Our Engagement: How He Proposed
Hi friends!
Guess what? I’m officially ENGAGED! Yes, Jon finally popped the question, and I said yes without hesitation. But this wasn’t just any proposal night. A normal dinner suddenly turned into the most unforgettable moment of my life, and now I’m spilling every detail. If you’re planning a proposal, newly engaged, or just love reading real-life love stories, this one’s for you.
💌 Want all the behind-the-scenes wedding updates, planning tips, and drama I won’t post anywhere else? Sign up for the newsletter, I spill everything. → Join the list here
A Magical Moment: The Proposal
When we arrived at the restaurant, a group of our friends and family greeted us. I was so confused and wondered why they were all there. Then Jon got down on one knee and asked me to marry him! I was over the moon and couldn’t believe what was happening. It was the most magical moment of my life!
Thinking back, there were some clues that Jon was up to something. He had bought me a beautiful dress to wear that night, but I thought he’d propose many times over the years, much to my former disappointment, lol, that I convinced myself not to get my hopes up. But Jon had other plans, and I’m glad he did!
My engagement ring is a marquise-cut diamond with a diamond band, and it’s everything I ever wished for. Jon knows me well. He picked a ring that perfectly suits my style! Plus, it was on the vision board in our bedroom for like four years, lol.
I was still in shock, so I barely did anything but blink during dinner, but so grateful to have everyone there to share our joy. When we got home, I shared the news online, and the outpouring of support was overwhelming. It’s amazing how much love you get when something like this happens.
Now that we're engaged, we’re starting to think about the wedding. I already have a list of potential dates, sorted by aesthetics, predicted weather, and numerology… yes, I’m that girl... LOL. We haven’t decided anything yet, but I want a peaceful, light, airy, glamorous, stress-free, and fun day.
I'm so excited to start this new chapter of my life with Jon, and I can't wait to share all the exciting moments with you along the way! I'm still trying to wrap my head around all the wedding planning ahead!
Planning Our Dream Wedding
I’m pretty traditional, so I’m sure many traditions will make it into the big day. Honestly, I like to do things myself because other people tend to stress me out. But wedding planning is no joke, so I’ll need help, especially from Jon.
We haven’t picked our wedding party yet, but we have a good idea who to ask. I can’t wait for all the pre-wedding celebrations, engagement party, bridal shower, bachelor/bachelorette, and rehearsal dinner. I want each event to be just as special.
The venue is still up in the air, but there’s one place in Lenox, MA, I love. Probably out of budget, but a girl can dream, right? I’m a checklist queen, ready to tackle wedding planning head-on. Jon’s excited to be involved, which feels amazing.
We both love the idea of a romantic glam vibe for the wedding. I have a clear vision for my dream dress and want Jon to wear a classic tux, but I’m still figuring out the attire for the wedding party.
My biggest fear? Dealing with difficult people. Weddings bring out the worst sometimes. Anyone invited needs to leave negativity, stress, and drama at the door. After eight years of us against the world, nothing will ruin our day. Don’t make me be a Bridezilla. If someone messes with us, they’ll see a side of me they’ve never met.
Overall, I’m excited, nervous, and a little overwhelmed. But with Jon by my side, this day will be everything we dreamed of and more.
👰🏻 Wedding planning checklist coming soon, it’s Type-A Barbie certified. Want early access before it drops?
Get on the waitlist 💍
Navigating Traditions and Challenges
It’s been quite a journey, but I’m still in shock. I can’t believe I’m engaged to the man of my dreams after almost eight years. We’re over the moon and celebrating non-stop. It’s been overwhelming in the best way.
Wedding planning is on our minds. We decided on an engagement party, but are still debating the venue: fancy place or at home with close friends and family. Tough call, but we’ll figure it out.
I asked Jon why he wanted to be with me forever, besides, you know, what a great catch I am, lol. He said we’re a perfectly balanced team. Our strengths and weaknesses are mostly opposites, and that’s how he knew he wanted forever with me. We push each other to grow and are there when the other falls. It makes me feel so secure.
It hasn’t been easy. We had fights over the years, but we grew through them. We started dating when I was 18 and he was 21, navigating the ups and downs of growing up together. Worth every stupid fight that every long-term couple knows.
