Our Engagement Story

by | Nov 1, 2018 | life, life changes | 4 comments

Who doesn’t love a good engagement story, am I right? Three years ago today, Adam proposed to me. I still remember that day like it was yesterday. Isn’t it crazy how some memories are so vivid? Anyways, in celebration of our engagement-versary, I thought Adam and I would recount how that day went for the both of us…

Kelly and Adam smile happily after the proposal.


I had totally been one of those girlfriends. The girlfriend that kept pestering her boyfriend when they were going to get engaged. After all, I had a plan all mapped out for my life: what year I wanted to get engaged, what year I wanted to get married and so forth. I knew a proposal was all about the element of surprise, but not knowing when Adam was going to do it drove me nuts!

Every time there was a big event happening, I thought Adam was going to propose. Weeks turned to months of holidays, birthdays, milestone events and I was getting anxious. In mid-October 2015, knowing that I like to plan my weekends far in advance, Adam asked me if I was free on Sunday, November 1st to have dinner with his co-worker and his new girlfriend. I was, so we made the plans and I marked it on my calendar.

The day before, Adam let me know we were going to dinner in Lincoln Park and that we should “probably dress a little nice” because his co-worker, Kevin, dresses really nice. Okay, I thought.

That Sunday morning, November 1st, I decided to go shopping. My nail polish was chipping so I figured I’d go get my nails done that day too. Well, turns out I shopped too long and didn’t have time to get my nails done because Adam said we were leaving our apartment at 3pm. 3pm!? For dinner!? I didn’t understand. But, Adam said he wanted to walk around Lincoln Park with Kevin and his girlfriend before dinner since it was such a nice day. It really was – it was mid-60s and sunny – the perfect fall day.

I thought it was a little suspicious so I started texting my family and closest friends. I was like, “Is this the day!?” Then I started getting frantic because I didn’t know what to wear. I asked Adam what I should wear and asked if I could wear jeans and he said no. I was so sad because those are my staple! I nervously started looking for another outfit that would look nice. Once I picked it out and figured it would do, I looked down at my nails. The horror! I wanted to make sure they looked good – just in case. I quickly painted them myself right before we left.

As my nails were drying in our Uber, I asked Adam where we were meeting Kevin. He said we were going to head to the lily pond in Lincoln Park. I thought that was a strange location to meet so my heart started to flutter. Maybe today is really the day, I thought. But then I started second-guessing everything and told myself not to get my hopes up (like I had every other time). My family and friends were blowing up my phone and Adam was busy texting Kevin (or so I thought).

Once we got to the Alfred Caldwell Lily Pond, Adam said that Kevin was running late so we should go inside and just walk around instead of waiting outside. I thought it was a little weird, but I went along with it. As we were walking, Adam led me down a few steps near the pond and told me to take my sunglasses off. Well, I never take my sunglasses off when it’s sunny so I immediately asked why I needed to. He told me just to do it and that’s when I knew.

Adam on his knee and proposing to Kelly.

He said everything I had always hoped he would say and got down on his knee and pulled the ring out of his sock! He asked me to marry him and I said yes. At that moment, I noticed a photographer across the pond snapping pictures and asked Adam if he hired someone. He told me yes, which shocked me the most since he told me he’d never do that! I was so happy to have that special moment captured. We spent the next hour taking pictures and then we called all of our family and closest friends. It really was the most perfect day.

Kelly and Adam sit on rocks smiling.


I had known for a long time the exact spot where I wanted to propose to Kelly. We had visited the Alfred Caldwell Lily Pond at Lincoln Park in Chicago numerous times. Every time we went, I always said to myself that it would be the spot. I had always wanted to throw Kelly off by suggesting I wouldn’t do the proposal in public or ever get a photographer and made her think it would be inside our condo.

Alfred Caldwell Lily Pond in Lincoln Park.

Unbeknownst to Kelly, I had secretly arranged to have a photographer to shoot the big moment when I got down on one knee and then take some photos of us in celebration mode. About a week before the big day, I scoped out different spots at the lily pond, keeping in mind it had to be a good vantage point for the photographer. I found the perfect spot and prayed no one would be in that exact spot when we arrived on the big day.

I told Kelly we would be going out with my coworker Kevin and his girlfriend for dinner in Lincoln Park. I figured we could either go to the park in the morning/early afternoon before dinner in our workout gear or right before dinner all dressed up. Knowing I got a photographer, I erred on the side of caution of having Kelly get a little upset that she wasn’t dressed up for the photos. Timing wasn’t going to be perfect, due to the sun setting so early that late in fall, but whatever, I thought.

That weekend was Halloween weekend and on Halloween, it was around 50 degrees and rainy all day. Kelly always says that I have amazing luck and luck was upon me on November 1st, 2015, the day I was going to ask Kelly to marry me. It was a perfect 65 degree temperature and sunny. Looking back on it now, it really was the last nice day in the fall for Chicago.

Since the sun was setting that day a little bit after 4:30 pm, I needed to get there at 3pm. Typical Kelly was running really late and I couldn’t act too unusual to ask her to hurry up without being too suspicious. In the taxi, I definitely had some butterflies in my stomach. I also mischievously put the photographer, Tracy, as my co-worker Kevin in my phone in case Kelly asked who I was madly texting on the way ha!

We ended up getting to the lily pond about 25 minutes late. Whoops. I called Tracy, disguised as Kevin, and she was all set. We walked to the spot and there was a couple sitting 15 feet away from the designated spot I so carefully chose, but I said to myself “eh, screw it, here goes nothing.” I got down on one knee and asked my best friend to marry me.

Kelly and Adam hold hands, showcasing her engagement ring.

She said yes (of course)! She was hugging me and crying when she noticed Tracy taking photos out of the corner of her eye and laughing said “you got a photographer?!” thus earning me a lifetime of brownie points 🙂

Kelly crying after being proposed to.

We called her parents first, even though they knew I was going to ask her. I had asked for their permission a couple weeks beforehand. Then, we surprised my parents with the big news. I took Kelly out to celebrate for dinner afterward where we had a proper celebration. What a great day! Pink lipstick stain


Welcome to Lipstick & Ink®, your home for everything career and wellness inspired. I’m Kelly, a Chicago-based career coach, writer, speaker, and events host.

Whether we’re working together on your career aspirations, refreshing your professional documents, or keeping your mental health in check, I encourage you to own your power and make your mark.




  1. How I so remember that day. Good thing you did your nails before you left. Kudos to Adam for a wonderful proposal.

    • You got that right! He did a great job with the proposal!

  2. Nothing like getting teary-eyed on this beautiful December 1st morning! 🙂 Still so incredibly happy for the two of you and cannot wait to see what you accomplish together in the years to come!

    • Aww, Jenna!! Thank you so much! So appreciate the kind words 🙂


Submit a Comment

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.