Kylie and Ilir

Proposal Photography + Engagement Photography | How He Asked: My Proposal Story

How We Met

Our story didn’t start in the most romantic of places… instead, it began in a sweaty high school weight room filled with overly confident, incredibly awkward high school kids. But one of those kids caught my eye. Ilir was a junior and there for basketball and I was a freshman and there for cross country. We bumped into each other in the back corner, but in true high schooler fashion, we didn’t say a word. That night, I, of course, used my sleuthing skills to check out who this kid was on Facebook… and feeling bold at the time, I sent him a Facebook request.

A couple of days later we bumped into each other again in the weight room and Ilir comes up to me. “Hey, are you the girl you friend requested me on Facebook?” Smooth Ilir. “Oh, I don’t know!” Oh, I knew. And that’s where it all began.

Engagement Photos + Surprise Engagement Story

We talked on and off throughout Ilir’s next year and a half of high school, but of course, discovered our spark as Ilir was heading off to college. The night before he left, I was wearing his sweatshirt and when I tried to give it back, he told me to keep it so he’d have to see me again soon. Slightly smoother than his weight room pick-up line.

Not knowing what would come from it, we continued talking and seven years later, we still haven’t stopped.

How He Asked | Chicago Proposal

Across different schools and different states, we held on tight to what we knew would be something special. We attended different colleges, began careers in different states, and have taken plenty of plane and train trips across hundreds of miles. From Illinois to South Carolina, our love has been strengthened by the distance in between us for seven years.

He is the perfect balance for me. I am fiercely loyal, incredibly passionate, and I love with all my heart. Ilir is calming, kind, mature and will do anything to see others happy. I am a planner and a timeline-creator, and Ilir is spontaneous and adventurous. I drive him crazy and he drives me crazy, but we love each other more than words can say.

How He Asked: The Perfect Proposal

How They Asked

I think I might just have butterflies for the rest of my life. June 8th, 2019 was absolutely perfect and everything I could have ever hoped for. My best friend got down on one knee in the middle of a real-life fairytale he created just for me – and now, I get to spend the rest of my life with him.

Ilir so sweetly follows bloggers, creatives, and photographers I love because he knows how interested I am in creating beautiful things, and how much I admire others who do this so well. The love he has for seeing the passion in other peoples’ eyes is one of my favorite parts about him. He will often send posts with location inspiration or blog posts ideas, and one day, he sent me an Instagram story from one of my favorite photographers, Alicia, also known as Aesthetiica in the blogging world. I have been in love with her work for such a long time and admire her creativity tremendously! Alicia posted a casting call and was looking for couples to shoot. What a DREAM. Minutes after Ilir sent it to me, I was in Alicia’s inbox.

Wedding Proposal Ideas in Chicago, IL

Kylie and Ilir's Engagement in Chicago, IL

I truly thought there was no way she would pick us, knowing how many responses I was sure she would get. When she said she was interested in shooting with us, I was ecstatic! Little did I know, this was all a setup.

After work, I went out and bought a new outfit, came home and did my nails (thank goodness), threw some self-tanner on, did a face mask, and got ready for an exciting shoot the next day. Of course, every girl prays they have their nails done and are in a cute outfit when a proposal happens, so this was such a clever way to make sure I was prepared without risking me catching on.

Proposal Ideas Chicago, IL

Marriage Proposal Ideas in Chicago, IL

Ilir woke up early Saturday morning and promised me he would not cut it close for our big day (for me, the photoshoot; for him, a proposal… little did I know). He got to my apartment early and I made us some breakfast and popped some bubbly. I was so nervous to be shooting with Alicia I told Ilir we needed a little mimosa before we went – ha!

We headed towards the location Alicia sent to me and Ilir played it pretty cool, considering we were heading to the spot he chose. (Later on, he told me he spent hours driving around Lincoln Park, my favorite Chicago neighborhood, trying to find the perfect location. So sweet!). He acted just as he normally does when we are trying to get somewhere – I can’t figure out a map to save my life and so he grabs the phone and leads us there. Ha – typical! He walked us over to what will be “our spot” for the rest of our lives, we found Alicia, and he introduced himself like he hadn’t been talking to her for the past four months…

Where to Propose in Chicago, IL

The location was absolutely gorgeous. There were the Chicago skyline and the lake in the background and the beautiful flowering trees all around us. The weather was a perfect 75 degrees and sunny and it was absolutely amazing.

