Lori and David

Marriage Proposal Ideas in Downtown Milwaukee, WI

How We Met

David and I met in January 2013, when we were seniors in college. David was a senior at the Milwaukee School of Engineering (MSOE) and was at Buckhead’s Saloon (now Red, White, and Blue) with his volleyball teammates. I was a senior at the University of Wisconsin Oshkosh and came back to my hometown, Milwaukee, to celebrate my best friend from High School’s 21st Birthday at Buckhead’s. As I was at the bar buying shots for the birthday girl, I noticed David and his friend talking to each other and looking at me and my group of friends. I told my friend, “watch, these guys are going to come over to talk to us in 3…2..1…,” and like clockwork, they did. David’s friend starting talking to me first, but I immediately noticed David because of his height and smile. I interrupted David’s conversation with my friend to introduce myself. He said his name was “Dewey,” (his nickname) which I thought was interesting. I asked one of my friends to distract David’s friend by asking him to dance, so I could dance with David. After a fun night of dancing and drinking, I decided to give David my number. I first asked him if he had a girlfriend, and he said no, so I then said, “Here’s the thing: you’re attractive. I’m going to give you my number; use it wisely.” He ended up texting me that night, asking me to let him know when I’ll be in town again, so we could hang out. We had our first date at his downtown Milwaukee apartment in February, where we cooked dinner together (and I learned his actual name is David). After our first date, we both knew there was something special between us. After going on a few more dates, on the last weekend of March (Easter Weekend), I introduced him to my mom and step dad at dinner in the suburbs of Milwaukee. We then went back to my mom’s house for drinks, and I introduced him to my brother. We spent the following day in Downtown Milwaukee; it was a beautiful spring day, so we decided to take a walk to the lake front. We stumbled upon a short pier, just north of a dog beach, where David proposed to me with a Ring Pop, asking me to be his girlfriend.

Where to Propose in Downtown Milwaukee, WI

How He Asked

David and I celebrated our five-year anniversary a month late, due to our friends’ wedding taking place over our anniversary weekend. He had the weekend blocked off on our calendar, but I had no idea where we were going. We both now live in Downtown Chicago, and as David and I started driving north, I asked him if I could guess where we were going. He agreed, and I guessed Downtown Milwaukee; he said yes, but I couldn’t know any other details. We drove straight to the pier where our relationship officially started. As we were walking to the pier, he said one of my anniversary gifts was for us to revisit all of the places that were significant to the beginning of our relationship. When we were on the pier, he had me open my second anniversary gift, which was a “View-Master” that said “I love you” on it and showed pictures of us traveling throughout the years. The last picture on the reel was a picture of the Ring Pop that he proposed to me with five years (and 1 month) ago. Then, when I took the “View-Master” off my eyes, I saw David down on one knee with the most beautiful engagement ring. He asked me to marry him, and of course, I said yes! I then noticed a fisherman who was on the pier taking pictures of us, and when he took his sunglasses off, I realized it was David’s friend Scott! Scott took pictures of us, which he shared with his friend who is a wedding photographer at Feathered Photography to touch up, but he gave us a few to share the news with. We spent the day celebrating with family and friends and went back to the old Buckhead’s saloon (now Red, White and Blue) where it all started and partied all night.

Special Thanks

Feathered Photography
Photographer