So it was two Christmas mornings ago and we has just finished opening presents. Everyone was eating, drinking, and having a good time. It was a wonderful Christmas and it was the only time other than with my own family that I felt like I belonged. Samantha is sitting on the floor with my legs wrapped around her while I am on the couch. She jokingly says, “I am so glad you didn’t ask me to marry you today.” I look down at her with a frown, I looked upset. When she saw my face all color drained from her. It never occurred to her that I just didn’t ask her yet. She starts to tear up and I held my frown just long enough to know I went too far. I started to laugh. She didn’t. It was just another one of my silly jokes but this time… it wasn’t really a joke. I wanted to marry this woman. I can’t even remember a time when I didn’t because I felt like I had already made that decision a long time ago. But Christmas was when I decided I would ask her. Where? When? How? I didn’t know. I just knew I would.
So I got a ring. A halo oval cut engagement ring. I had never seen something shine like that before. It was gorgeous. My Mom said so. My Dad said so. So now it was time to get the family’s blessing. First was her father. He was never in the same place for more than a few days so meeting up with him was not an option. I decided I would just have to make it a phone call. So I buckled in for one of the most nervous phone calls I have ever made which, in hindsight, was stupid. Randy is the kindest and most gentle man I have gotten to know. When I told him my intentions he had nothing but support and good things to say. He was glad that I made his daughter so happy and couldn’t think of anything better. I almost cried right there on the phone because I never had so many nice things said to me by another man. Any and all doubt was removed. Shortly thereafter I went to her mother’s house to let the rest of the family know. They were all ecstatic. Shelley was over the moon and Hannah couldn’t be happier to be one step closer to being an aunt. Rick congratulated me and told me how happy he was for us. That was it. I was ready. Except… how do I do it? When?
So I had a lot of ideas over the months. Valentine’s Day? No. Take her out to dinner? Nah. I settled on our 3 year anniversary. I had planned a trip out to Galena, Illinois for our anniversary. We booked a room at a bed & breakfast. It was cozy. We would spend the day together exploring the town, go to dinner, and then that night in the room with candles and a hot tub, I would ask her to marry me. That never happened. Sure we went to Galena and had a blast but three weeks before that, during the week leading up to my parent’s big 30th wedding anniversary party my mother asked me, “Are you proposing to Sam at the party?” I told her, “No.” I had spoken to my grandma during the week about the party and she asked, “Are you proposing to Samantha at the party?” I said, “No.” The night before the party I was laying in bed with Samantha and she asked, “Are you proposing to me tomorrow?” Again, I said, “No.” But that was silly. Why wasn’t I? My whole family was going to be there to witness us. My Grandma, Mom and Sam all thought I was or at least had the idea in their head. It really did just make too much sense. So that morning, I got the ring and decided I was going to ask her at my parents anniversary party.
The party was going great. We finally got the ricotta noodle salad debacle figured out (Don’t ask). It was a good time. My father announced that the bowling lanes were going to be open for a few hours. There was my chance, before everyone left to bowl. I took the mic from my father, stood on a chair, and I think… I think I proposed to Samantha. I am not exactly sure what came out of my mouth but the ring was on her finger, my mother was crying, Sam was crying, I was crying, even Johnny (my brother) was crying. I did it. I was engaged to the love of my life. And now we are on this adventure to become one and start our life together. I have no idea what is in store for us now but I know that we will be ready and nothing can ever come between us. I love her more than anything and can’t wait to fumble through the rest of our lives together.
— Ryan Dillon