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How He Asked started in 2011 as a way for couples to share their marriage proposal story with their friends and family. They still do that ( share yours here ), but now we have a few other tricks up our sleeve – all proposal (or love) related, of course – too. Their Instagram is one of our favorite accounts since they tell stories of how couples meet, get engaged and their love stories. We like to be part of the love story but a little farther down the road.

How we met: I started HowHeAsked.com about three years ago. A year before that, I met a Chilean Miner at a halloween party. In real life, the miner’s name was Greg.

Greg met a home-wrecker that night; I was dressed in a Home Depot apron that replaced the word “depot” with “wrecker”. He always says I caught his eye the second I walked in, but I think the fact that the apron was just about all I was wearing on a freezing night in New York City caught most everyone’s eye at the party too.

Nonetheless, I made my way over to where he and his ice axe were sitting and we talked long and hard enough for him to ask for my number. Somewhere in the middle, we also took a group photo. I love that we ended up next to each other in it and still laugh at how confidently his arm around me was.

The next day, my phone rang and it was the first time I’d set up a date with someone over the phone. Greg’s boldness impressed me from the beginning and continued to during our first date and beyond. On our third date, he rented a ZipCar and we went hiking outside the city. I still remember the feeling I had driving together. Something felt right. There was some sort of peace in my heart. Some sort of reverse déjà vu. I knew it would happen again.

Of course, we continued dating; my favorite part being the morning kisses (for Greg only: kiffes) I would run down in my winter pajamas for during his 7am runs.

In the middle of it all was Thanksgiving. I went home to Florida, but booked a shotgun flight to Colorado with my snow-addicted dad after we saw a crazy weather forecast at the mountain we’d been skiing at for years. That trip convinced me that I had to do a ski season one year, and this was my year to do it. Three weeks later, Greg was helping me paint my purple walls back to white and I was on my way to Steamboat Springs until April.

Greg and I didn’t stop talking and he visited me a few very fun times. We were like kids together skiing all over the hill, having snow fights, and all the other things two can do in lots of feet of snow. We started inside jokes, created our own language, had wine by the fire and were both happy to find someone else that loved all these mountain things.

On the last day of one of his visits, Greg kinda sorta slipped and said something along the lines of “I’m sad to leave but happy to leave knowing we love each other.” We hadn’t said the L word yet, but I guess my future husband was feeling bold again.

 

Like I did for the mountains, however, Greg also started to have an environment change in his heart. He wanted to leave New York and move to San Francisco. When he told me, the first thing that popped out of my obviously logic mouth was, “Well! If you’re quitting your job anyways, quit a few months earlier and go to India with me!”

In a second, he agreed. But only if I agreed to move to San Francisco with him after.

To make a long story a little shorter than it could be, we went to India, Nepal and China within 6 months of knowing each other, moved to San Francisco three months later (where HowHeAsked was born), moved back to New York together, skied many more days, traveled to many more countries, and had many more of those “something feels right” moments. Four years later, I’m a giddy girl thinking how perfect a partner that Chilean Miner became for me.

How he asked: There are two questions I always get asked first about HowHeAsked. Why did I start it and is your boyfriend scared to death to propose to the girl who has seen it all?

Answer one: I started it because a friend of mine got engaged. I loved seeing her irrevocable smile when it happened and I later loved telling people who never even knew this friend about how her now husband asked. It was as simple as that.

Answer two: I have seen it all, yes, but that “all” belonged to other people. Whenever my proposal would happen, it would be different because it would be happening to me. It didn’t matter what I’d seen. I’d never seen my handsome guy look me in the big brown eyes, tell me things I now don’t remember, and ask me to marry him.

My “scared-to-death” boyfriend didn’t have to amount to anyone or anything the proposal girl had seen. He just had to ask.

The only thing that seeing thousands of proposals every year signed me up for was that I felt absolutely positive that I would pick up on it before he did. I was sure I would piece it all together, and ruining my own surprise was the only thing I thought I was destined to do.

