowHeAsked (@howheasked) on

“We met at one of her sorority socials and a few nights later saw each other out again. We spent the entire night talking away, and as it winded down, I suggested we do something a little bold. I told her I always wanted to sneak in the @uflorida football stadium and she was totally down. After clearing a couple fences and climbing a few sets of stairs, we were in. We even snuck onto the field and decided to lay down on the 50 yard line and look up at the stars. Well luck would have it that as we gazed into the night sky, a shooting star passed overhead. Wanting to capitalize on this moment, I convinced Samantha it was fate and we should kiss. Little did I know that first kiss, would be my last first kiss. Soon after this precious moment, we were blinded by police flashlights who promptly escorted us out of the stadium. I walked her home, and the next day asked her on our official first date…” aaaaand of course their proposal was on the very same field and our hearts are simply melting at the story – link in profile by @carterfish #gogators #deltazeta

A photo posted by HowHeAsked (@howheasked) on

“I met a boy in an elevator. Not just any boy, but a boy wearing a bright yellow shirt. After finishing up a long day touring the MBA program at Brigham Young University, a boy entered my elevator with seconds to spare. I didn’t even look up, I was “busy” staring at my phone when I heard him say hello. I turned my attention towards him and instantly smiled upon seeng his bright yellow shirt and cheerful face. He caught my attention. As we reached the ground level, we had discovered we both had ties to Annapolis, MD. We said our goodbyes and I thought that would be the end of it. Later that evening, though, I received a message via Instagram from that very same boy. The message went a little something like this: “Hey! It’s Morgan from earlier today in the elevator 🙂 I noticed your name from the name tag you were wearing and instantly regretted not asking you for your number or anything after I left! Couldn’t just let a girl from Maryland go like that…..” by @loivophoto – link in profile to see how their STUNNING proposal went down!

A photo posted by HowHeAsked (@howheasked) on

“Over the past 5 years Jake and I have gone through our ups and downs like most couples, and spent time apart too. I moved to Australia and for a period of time I wasn’t sure if we’d ever be together again, but there was always something pulling me back to him. In the start of 2014 I was diagnosed with MS, Multiple Sclerosis, which led me to move back home to California. The only person I could think about and wanted to be with during this time was Jake. This began a new chapter for us in our love story. Jake was not scared off by my diagnosis but instead told me he knew he had to be with me because he wanted to be the one to take care of me and knew he was the only one who could do that. For the past two years he has been my rock through all the ups and downs with my health. He has been my consistent source of love, strength, and encouragement. Falling back in love with him has been the most fulfilling and rewarding decision I’ve ever made.” You have to read and watch the whole proposal, it’s heartwarming and adorable and there may or may not be a puppy involved at the end too… link in our bio 💕 photo by @brianterada

A video posted by HowHeAsked (@howheasked) on

“After dating for two years in high school, Blake and I broke up for college and went our separate ways for the next five years. We dated other people and went through some very personal trials and tribulations, but somehow we continued to stay in touch and check in from time to time to make sure the other person is doing okay. On occasion we’d grab coffee or meet up at a park nearby and just sit on the playground and talk. No matter how long we would go without seeing each other, our deep connection just stuck around. I always called it “first love syndrome” because no matter what I did or who I dated, I could never ever get Blake out of my head. My heart felt such a strong connection with him that it wasn’t budging when it came to anyone else…” See how the incredibly adorable blogger @livvylandblog and her equally as adorable fiancé ended up reuniting and ulimately get enaged. Link in our profile! PS – This pic wins for best way to announce your engagement. Ever.

A photo posted by HowHeAsked (@howheasked) on

“Mark and I met in grade school. Unbeknownst to me (until years later), I was the first girl Mark ever told his mom he had a crush on. He was embarrassed to tell anyone else because he was in fifth grade and I was a grade below in fourth, and of course in grade school, liking a younger girl was just not the cool thing to do. I do happen to have one memory of his apparent love for me back then, however. It was when his younger brother ran up to me on the playground at recess and yelled, ‘My brother thinks you’re the prettiest girl in the world!’…” OMG this couple and these photos and their proposal (hint – he may or may not have learned a card trick for it)!!! Head to for a regular Saturday morning tear-up (photo by KJM photography)

A photo posted by HowHeAsked (@howheasked) on

“I was on a backpacking trip with my sister, Annie. I’d begged Chris to come along, but he’d just started a new job, so there was no way he could swing it. Annie and I ended up going to six countries in one month. In our third week, we headed to London to stay with a friend of ours, James, who lived there. When we got there, James said he’d been invited to a swanky party that he thought we’d all love. Having no appropriate clothes, my sister and I went shopping all day. We met James back at the apartment, all got ready, and headed on our way. James told us we were meeting a few more friends at St. Katherine’s Docks so we stopped there for a few minutes to wait. Next thing I know, I get a tap on my shoulder….” Link to the video in our profile!

