Paige and Natalie

Paige and Natalie's Engagement in Chicago, IL

How We Met

Paige and I met in the fall of 2013, and started dating at the end of 2014. We coached softball together for an entire summer as our relationship grew from friendship to relationship. Paige was my best friend first, and to this day still is. We had been dating for about two years when I decided to propose. I said that I loved her after only a few weeks of dating, because my feelings for her were so strong. The first 8 months of our relationship was long distance, and it just made me more grateful to be with her everyday when we finally got together. Every day with Paige makes me feel like I’m at my best, and I decided that I would love for us to both feel that way forever.

The planning was intense, and I didn’t sleep for the whole week before because I wanted everything to go perfectly. The great part of the proposal day was that her and I had a great day together, just being us. That night, the weather was perfect and I took her to a view of the city skyline with our friends and photographer laying in wait. When I knelt down to ask her, I can’t even remember what I said because the smile on my face was so huge. After she said yes, we went to a surprise party where all of our families and friends were waiting to celebrate with us. The night could not have gone more perfectly and I can’t wait to spend forever with this woman!

How she Asked

Paige and I met in the fall of 2013, and started dating at the end of 2014. We coached softball together for an entire summer as our relationship grew from friendship to relationship. Paige was my best friend first, and to this day still is. We had been dating for about two years when I decided to propose. I said that I loved her after only a few weeks of dating, because my feelings for her were so strong. The first 8 months of our relationship was long distance, and it just made me more grateful to be with her everyday when we finally got together. Every day with Paige makes me feel like I’m at my best, and I decided that I would love for us to both feel that way forever. The planning was intense, and I didn’t sleep for the whole week before because I wanted everything to go perfectly.

Wedding Proposal Ideas in Chicago, IL

The great part of the proposal day was that her and I had a great day together, just being us. That night, the weather was perfect and I took her to a view of the city skyline with our friends and photographer laying in wait. When I knelt down to ask her, I can’t even remember what I said because the smile on my face was so huge.

After she said yes, we went to a surprise party where all of our families and friends were waiting to celebrate with us. The night could not have gone more perfectly and I can’t wait to spend forever with this woman!

Our Video

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

Special Thanks

Brian Galligan | 
Photography
Natalie
Natalie