Clear Cut Couples: Anna and Trent

Anna and Trent went to high school together, but he was a grade older than her, so they never officially met. However, thanks to Instagram, Anna thought he was incredibly good looking and she sent him a message introducing herself! (AKA she slid into his DMs ;) 

She quickly found out he was living in Colorado permanently while she was still in Illinois. After a few months of casually talking on and off, he told her that he was coming to Illinois to visit family. At that point, Anna was beginning to think that they  would never meet, so she was pretty shocked when he said they should get together for a mutual friend’s birthday in Chicago! They met that night at their friend's party and immediately hit it off. They also ended up going to a Cubs game together the next day as officially their first date. AWW!! As the weekend was coming to an end, it hit Anna that he lives in Colorado and she lives in Illinois. She genuinely did not think they could make a relationship work. Luckily, they are both very spontaneous! After a few weeks of visits to each other’s cities (Fort Collins and Chicago), he asked her to be his girlfriend! Anna’s friends thought she was crazy for entering into a long-distance relationship. The first few months were challenging because of the industry that Trent works in. He had to be away at work for months at a time - so their time together was limited. They succeeded because their chemistry and love for each other was so strong. The first year of their relationship, Anna flew to Colorado 14 times. Thank God for Southwest! 

Right around their ninth month of dating, Trent found out he had been relocated to the US Virgin Islands for work. Anna said, “I was not about to let my boyfriend have all the fun of living on an island, so I ended up quitting my job and joining him in St. Croix on our 1 year anniversary to start our new life on the island. We have been living together now for over 8 months on St. Croix and we could not be happier!”

Trent proposed on Memorial Day weekend at sunset on a beautiful beach in St. Croix. Jack and Isaac Bay is a wildlife preserve so he knew no one would be on the beach. Trent coordinated with Anna’s close girlfriend, who is a photographer on the island as well. When she reached out, Anna thought they were going to help her add more photos to her portfolio, and not that this was going to be an engagement shoot. Trent gave her the biggest surprise of her life when he got down on one knee at the end of the hour-long photo shoot. Anna could not have been more surprised or ecstatic!

They had a running joke that every time Anna asked when the engagement was going to happen, he added another "6 months" to the timeline. At that point, Anna would have been 60 and still not engaged... lol. Needless to say, it was a total surprise, and Anna started crying immediately. When she asked where he got the ring and he said "The Clear Cut" she was so happy! Anna had been sending him pictures of rings she liked from The Clear Cut’s Instagram for months, and it was better than she ever could have ever imagined! He also had the ring hidden in his nightstand for a while – so she was also pretty shocked that it was sitting right there next to her this whole time. She knew she wanted something simple, with a gold band. The hidden halo adds the most perfect detail!! She is obsessed with her new ring.

Because it was such a surprise, they don't really have any set wedding plans yet. She would love for the wedding to be in St. Croix, but ultimately they want all of their family and friends to be able to attend, so they are thinking Chicago 2020. They both have a LOT of friends and family, so it will be an amazing celebration! They both cannot wait to start the planning and are really looking forward to officially starting their lives together! Congrats Anna and Trent -- we are SO happy for you!!

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