We started off doing some “warm up” pictures where Alicia had us walking and talking, holding hands and doing coupley things. Ilir told me later on, this was her strategy to find the picture spot with the best lighting for Ilir to ask the big question. Such a perfect plan! Next, Alicia asked us to stand back to back. It seemed a bit strange, but I fully trusted the master at work. I knew she knew what she was doing, so when she told us to close our eyes and hold hands, I didn’t even question her. I was standing there thinking about how silly it felt and how much confidence I had that it somehow was going to look great. When she told Ilir to take a couple of steps forward, I didn’t think twice.

Then, she told me to turn around.

Proposal Photography + Engagement Photography | How He Asked: My Proposal Story

I glanced back and saw Ilir down on one knee and I can tell you so honestly, it really didn’t hit me. Not for a couple of seconds. If you watch the video down below, I think you can see the exact moment it really hits me. You know how sometimes when you are in complete shock, your mind takes you to illogical places for a second before you figure out what’s going on? I know this makes no sense whatsoever, but as I entered my moment of pure surprise, for a split second I thought maybe Alicia just needed some pretend engagement pictures. So I giggled a little but then looked into Ilir’s hands and saw the ring – and it was my ring. It was the exact ring I had told Ilir I wanted when he asked me to start thinking about what kind of ring I would want one day, but even better. Then, Ilir started talking. In all honesty, I really don’t know what he said, outside of “will you marry me?” (Later that night I asked him to repeat his proposal because I couldn’t process any of it at the moment – I was so overwhelmed with emotions I couldn’t even think! Of course, the second time around, I gushed over it. Everything he said was perfect).

Without a doubt, I said yes! I’ve never been so surprised in my whole life, but also so certain in my answer.

Oval Solitaire Engagement Ring | Engagement Stories | How He Asked

The Perfect Proposal + My Engagement Story

I laugh looking back at the video and the pictures because while everything Ilir planned was perfect, my reaction leaned much more heavily on authentic awkwardness than perfection. I didn’t even hug him for a solid minute after he PROPOSED. I just stood there trying to wrap my mind around what just happened! HA! But I guess that’s what made the moment so much more real.

Alicia and her assistant Jess let us have our moment and then began laughing with us, saying “this was all for you!” There was no model call. The conversations leading up were all pretend. Ilir crafted the most perfect plan and I was TRULY surprised.

Proposal Photography + Engagement Photography | How He Asked: My Proposal Story

We started to shoot a few more pictures right after the big moment while shock was still running through me, and then it started to sink in bit by bit. I turned to Ilir, started crying, and my first question was, “did you talk to my parents?” When he told me he asked them a year ago, oh goodness, that hit me. I started asking so many more questions like “why now?” I am a type A person who follows timelines and makes plans, but Ilir’s response was simply filled with pure love and a strong passion to call me his fiancé. (Another place where he balances me so well.)

I paused on all of the other questions that were running through my mind and just let the moment soak in. We spent another half hour or so shooting and I was on cloud nine. If you know me, you know I LOVE pictures. I want every moment of my life photographed. Most of the pictures I take I don’t even ever show anyone. I just love holding onto memories through pictures, whether it is a casual Sunday night dinner or a lazy Saturday laying in bed. More than anything, I wanted this special moment of my life captured so I could look back at it forever. Not only did he get me a photographer, but he also got me the photographer.

Our engagement pictures encompass all of the fairytale feelings that ran through me during this moment and I will cherish them forever. They are everything I could have hoped for and so much more.

Right after the pictures ended, I asked Ilir when my parents were coming or when we’d see them. He might have gotten me by surprise with the proposal but I KNEW our families would be involved at this moment sooner or later. He tried to throw me off saying he didn’t know when I would be seeing them next, so I pushed him a bit harder, and then he told me we had dinner reservations with them in a few hours. But first, we had some time just to ourselves.

Couples Photography | Engagement Photography | Proposal Photography

After calling family and friends to tell them this exciting news, we headed over to our lunch reservations Ilir booked at one of the newest rooftop patios in the city and had such a special lunch together, up in the sky of my favorite city, sitting in the sun with the 75 degree air breezing by us.

That evening, we joined our family to celebrate the biggest step we’ve ever taken together, and I could not have been happier to see our families as one and so blissfully happy together. To know my parents had known this day was coming for a whole year made my heart melt.

The day was perfect.

I am so overjoyed to have the most incredible fiancé in the world who cares so deeply and lives so lovingly. I truly don’t know what I could have possibly done to deserve such an amazing person as my future husband and I will be thankful for him every single day.

Oval Solitaire Engagement Ring | Surprise Proposal Photography

Special Thanks

Alicia Fierro
Photographer