Jon was so nervous proposing, he almost forgot what to say. He’d planned the proposal over a month out at one of my favorite restaurants, but two days before, they canceled the reservation due to expected busyness. Jon scrambled to rebook since my mom was leaving the next day, and our friends had already cleared their calendars.
Thankfully, Sorelle, an Italian restaurant in my hometown, came to the rescue. The staff treated us like royalty; the room they set up was gorgeous, and the food was fantastic. It made me sad to lose the original spot since I loved it and recommended it to everyone. Now, I don’t think we’ll return.
As a business owner, I get it, but if it were my business, I’d roll out the red carpet for someone planning to propose. I know guests celebrate more on those nights, a 20+ top reservations in a small restaurant would be a dream. To each their own, I guess. The owners and team at Sorelle were angels who made our night perfect. I’m beyond grateful and now have a new spot to celebrate special occasions.
I'm so excited to plan the wedding, and I can't wait to see what the future holds for Jon and me. I feel like everything is finally falling into place, and I'm so grateful for it all. I'm also excited to share this journey with all of you and keep you updated along the way.
I’m so excited to plan the wedding and share this journey with you. I still can’t believe I get to spend my life with Jon. We’ve grown so much and are just getting started. Whatever comes our way, we’ll face it together. Life is funny like that, and I feel so lucky.
🔒 EXCLUSIVE: My Full Wedding Vision Board (Dress Inspo, Color Scheme, + Ceremony Vibes)
Our Journey: Strength, Love, and Resilience
Jon and I have been together nearly eight years, and honestly, he’s the best thing that ever happened to me.
We met in 2016 and hit it off right away. I felt comfortable like I’d known him forever, something I’d never experienced before.
A few months in, Jon told me he wanted to get married someday. At 18, I wasn’t thinking about that, but hearing it made me happy.
Fast forward to 2018, and my world was turned upside down when my dad was diagnosed with stage 4 colon cancer. It was a tough time for me and my family, but Jon was there for me every step of the way. He did everything he could to help my dad and make sure that we were all okay.
During this time, Jon even asked my dad for his blessing to propose to me. I had no idea then, but my mom later told me about it in her speech at our proposal. She said my dad was so happy for us, giving Jon his blessing without hesitation. It meant the world to me that my dad got to be a part of our story like that.
After my dad passed away in 2020, I fell into a deep depression. I didn't know how to cope with the loss, and it felt like everything was falling apart. It was a really tough time for Jon and me, but he never gave up on me. He was my rock and my support system, and I don't think I would have made it through without him.
After a lot of therapy and hard work, I finally started to heal, and our relationship grew even stronger. Jon proposed to me two days after his 30th birthday, which was the happiest moment of my life. I knew without a doubt that I wanted to spend the rest of my life with him.
Now, we're planning our wedding and couldn't be more excited. Jon hopes that the day can be summed up in one word: peace. We both want it to be a day where we can celebrate our love and honor my dad's memory in a meaningful way. As for traditions, we have yet to really think about it. We're both pretty laid back and just want to have fun with it. I want something traditional but not too long or complicated for the ceremony. I'm still figuring out which traditions I want to incorporate, but I'm considering adding some Catholic ones, even though I don't formally practice anymore, or some from my Italian heritage.
Jon loves calling me his fiancée now, so I know he'll love calling me his wife even more. I feel so lucky to have found someone like Jon, and I can't wait to spend the rest of my life with him. He's my best friend, partner, and soulmate, and I know we'll be able to conquer anything life throws our way.
Looking Ahead: Excitement and Commitment
Now that Jon and I are engaged, it's been an incredible journey, and I'm so grateful for the love and support we've received from our family and friends.
I have to admit, since Jon popped the question, I have felt calmer and more at peace. It's like we've taken an enormous step forward in our relationship, and I just know that we're meant to be together. Jon feels the same way. His biggest advice for anyone planning a proposal? If you're planning to do it at a venue, get it in writing!
Looking ahead, Jon and I are both so excited about the next five years. We can't wait to get married and start building a more established life together. And being engaged brings such a sense of security to our relationship. It's like we're both fully committed to each other, and that's an amazing feeling.