That certainty in place, it was December 18th. Greg and I were eating pancakes with my parents and peeking out the hotel window to see how much new snow was hitting Beaver Creek. No one was being particularly nice to me and my dad even made some typically annoying comment to Greg and I about my impatient wait for you know what question. It wasn’t the first time my dad (or I) joked, teased or pressured the case, so I thought nothing of it. Greg laughed, I made a sour face, and we all headed out to ski. saladsup.com

The day started out truly ordinary. I snapped a shot of my main squeezes: ordinary.

A few of my dad’s friends met up with us to ski: ordinary. Skiing with a big group of guys started to annoy me: ordinary. We met my mom for lunch: ordinary.

The day was like all the 30+ other days Greg and I had skied together before.

So when my dad told us this was his last run, and Greg and I agreed to head in as well, my mind was made up that I was ready to be off the hill. The slope we took happened to be a hard one, my legs were tired, and on our way down, Greg yelled that he needed to fix one of his boots. We pulled over towards the tree line and I started to squat and wait for him to get back in shape. After a few too many seconds of holding myself up, I kneeled to the ground and turned to check on Greg who was a few feet below me.

I saw both his skies unclipped at this point and, confused, I asked him what happened? He didn’t answer.

“Honey, what happened?” I said somewhat urgently.

He still said nothing, but started to hike up the mountain towards me. Of course a lot of stuff ran through my head. I kinda looked to the left and right but it was hard not to look directly at his face as I seriously freaked out on the inside. Was he going to tackle me and kiss me like we did in Steamboat? Was he going to sock me with a snowball? Was he going to propose!?!!???

So I started asking more questions. The same question over and over actually, just in different tones.

What are you doing?
Greg, what are you doing?
Babe stop, what are you doing?

He said nothing until he was kneeling right in front of me taking off my goggles for me.

He put his hands on me, looked me in the eyes, and shakingly said my name….

 

“Stace” is all I remember hearing (though he said much more) except myself screaming ohmygod and a lot of the less appropriate common surprise phrases. He must have said the words will you marry me, but again that darn shock got me.7

Then he started unzipping his jacket and he pulled out a box. My hands covered my face, I was scared to look, but of course I did and then the graceful words “holy shit” came out as I swung my arms around him.

I was shaking and so was he and he asked if I said yes. We kissed and the most confident yes came out of me.

He put the ring on my trembling finger and told me he wanted to propose in the place we fell in love. I told Greg I couldn’t believe it and then he told me John (one of my dad’s friends) was taking pictures from a far. I waved to John and still wasn’t sure it actually happened.

When it was time to ski down together, so many questions were racing out of my mouth. Do my parents know? When did you get this ring and where? Are you still serious right now??? I felt like I was on a snowboard for the first time because I was so shaky I couldn’t concentrate. I could have fallen over any second, though it didn’t slow me down. I couldn’t wait to see my parents and tell them they were going to be father-and-mother-of-the-bride, or give my new fiance another kiss!

At the bottom, to top it all off, my mom was holding a celebrate sign and I noticed another girl holding the other side of it. It was my best friend Beth and words can’t describe the excitement and tears I had to see her there.

Getting engaged is so exciting because the love swells up from everywhere. From how my fiancé made me feel, to seeing watery eyes in my mom and dad, to being in the loving arms of Beth and my sister who came right after too, to hearing screeches on the phone from more amazing friends and family, I truly felt on cloud 900.

We celebrated with one more surprise from Greg’s friend John, a lot of toasting back at the hotel, and a gorgeous engagement dinner to follow. I have never felt so wildly happy and every time I think about December 18th, which has been every other hour since, I’m brought right back to that place of pure, indestructible happiness.

I will forever smile on the beginning of our marriage, and I will forever love how my Chilean Miner asked.

By John Macaluso February 13, 2025
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