Shasta and Whitney

How We Met

Whitney and I had been friends all through college. What I mean by friends is I thought she was hot, and she thought I was a dork. That’s what “friends” means in college right? Her smile melted me from the inside out. She always has had the most incredible and loving personality. She was someone everyone was magnetically drawn to. We met through our mutual friends and spent multiple times together laughing over her quirky jokes or talking about Disney. We were always dating other people, but everyone in the room always knew that I had the hots for the blonde babe at the party. Whitney watched my heart get broken over and over again, and I watched her looking for love in all the wrong places.

Engagement Proposal Ideas in Bethany Vineyards/ Engagement Session Video: Cannon Beach

Marriage Proposal Ideas in Bethany Vineyards/ Engagement Session Video: Cannon Beach

Shasta's Proposal in Bethany Vineyards/ Engagement Session Video: Cannon Beach

Where to Propose in Bethany Vineyards/ Engagement Session Video: Cannon Beach

Once we were both single we decided to get to know each other a little bit better. I was in a serious relationship before and wanted a hook-up. Whitney, on the other hand, wanted a serious relationship with me. She was so patient; letting me heal and loving me through the entire process. It started off with just simple dinner dates and soon after came the innocent kisses, and somehow we ended up in Disneyland where I fell in love with her. Her childlike laugh and adventurous spirit finally caught my full attention. Whitney asked me to officially be hers on August 18th of 2014, proposed on September 7th of 2018. Four years of vacations, kisses, houses, and cats lead us to an engagement.

How They Asked

Shasta was BEYOND ready to get engaged, and so was I. We had discussed it multiple times; watching Shasta plan her dream wedding the last four years on Pinterest. In December of 2017, I finally took her to look at rings, and get her sized. I didn’t want her to have any idea it was coming. I bought her ring in January of 2018 and didn’t propose until September. I have to admit, it was fun watching her squirm! She even thought at one point when we were at the Oregon Zoo, that an elephant was going to walk out with a big sign that said, “Marry me?” It would have been too easy, she was always expecting it, and it was hard to sneak it all past her. Every single weekend in August (the month of our anniversary) she expected I would do it, but I made her wait so she was truly surprised. Her brother and his wife were in on the secret, and they were the only two who knew it was happening. I didn’t want our family or friends to know since Shasta figures out everything!

On September 7th, 2018 Shasta’s Sister in Law asked her to come wine taste for her since she was pregnant and couldn’t drink. Behind the scenes, I met her brother and sister at the winery and had set up rose gold balloons hung on an arbor spelling out, “Marry Me?” Shasta arrived at the winery in search of her sister in law only to see all of us in the distance. She was shocked and shaking from head to toe.

When people say you black out and forget everything you said, they are right. All I know is she said YES! It was the best day of our lives, and we couldn’t wait to share our engagement with the world!

Our Video

Watch more proposal videos & follow @HowTheyAsked on Instagram for more stories!

Special Thanks

Baylee Dennis
Photographer