From First Date to I Do: Our Wedding Week II Timeline

We often mention little milestones in our relationship — meeting in New York City, moving to Virginia, and so on — but the exact timing can get fuzzy. For Wedding Week Dos we decided to lay out our story in chronological order: how a boy met a girl, how they fell in love, moved south, adopted a chihuahua and started a blog. It’s a simple love story, but one that felt natural every step of the way.

2004

  • June: I began working as an Assistant Account Executive at an advertising agency in New York City.
  • August: Sherry started a month later as a copywriter at the same agency.
  • September: Sherry was assigned to write commercials for the account I managed. We met in passing but didn’t interact much at first.

2005

  • January–May: Sherry kept getting assigned to projects on my account. We bonded over trashy reality TV and gradually shifted from coworkers to friends, spending more time together outside of the office.
  • July 7: What began as a casual after-work gathering turned into an unofficial first date. The night ended with a kiss — and despite what our friends say, I really did kiss her first.
  • Late July: Only weeks into dating, I invited Sherry to visit my family in Virginia, giving her her first real taste of life there. We toured my alma mater, UVA, and she got a feel for the place that would soon become home.
  • October: Our first vacation together was a road trip down the California coast from San Diego to San Francisco with my cousin Travis — one of the best trips either of us had taken.
  • November: I spent Thanksgiving with Sherry’s family in New York — our first official holiday together.
  • December: After just six months of dating we decided to move to Virginia together. There was no hesitation — it felt like the right step.

2006

  • January: We interviewed at the same Richmond ad agency — we liked working together since that’s how we met. Around this time I secretly bought an engagement ring.
  • February: The agency jobs fell through because employers wanted to see us living in Virginia. So we made the move without jobs lined up and planned to find work once we arrived.
  • February 25: We packed up a minivan in NYC, snapped a photo on the way, and arrived in Richmond. We moved into a new apartment furnished with mismatched hand-me-downs.
  • March: Within a couple of weeks I found a job at a downtown ad agency where I still work. Sherry built up clients as a freelance writer, focusing on commercial scripts and magazine ads from home.
  • March 18: I proposed and Sherry said yes.
  • April 22: A weekend of casual house hunting unexpectedly turned into buying our first home — a small brick ranch that needed a lot of love.
  • May 25: We closed on the house and began the long and rewarding process of moving in and renovating.
  • July 7: To celebrate our first anniversary of dating, I surprised Sherry with a trip to the Outer Banks.
  • October: We returned to California for a second vacation, just the two of us. After a week of nonstop togetherness, we were amazed we hadn’t argued once — life felt very good.
  • November 28: After months of searching, we adopted a quirky little chihuahua who needed a home. We named him Hamburger, though he’s often called Burger.

2007

  • January–June: Wedding planning dominated our free time. We discovered that we enjoyed teaming up and doing DIY projects together, and the prep brought us even closer.
  • July 7: Our backyard wedding went off without a hitch. Travis, who had joined us for that first California road trip, officiated the ceremony. We exchanged vows and started our next chapter.
  • July 10–16: We honeymooned in Alaska, a road trip full of adventure and silliness. Our small dog came along and made the trip feel like a family vacation.
  • September: With wedding bills settled, we put some savings toward remodeling the kitchen.
  • September 24: I wrote the first post on a new blog I suggested we call “Young House Love.” Sherry was hesitant at first, but soon warmed to the idea of documenting our home improvement projects. That decision launched the blog and became a place to share the big and small moments that followed.

From that point on, our milestones have been chronicled here on the blog: paint colors, renovation hiccups, decorating wins and everyday life. Looking back, moving cities, getting engaged and buying a house within our first year of dating might seem fast, but every step felt right and never forced. When things line up and you’re sure, it often just makes sense.

Do you have a memorable relationship timeline? Did something between you and your partner happen quickly, or did it unfold slowly over time? Did you meet at work, at a party, or somewhere unexpected? It’s always fun to hear the different paths people take to decide they want to spend their lives together — feel free to share your story.

PS: For a photographic look back at our timeline — including moments from before we met — we put together a slideshow of photos that we displayed at our wedding. It’s a nice visual recap of how all the little events fit together.