Clear Cut Couples: Anna and Jay

Anna and Jay go way back… they met in 2nd grade when they had the same teacher! They have been friends for about 15 years, and have been together for over 5 years!

Since they were friends for so long before they actually started dating, neither of them can even remember their first “real” date!!  It was probably their freshman year of college. Jay was definitely a party guy and never took things too seriously, so it took them a while to figure things out -- LOL! She says, “I couldn’t be more sure and can’t wait to start our lives together!”


Anna went to grad school and Jay started a new job in a different town so they were long distance. They actually ended up being long distance (nothing crazy - less than 3 hours) for about four years. Anna moved to Chicago after grad school and Jay would visit her for a couple weekends each month. Those weekends are some of their favorite memories together! They love venturing out to new neighborhoods and trying new restaurants. They always joke that the only thing they have in common is liking to eat out for every meal.

Jay proposed on July 5th, 2019. They were at his parents house on the lake for  dinner. The two of them went on a boat ride and Jay popped the question there. He was so nervous, so Anna was pretty sure it was coming!

She had a feeling it was going to be happening on that day and is in love with her ring! She has always wanted a simple emerald ring, even after so many people told her they don’t like that kind of stone. To her, it is different, elegant, and perfect for her style!

They finally both live in the same town- where they both grew up . They went to the same grade school and high school and are so excited to start their lives there together! They will be getting married on May 9th, 2020 at a Catholic church in their hometown. Both of them have gone to this church and school from 1st grade to senior year. They will then have a reception with a live band. Congrats Anna and Jay -- we are SO happy for you!!