Two Chicagoans walked into a bar… well, not quite! They 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, Sydney was swiping across Tinder and noticed a tall, bearded, gentleman with a sweet smile who quickly caught her attention. Sydney scrolled through his photos consisting of friends, family and food and optioned to swipe right and to her delight, they matched! They chatted back and forth learning about each others interests, work out regimens, travels, and Netflix binges for two full weeks before meeting in person. They had their first date at Big Star, a delicious taco spot in Wicker Park, followed by a round of drinks at a bar to close out their evening filled with non-stop talking from Sydney and Tony listening with delight. (Duh!) Offering to take her home, they hopped in the car (of which Tony opened the door) and headed to her place. On the way there, Sydney leaned over and gave him a kiss and beat him to the punch! From there they had an eventful summer and found ourselves spending more and more time with each other week after week. After months of dating, they made things official on their trip to Puerto Rico and haven’t looked back since!

As the co-founder and writer of the professional style blog, Classic. City. Chic., Sydney woke up on Saturday, November 11th, planning to head downtown for a normal Saturday shoot with Tony as her go-to, amateur photographer. Tony had a surprise up his sleeve. Once they arrived to the shoot location at Merchandise Mart, Tony turns to her and says he has a hired an actual photographer the time around for an early birthday gift. After shooting a few looks, they move to the Wells St. bridge, her favorite view of her hometown, over the river. On the last shot, and with her back turned, she turned around and to her surprise sees Tony down "on bended knee" with a ring in hand. Sydney tears up immediately (cue the ugly cry photos) as Tony smiles up at her waiting to pop the question. Eager to to say "Yes!" Sydney immediately hugs Tony and while he says “I’m not done yet!” and proceeds to tell her his most private feelings. After more tears, Sydney replies not Yes, but "Of course"! After an emotional morning, they called their family and close friends to share the news and enjoy this moment together.