A photo posted by HowHeAsked (@howheasked) on

“It was January 8th and when we woke up, we both realized it was our five-year anniversary. At that point, it was too late to make any big plans so Collin said he would make dinner for us when I got home and the idea was more than great with me. Later that night, I walked into our living room and saw he’d set up a cute tented dinner, with a bouquet of flowers and pillows everywhere. We ate his amazing dinner and then decided to move the coffee table out and our air mattress in so we could sleep under it the whole night. We played board games and talked all night long. It started to get late and we were both fading into sleep when he quietly said, “hold on, I need to go get something…”. In that moment, I knew.” See more of this cute couples adorable tent proposal via the link in our profile! Lucky girl: @alyssamariephoto

A photo posted by HowHeAsked (@howheasked) on

“We met almost six years ago while we were in college. The first time I went to his apartment, I remember seeing this beautiful background picture on his computer. It was a photo of the night sky filled with bright stars and green bands of lights. When I asked him what it was, he told me it was the Aurora Borealis or the Northern Lights. He explained how he studied about them growing up and added in that one day he would take me there too. We spent that entire night talking about our goals, dreams, and travel aspirations, and by the end of the evening I knew that he was the one. Six years later, like he said he would, he took me to the Northern Lights and made more than just one dream come true…” You have to see these gorgeous photos – and read the full story (it gave us the chills!!) Link in profile! by @rmurrayphoto

A photo posted by HowHeAsked (@howheasked) on

“I moved to London to attend culinary school for baking and after the first week of bringing home boxes and boxes of pastries, I knew I had to join a gym. The first day I walked in, I was introduced to one of the trainers named Duncan and I was immediately attracted to him (it helped that he was shirtless at the time). Embarrassingly, in my first class with him, I clumsily took a tumble and he exclaimed, “there’s always one”. Then, a couple weeks into the classes, Duncan tricked me into a first date. He told me that everyone goes out after the Friday workout so I decided to go along that week. When we were headed out the door, he told me it looked like no one else wanted to join this time, so we went just the two of us. During the dinner, I went to the bathroom and texted my best friend “Ummm, I think I’m on a date with that hot trainer I told you about”. The next day, I was back at the gym and overheard one of Duncan’s gym friends ask him why he ditched the group last night. In that moment, I knew I was absolutely tricked into the date…” DUNCAN, you’re killing us. And the proposal is even cuter! Head to the link in our profile to see their London-inspired adorable proposal (and their beautiful @minted save the dates — there’s a discount code in there too!)

A photo posted by HowHeAsked (@howheasked) on

“In September of 2013, I was living in California, but I went to Michigan to visit one of my best friends. She’s a wedding photographer and I’m a stylist, so while I was there, we decided to do a shoot together at a local apple orchard. I told Ashley I’d do all the details but find the models and she agreed. On the day of, Ashley casually mentioned, “One of the groomsmen models is really cute – maybe you’ll like him and my ploy to get you to move to Michigan will finally work!” I was immediately nervous but continued to set up and style the shoot. Then… McCann (the “really cute model”) showed up and, of course, I got the good ole fashioned butterflies. Long story short, he asked me to lunch before my flight left the next day, it was amazing, I live in Michigan now, and we’re engaged….” Oh their proposal is just too cute tooooooo! Link in our profile Photo by @missyalison2

A photo posted by HowHeAsked (@howheasked) on

“Katie told me very early on in our relationship that her #1 bucket list item was to wade in a field of cranberries (yes, like the ones you see in the Ocean Spray commercials). Three years later, we had a trip planned to Grays Harbor and I realized there was a cranberry farm that was along the way. So as we were driving, we noticed it and I suggested we go see it! Katie was adamant about not getting out of the car because she didn’t want to bother the grower during his harvest, but eventually (and thankfully), she agreed. Then, I opened the trunk and Katie saw the brand new waders I’d gotten for her. At that point, she had, of course, realized I had planned this. We got our waders on and walked through the bog, passing our fingers through all the cranberries. Katie was glowing. And I could tell she had no idea that there was more…” Link in our profile to read the rest! Their “how we met” story is so cute and he tells everything so adorably! #boysarecute photo by @TATECL

A photo posted by HowHeAsked (@howheasked) on

“My father passed away five years ago, and our trip to San Francisco (Joe had work and I decided to join to visit my brother who lives there) coincided with the fifth anniversary of his passing. My family and I had scattered my daddy’s ashes on a sailboat under the Golden Gate Bridge nearly four and a half years ago so it’s always been a meaningful place for me. So the week we were there, Joe told me he planned a sunset dinner cruise for us on the bay and I was very excited. We had been on a similar sunset cruise earlier in the year while on holiday, and I had expected it to be the same – sharing the boat with a small group of strangers. But when we got there, the captain told us that the other couples had canceled so we had the boat to ourselves as we headed towards the bridge. As we get closer, the captain asked if we wanted to head to the bow so Joe took my hand and lead me to the front of the boat. I assumed he wanted to clown around and have a titanic pose, but instead, he started getting mushy and I could feel his heart beating into my back as he hugged me from behind and we looked up at the bridge. Before I understand what’s happening he gets down on one knee and asks me to marry him! He proposed where we had scattered my fathers ashes and later explained to me that he wanted it to be a happy place for me too…” Link to all their sweet photos and the adorable story of how they met via the link in our profile! Congrats @joey9prints and @@natasha_emily

A photo posted by HowHeAsked (@howheasked) on

I’m not crying, you’re crying.

[via Instagram]

Image via Shutterstock

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Cristina Montemayor

Cristina is a Grandex Writer and Content Manager. She was an intern for over two years before she graduated a semester early to write about college full time, which makes absolutely no sense. She regretfully considers herself a Carrie, but is first and foremost a Rory. She tends to draw strong reactions from people. They are occasionally positive. You can find her in a bar as you're bending down to tie your shoes, drinking Dos XX and drunk crying to Elton John. Email her: (not .com).

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