Ryan and Caitlyn

Ryan and Caitlyn's Engagement in Skydiving in Middletown, OH

How We Met

We met online as a blind date. I live in Louisville and she lived in Cincinnati. I had the whole day planned out but little did I know it would end up being a complete disaster. I planned to start the date off at a place called Main Event, a recreational venue with bowling, Lazer tag, and arcade games. When we got there it ended up being a sketchy strip club. I then decide to rent bikes for an hour and tour the city, and we end up being a minute late to the bike drop off so they charged me and extra $30 per bike, and to end the night I had a wine painting class I had bought online in advance but we was unable to attend because it was the only night it out of the year where you had to have a special coupon to get in and they are already sold out. Surprisingly even though everything went wrong she was still willing to give me a second date.

How He Asked

After dating a year I told my soon to be fiancé at the time we should go skydiving knowing this is exactly how I wanted to propose to her. Being the overly cautious woman she is, she laughed. 6 months later she agreed to jump out of the plane with me. I could feel her nervousness as me my little sister, and my fiancé got onto the plane. Right before I jumped out I looked at her and lipped I love you and then jumped from 16,000 feet in the air. Little did she know after free falling for 2 minutes as soon at the tandom guy pulls the parachute she would read the words “Marry Me” on a giant 30 by 50 foot tarp, see man waiting for her on one knee with a ring, and be greeted by all of her buddies, that traveled from, Columbus, Cincinnati, and Lexington KY from 4,000 feet in the air. As soon as she landed I dropped on one knee and asked her if she was ready to take a leap of faith out of the plane as she is to take a leap of faith in our relationship.

Ryan's Proposal in Skydiving in Middletown, OH

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