One thing Jon and I both believe in is staying true to our commitments. He's so happy about the commitments he's made to me. Before the wedding, we're just looking forward to getting closer and closer. We want to ensure we're on the same page about everything and fully prepared for the next chapter of our lives together.
Marriage has a time-tested value, and we both believe in its importance. For Jon, it was especially important to show me how much he loves me and that choosing each other was the right decision. And honestly, everything is just so exciting right now! We're both so happy and in love, and we can't wait to see what the future holds for us.
Thanks for taking the time to read about our engagement journey. It's been a whirlwind, but we're so grateful for every moment of it. And to anyone still waiting for their special someone, remember that love takes time. Trust in the process, and don't be afraid to take a chance on love. You never know where it might lead you.
💍 Proposal FAQs: Everything You’re Secretly Googling
How do you plan a stress-free engagement party?
Short answer: boundaries and batch planning. Whether you go big or keep it cozy at home, know what you want the vibe to be. I recommend choosing 1–2 people to help, setting a clear guest list early, and prepping food and decor ahead of time so you're not spiraling the night before. I’ll be sharing my party checklist soon. Get on the newsletter list if you want first dibs.
What’s the best engagement ring cut for long fingers?
If you have longer fingers like I do, marquise-cut diamonds are super flattering. They elongate the hand even more and feel timeless but still unexpected. My ring is a marquise diamond with a diamond band, and it’s the exact one I had on my vision board for years.
How do I know I’m ready to get engaged after dating for years?
Jon and I were together for 7 years before getting engaged. There’s no perfect timeline, but when you feel peace about forever, that’s your answer. If your relationship has weathered storms, grown through hard things, and you still want to choose each other daily, you’re probably ready.
What are low-key wedding planning tips for Type-A brides?
Make a master checklist with every task, but highlight just 3 things per week. Outsource what stresses you out, and don’t let people pressure you to do things “their way.” I’m making a Chronically Chic Wedding Planning Checklist that’s Type-A Barbie certified. Sign up for the waitlist if that’s your vibe.
How do you honor a parent who passed away during your wedding?
My dad passed away in 2020, so this is something I’ve thought about a lot. I’m planning to include him through subtle, meaningful touches, maybe a charm on my bouquet, a candle, or even playing one of his favorite songs during dinner. You don’t have to make it a public moment if that’s not your style. It’s okay for grief and joy to live side by side.
What’s the most common proposal planning mistake?
Not confirming your reservation in writing. Jon’s original proposal venue canceled two days before, it almost derailed everything. If you're planning to propose at a venue, get the date in writing, confirm the time, and double-check everything. Your future self will thank you.
Is it normal to feel overwhelmed after getting engaged?
YES. I was excited, but also weirdly in shock for weeks. I could barely eat dinner the night he proposed. It’s a big emotional shift, don’t feel bad if you’re not immediately Pinterest-board obsessed. Let the feelings settle. It’s okay to take your time. I’m still not even really started lol.
How do you decide on a wedding vibe if you like multiple styles?
Create a vision board that blends them, mine includes romantic glam with peaceful, airy, light-filled aesthetics. I also narrowed down by what would feel the most like us, not just what looks cute on Instagram. If you're torn between styles, ask yourself: which one would still feel beautiful to you in 20 years?
What’s a good timeline for wedding planning after getting engaged?
It depends on your budget, guest count, and venue flexibility. Some people plan in 3 months, others take 2 years. We’re still figuring ours out, but I started by locking in our non-negotiables: season, vibe, and venue. (which is where we are stuck, our ideal venue seems to be a unicorn… Start with the big rocks, then build around that.
💌 Want the inside scoop as we plan the wedding of our dreams?
I’ll be sharing exclusive updates, planning wins (and fails), plus every glam detail in my newsletter. → Sign up here and come along for the ride!
💍 Already engaged? What’s been your fave part so far? Drop a comment or DM me on Instagram, I wanna hear your story too.
💕 Planning a wedding? You’ll love my Chronically Chic embroidered socks they’re perfect for bachelorette sleepovers, getting ready morning-of, or cozy honeymoon nights.
