Alex and Jess

Where to Propose in Charlottesville VA

How We Met

Jess and I officially met in November of 2014. I was dating a friend of hers, and the friend introduced me to Jess at the gym we all worked out at. Jess, at the time had long brown hair. I remember thinking how cute she was! Her friend and I only dated for a short period of time, so I only met Jess the one time at the gym. Fast forward to July of 2016. Still working out at the same gym, I noticed this cute blonde girl, and I noticed she too had noticed me. Unbeknownst to me, Jess had dyed her hair back to her original blonde color, so I had no idea this was the same girl. We continued to share glances for the entire workout, until she departed the gym for the day.

Since I decided not to break one of the golden rules of approaching females at the gym, I decided not to disturb her. So, I asked a trainer at the gym if he knew her name. Embarrassed to say, I felt compelled to look her up on facebook and send her a message. At this time, although I hadn’t realized it was the same Jess I met before, she remembered who I was. She accepted an invitation from me to a date.

This date was definitely no ordinary date… She had informed me that she would enjoy to join me for a drink, but she was moving into a new apartment and had a lot of new furniture to put together. So, being the crafty, smooth guy I am, I decided to go out on a limb and offer my handy man services to help her install her new furniture. Not knowing much about tools or assembling furniture, she accepted my offer.

For the majority of an afternoon, I spent my time with her and her roommate installing an entire bed set, dresser and couch for their apartment. Little did I know at the time, I was later informed that her ultimate goal wasn’t to truly get to know me, but to have her furniture installed, labor free by a guy trying to impress her! Little did she know that she would take an interest in not only my building skills, but my character as well and we would end up engaged over a year later!

How He Asked

I had been planning a proposal for a few months, I was just waiting for an original idea to dawn on me that would be an epic surprise. Jess and I spent the entire year of our relationship, living in Missoula, MT. Jess was planning on attending law school in the fall to one of the law schools that suit her needs. Unfortunately, none of the law schools were even remotely close to Missoula. She was informed that she had been accepted into UVA Law, located in Charlottesville, Virginia (of course it has to be the school on the other side of the country!).

I was trying to formulate a plan for a proposal before she left for school, but nothing came to me that would be an epic surprise. We drove across America in August to send her off to Law school, and I would return back to Missoula where I live. September is special for me because one of my passions in life is elk hunting, and the season opens in September. I usually cannot be found for the entire month, because I’m in the back country chasing elk.

Jess had joined a softball program that her school puts together for the students, and unfortunately, because of elk season and work, I was unable to attend any games. It was at this time when I decided to set my selfishness aside and skip the later part of the season and fly down to surprise her at one of her games. This was no ordinary surprise. I had contacted her school, team captains, faculty and even the dean to help me organize a proposal for Jess. Everyone was overwhelmingly excited to help with my proposal.

I contacted a local DJ in Charlottesville, and asked if he would be interested in playing our song from the stands when she walked up to the plate. He too was excited and accepted to be apart of the special day. So, I purchased a ticket and flew across the country the day before her game. I explained to her that I would be out of cell service, chasing elk deep in the mountains. She wished me luck two days prior and to her knowledge, I was off to the mountains. I arrived in Charlottesville the evening before her big game.

The morning of, I met up with the DJ, team captains and faculty at the field and we went over how this would all play out. There were a large grove of trees in the outfield, and we decided I would hide in the trees until she came up to bat. As I sit waiting, I could vaguely see her team take the dugout to bat. Jess was batting third in the lineup.

Marriage Proposal Ideas in Charlottesville VA

After the two batters got on base, I heard the DJ start our song. At this point, I walked out of the trees, into center field, and begun walking slowly to home plate, roses in one hand, ring in the other. Jess, standing in the batters box, confused as to why our song is playing and the team isn’t pitching, finally spotted me walking onto the field. she dropped her bat and began to jog to meet me in center field. When we finally met, she said, “how are you here?!?”, as I handed her flowers and dropped to a knee while the entire field erupted in applause!

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Special Thanks

Jill Winter | 
Planning