Sydney and Tony

How We Met

Two Chicagoans walked into a bar… well, not quite! We swiped right! In the Spring of 2015, like most single city women find themselves on a Thursday evening, armed with a glass of wine and Netflix, I (Sydney) was swiping across Tinder and noticed a tall, bearded, gentleman with a sweet smile (Tony) who quickly caught my attention. As I was scrolling through his photos, consisting of friends, family and a few nights out, I swiped right to what would become my future husband.

Over the next few weeks, Tony and I messaged each other back and forth learning about each others interests, work out regimens, travels, and Netflix binges for two full weeks before meeting in person. On May 2nd, we decided to grab an early lunch for the first date at Big Star, a local taco spot in Wicker Park.

During our first date, we had an unusual encounter with a man who wanted to sell us a donut and struck up a conversation. Not knowing we had just met, the man had guess we had been together for 3+ years and that we would continue to be together for a long time. (Maybe that was a sign for all the good things to come!) Easing our nerves by putting us in a interesting predicament we laughed off the whole situation over tacos and margaritas.

At the end of lunch, Tony actually suggested we head to another bar up the street to continue our conversation and get to know each other a little more. We talked for hours upon hours so much as my roommate thought I got kidnapped! After leaving the second bar, Tony offered to take me home and since he checked all my boxes, I agreed. We hopped in the car, to which Tony opened the door, and headed to my place. Tony is pretty reserved and I wasn’t sure if he was going to kiss me on the first date so being the modern woman that I am, I took matters into my own hands and kissed him on the cheek at a stop light and beat him to the punch!.

From there we had an eventful summer of eating out, going to festivals, and watching football games. We found ourselves spending more and more time with each other week after week. After months of dating, we made things official on our trip to Puerto Rico and haven’t looked back since!

How He Asked

I co-write the fashion blog Classic. City. Chic., dedicated to sharing professional style inspiration designed for the office. Like any good SO, Tony is my photographer and usually helps shoot looks on the weekends. So on November 11th, I woke up early that morning, planned my looks, and got dressed while casually being told to ‘hurry up’. I wasn’t in much of a rush and it was cold that day too so I wasn’t so sure why Tony was so excited to shoot photos that day! I honestly thought he wanted to get back to watch the college football games!

We headed to Merchandise Mart and when we arrived, Tony looks at me and says he has a surprise! My heart stopped for a second and I asked what it was and to my delight, Tony hired a photographer to take my photos as an early birthday gift. I rarely shoot with a trained photographer so normally I just direct Tony and we try a few different angles and go from there. This was definitely a treat to work with someone who knows how to use angles and lighting. Plus, Tony got to sit back and relax for once!

After shooting a few looks, we moved to the Wells St. bridge which is my favorite view of Chicago. Ian (our photographer) instructed me to face the river so he could get me looking out into the city. As I’m looking outward, with my back turned, I hear footsteps and I thought “That’s a weird sound for a car”, thinking it was a car going over the bridge.

Engagement Proposal Ideas in In our hometown of Chicago!

To my surprise, as I turned around I see Tony down on one knee with a ring in hand. I started crying immediately (cue the ugly cry photos!) and kept saying “Oh my gosh!” over and over. I gave him a huge hug and kiss and he said “I’m not done yet!” We laughed a little then he continued to share his feelings with me and asking “Will you marry me?”, to which my reply was, “Of course”.

I immediately called my parents and headed to their house for breakfast to celebrate.

Sydney and Anthony (Tony)'s Engagement in In our hometown of Chicago!

Sydney's Proposal in In our hometown of Chicago!

Special Thanks

Ian Vecchiotti
Photographer
Sean Slevin | 
Ring