Emma and Michael

Marriage Proposal Ideas in Thomas Point Shoal Lighthouse

How We Met

It was three weeks before my Senior Prom. I went to an all-boys school in Baltimore and feeling the pressure, I asked my friend, Beth, at the nearby all-girls school to set me up with one her friends. She suggested I look through her pictures and let her know who I wanted to go with. I pretended to look but I already knew who I wanted her to set me up with. I sent a photo of Emma who had caught my eye throughout high school but I never had a chance to meet. Beth spoke to Emma and connected us on AOL Instant Messenger (ha!).

We talked for about an hour before I pretended that I had to do Spanish homework so I could get Emma’s number. I took notes on talking points (didn’t want to mess this one up!) and called her later that night and officially asked her to prom. Note: This won’t be the first time she says yes!

We talked on the phone and by text a lot over the next three weeks and finally met in person on prom night, May 3rd, 2008. The best way to describe it is magical. I always say I was on top of my game that night but looking back, I really wasn’t. I was late to pick Emma up because I felt like I needed to wash my car a second time that day to make sure it was clean AND I cut myself shaving and reopened it in the middle of dinner so had to disappear for 15 minutes to take care of that.

After that Prom night, we both knew we had something special. The only problem was it was the end of high school and I was going to Georgia Tech in August and Emma was going to the University of Maryland. Dating long distance was difficult but thanks to Skype and empathetic roommates (Thanks Ben and Mori!), we got through it.

After a year at Georgia Tech and deciding engineering wasn’t for me, I transferred back home to Maryland. We got to spend the next three years in the same state before we each got our dream jobs out of college. The only problem was that Emma’s dream job was with an advertising agency in Manhattan and my dream job was with the Athletic Department at Maryland. We spent the next 3 years dating long distance (again) and becoming very familiar with the NJ Turnpike.

Almost a year ago to the date, I moved to Manhattan and we agreed to never do long distance again!

how they asked

I am an Event Planner so I frequently come up with elaborate “surprise days” for Emma. I will wake her up on a Saturday and tell her what to wear and what to pack and then we will hop in a car and experience a day full of surprises.

I was in Toronto for work for most of the week leading up to the proposal. I was flying back Friday afternoon and then we were going straight to the Beyoncé Formation Tour at MetLife Stadium. But we didn’t have any plans on Saturday, so I suggested we do a surprise day because I was able to get a reservation for something that I have been dying to do.

Engagement Proposal Ideas in Thomas Point Shoal Lighthouse

After waking up at 6:30 AM on Saturday to pick up the rental car, I got back into the city and woke Emma up to get ready for the day. When we went outside, I had Emma guess which car I rented — which was the brand new Jeep Grand Cherokee (Emma’s first car was a 1996 Jeep Grand Cherokee).

We were driving to Annapolis, MD (a 4 hour drive from New York) but Emma had no idea where we were going. To distract from the long drive we relived the Beyoncé concert from the night before and listened to the entire set list. At one point during the ride Emma noted: “It will be so easy whenever you want to propose to me. You will just wake me up and tell me exactly what to wear and I will just follow along, completely clueless!” I turned the music up louder…

Things were going smoothly until Hurricane Matthew decided to make an appearance and it began to rain just before we pulled up to our first destination. I was clearly a little flustered by the rain so Emma asked if everything was okay. I said, “yeah, definitely. It isn’t even raining that hard. It is just because we are going 70 mph…” Emma quickly interjected and said “nope, it’s actually down-pouring!”

We got to our first stop, Great Frogs Winery in Annapolis and sat down for a wine tasting in their beautiful (covered) barn.

Then we headed to the Annapolis Maritime Museum where we hopped on a boat for a private tour of the Thomas Point Shoal Lighthouse. The lighthouse is 1.5 miles offshore in the Chesapeake Bay and sits on a sand bar alerting boats of shallow water.

The lighthouse staff did a great job of selling the tour and told Emma that they had a few last minute cancellations because of the rain and it would just be three of us on the tour. They explained that the third person was a photographer with a local magazine that was doing a story on the lighthouse. Shout out to Kimberly Florence Denn for being an awesome actress and selling this story.

We left the dock and started the 30 minute boat ride through the Chesapeake Bay to get to the lighthouse, where we were given a tour. Thomas Point Shoal Lighthouse is basically a two bedroom house complete with a kitchen, parlor, office, out-house, balcony, a bay view and a light on top!

Wedding Proposal Ideas in Thomas Point Shoal Lighthouse

Emma's Proposal in Thomas Point Shoal Lighthouse

Proposal Ideas Thomas Point Shoal Lighthouse

That “light on top” only has space for one person to view it at a time. So when Emma went up, I quickly discussed where I would propose with the tour guide and photographer. The rain had cleared up so once Emma came down, we quickly went outside on the balcony. I asked the “magazine photographer” to take a quick photo of us but before we could take the photo, I grabbed Emma’s hands and turned her towards me.

I started with “I have an important question to ask you” and Emma’s immediate response was “Are you kidding me?!” Her last words were simply, “Yes.”

Where to Propose in Thomas Point Shoal Lighthouse

Emma and Michael's Engagement in Thomas Point Shoal Lighthouse

On the boat ride back to the Maritime Museum, I came clean on everything I lied about for the past two months and hinted that I still might have a few surprises up my sleeve.


Once back at the Museum we took a few photos with Kimberly and embraced the rain!

Then we drove to her Aunt’s house 10 minutes away. I told Emma that we would just swing by to say hello, call our parents and do a quick outfit change. On the way, I gave Emma nail polish (I luckily grabbed the right color!) so she could do a quick touch up before any more photos.

When we walked into her Aunt’s house, she was surprised by our closest family and friends, including her brother who is away at college and my sister who lives in San Diego. The celebration was complete with two custom engagement SnapChat filters.

It would make sense for the surprises to stop there but next we drove to Baltimore where our best friends had rented out the 2nd floor of a bar in Locust Point. The bar was covered in photos of Emma and me from the last 8 years and she walked into a room full of friends.

Special Thanks

Kimberly Florence
Wedding & Portrait Photographer