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Anna & Samuel

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Anna Castleberry

and

Samuel Ellenwood

June 29, 2025

Fayetteville, AR
4 days4 d46 minutes46 min6 seconds6 s

How We Met

October 28th 2023

Anna's Point of View In October of 2023 I had a hike planned with Emily and Shelby, unfortunately it was raining that day so we ended up going to lunch instead. Upon conversation, I told Emily and Shelby that I had a coffee date later that day. We talked about the date (Sam), and I told them I wasn't super keen on going on any dates because I was very happy single. They encouraged me to go (as they had a good feeling about him), and said I would at least get to meet someone new. When I began getting ready it was still raining so I put on a cozy warm outfit. I drove up to Airship and began to get a tad nervous, because this was something new I had to do. I told myself "Hey at least I get coffee". I walked in and Sam had a sweatshirt with a giant smiley face on it, so he wasn't super hard to spot. Talking to Sam felt like I was talking to a long-time friend, but in reality, it was a man that I was on a date with. I began telling him a story about my sister sending me pictures of her dressed up as different Halloween characters. The way that he listened and asked me questions was intriguing. Our conversation flowed so well that I was curious to see what would happen if I didn't say anything else after he finished his initial thought. We had only silence between us for just a moment, but it wasn't awkward...it was more comforting than anything. One of my favorite things my Maid of Honor, Hayley, and I do is exist in each others presence, and sometimes this includes silence. When I knew Sam could do that with me, it made me smile. Our talking continued followed by a second date proposal. Bold, I thought. But I knew the answer I would give was yes. There was absolutely no part of me that believed that this first date would change my life. But it did, in the best way. The more time I spent with Sam the more I knew that he was the man I had prayed for. A godly, supportive, loyal, good-natured man who could take on an independent and determined woman like myself. Sam's Point of View I had matched with Anna on Bumble and the first message I sent was asking about a prank she did on her office manager and hiding over 200 tiny ducks in the office. I quickly found out that she likes to hide tiny ducks to prank her friends and family. I found myself enjoying talking with her so I asked her out on a coffee date at Airship. That weekend was Jonny's bachelor trip. There I told him, Clay, and Daniel about my date with Anna. I was not expecting a lot as I was finding a good pace in my single life and confidence in it. I had planned to get dinner with a guy from my small group afterward in case I needed an out. It was cold and wet so I wore nice jeans and a sweatshirt from church that had a smiley face on it. Anna showed up a few minutes later and immediately hugged me. Her joy radiated from her face. She dropped me into the conversation she was having with her sister's Halloween costumes. It felt like we did not just become friends immediately but that we had been friends forever. After about forty minutes of talking, I wondered what would happen if I let there be some silence. She seemed to have the same idea as we stared at each other's eyes for a good thirty seconds. I did not know what the future held, but at that moment I knew that I wanted to take her on another date, so I asked halfway through and she gave a cool reserved yes that made me even more interested. Before I knew it, our coffee date was almost two hours and I was about to be late for my dinner with my small group guy. We parted ways and as I was regretting making dinner plans that cut short our date. As I walked to my car Anna called my name. I turned around and saw her in her rain boots jumping into a puddle. I gave out a laugh and knew that I wanted to see her not just for a second date but a few more after that.

The Proposal

November 8th 2024

It was Anna and I's one-year anniversary of dating. I told her mom, Callie, Emily, and Shelby a month before I was planning on proposing. I told them I planned to propose at Airship, where we met, on our anniversary and then to have a surprise engagement party afterward. They were all on board and helped out a lot in getting it all ready. I told Anna I had reservations for us at a fancy restaurant that night and asked if she could get off work a little early. The excitement and nervousness began to build about an hour before I saw her. When she got off work I met her at her house where she gave me an anniversary gift of a Fossil watch. As I put it on she asked me why I was shaking, I told her because I was so excited about the gift. On the drive there she was telling me about her day and I was trying to listen while also trying not to have my heart burst out of my chest. It then started to lightly rain like the day we met. We began to head the opposite way of the restaurant. She asked about the location and I told her it was in a new location. We then pulled up to the empty Airship. "I don't need coffee," she said. "Why are we here?" "Let's just go in for a second and check it out," I said. I thought at that moment she would know but she didn't yet. She got out and I slipped the ring into my coat pocket. We walked up to Airship and saw a line of ducks leading to the front door. (We connected through a prank she pulled on her friends where she put tiny ducks everywhere in their office.) Inside tiny ducks were decorating the coffee shop and one of our favorite songs, "Steal the Show", was playing. She kept asking what was happening. I led her to where I knew the photographer could get a picture of us holding her hands and looked into her eyes. Through tears and bumbling words, I told her a few of the big reasons I love her, her firey spirit, her Christlike joy, and her perseverance of faith through trials. Then through sobbing words, I asked Anna to marry me and she said yes!

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