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Anna & Ryan

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Ryan Downs

and

Anna Ashe

October 4, 2025

Chicago, IL
98 days98 d11 hours11 h6 minutes6 min49 seconds49 s

Our Story

If you threw a pig in the air, it would fly right now.

Ryan and Anna met at a Christmas Party in 2015. Anna thought Ryan was very quiet (she was wrong) and wasn't sure if she and the friend group scared him enough with their antics that he would never return to another event. However, Ryan did not just attend other events. He BECAME THE PARTY. The two became good friends, both working on Catholic Young Adult organization boards and being very active at the same local church. They quickly formed a core friend group, which was labeled "The Squad." (Shout out to the Squad). The Squad hung out multiple times a week and went on many adventures, with Ryan's place being the hub. Ryan was always there for Anna, meeting her after bad dates, picking her up when her car broke down, moving furniture, and yelling at her to get down from whatever table she was dancing on. Likewise, Anna was there to talk Ryan out of rash decisions like moving out of state after a break-up, she helped him move, and would yell at him when he flipped yet another car. The two were very close friends, and the idea of dating was weird. As time passed, other friends in the group moved out of state and/or got married. Anna and Ryan made other friends but continued to be each others' "squad," choosing to do most activities together. At one point, Ryan brought up the possibility of being more than friends, and Anna thought that was a terrible idea and was mad that he was potentially going to "ruin everything." They remained good friends and were still always there for each other. Ryan continually stepped up at every opportunity, making any of Anna's boyfriends look bad (which, to be honest, wasn't hard to do sometimes). The friendship eventually evolved to hanging out multiple times a week, talking on the phone on days they weren't hanging out, and even going on vacation together. Anna eventually realized it was worth risking the friendship because she couldn’t imagine doing anything without him. From there, it was the easiest, healthiest, and most fun relationship either of them had. They decided to keep their relationship a secret from most of their friends and hard launched an engagement for the fun of it, with most reactions being "FINALLY." Ryan and Anna look forward to causing just as much, if not more, chaos together as a married couple... and to keeping the original squad together forever.

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