I love telling the story of my proposal. I was completely surprised that day when he proposed! However, I was not surprised THAT he proposed – we had lightly discussed wedding plans and our long-term vision for our relationship. 

I was surprised by my proposal… not shocked. 

My fiancé proposed on July 22, 2021 in The Liberty Hotel in Boston. I had been anticipating a proposal, but we had been in Punta Cana literally two weeks previously and I returned ring-less. Since we had an upcoming trip to Ukraine in September, I assumed he would propose during that trip.

However, I was talking with one of my friends, and she informed me that “if you think he’s going to propose, you need to ALWAYS have your nails done” – I am grateful for her words of wisdom. 

A key thing about my proposal story is I literally had NO idea it would be that day. All the hints throughout the story are completely in hindsight. Trust me, I was completely shocked. 

While the story is now “My Proposal,” I will tell the story as “My Random Thursday In July”:

Back Story: My boyfriend had purchased two tickets for a Champagne Dinner, Featuring Tattinger, at the Clink – the swanky cocktail bar in The Liberty. My boyfriend loves fancy dinners, especially if they involve wine pairing and dressing up. A few days prior, he told me he found tickets to a private pre-party to meet the chef. My fiancé not only invests in restaurants, but also ALWAYS upgrades events if there’s an option, so I was not suspicious. I was looking forward to a typical (albeit fancy) evening out with him. 

6:00 AM –  I am rudely awoken by absolute demon cramps. I proceed to experience what can only be described as an exorcism for the next hour, with my beloved offering me advil (which I cannot keep down) and heat pads. I cancel my personal training session and spend the next 4 hours in bed.

10:00 AM – I am making a shaky recovery, finally able to keep down some advil. My then-boyfriend pokes his head into the bedroom and suggests that even if we cannot make the Champagne dinner, we should at least go to the pre-party. I shoo him away and tell him I’ll make it to the whole event. 

1:30 PM – My fiance is gathering his things to leave for work, and gently informs me the event will be very nice and suggests I get my hair done. I snap back at him that I literally have a hair appointment in the calendar. He pushes a bit further and says “just make sure you dress up” to which I sarcastically retort “uuuhhh, I’m actually going to wear sweatpants!” (I don’t even own sweatpants). He heads to work looking nervous.

2:00 PM – I get my hair done and humble brag to my hairstylist about how lucky I am that my boyfriend brings me to fancy events. I truly am blessed.

4:00 PM – I’m finishing getting ready for our event. My then-boyfriend keeps looking at me funny – in hindsight it was with love, but at the time I was annoyed. I confrontationally question him, “Do I look ok? Should I wear the pearls? What?” and he gently responds “Yes, the pearls would be nice.” Now…. He never really weighs in on my outfits, so I decide to listen, and I wear the pearls he got me for Christmas. 

4:15 PM – We’re heading out the door, and I am about to opt for a pair of beige flats. I had a recent knee surgery, so heels can be quite difficult for me. As my fiancé is pulling on his dress shoes, I appreciate how nicely he has dressed up. I decide to wear my Steve Madden wedges to match his energy a little better. 

4:50 PM – We arrive at The Liberty after I whined about the traffic the entire drive there. As we enter the building, I surreptitiously remove my Fitbit so I don’t look like a spy-kid. 

4:55 PM – The concierge greets us by name, and then grandly says “Let me bring you to the private party”… wow, ok, this is fancy and I’m glad I dressed up.

4:56 PM – The concierge takes us to the room section of the hotel, and we ride up the elevator. I was starting to get nervous… this must be quite a fancy event. I’ve never been to a private party in a hotel room. I feel so nervous/excited/confused/impressed/EVERYTHING

4:58 PM – What was the last thing you said to your husband right before you got engaged? For most women, it’s something conversational or random… like “this hike is kind of long” or “oh, is your shoe untied?” Well, I WOULD have said “oooo my fancy man taking me to fancy places oooooo” BUT the concierge was right there…. and I wanted him to think I was a cool metropolitan woman who regularly went to private hotel room parties. So, I just stayed quiet

4:59 PM – We are led right up to the suite, and the concierge opens the door. There are candles and rose petals ALL over the suite. It’s stunning. 

4:59 PM – My dumbass still thinks this is an event, so I’m quite confused. It feels… romantic? What? Is the chef a pervert? What is going on? No longer cool with this party. 

4:59 PM – My man leads me through the living room of the suite and into the bedroom, I see something in there, and time slows down. 

5:00 PM – On the bed in rose petals it is written “Will you marry me?” but I only see my fiancé. I don’t remember much from that moment, all I saw was his face – I didn’t even see the ring! He is on one knee, and proposes to me. I scream (or so I am told, I don’t remember) and jumped into his arms. Yes!

5:01 PM – I scream a second time as the photographer scares the living daylights out of me. There was A WHOLE MAN IN THE ROOM AND I DIDN’T EVEN NOTICE!!!  

A little after 5 PM – I am still quite disoriented but I finally notice the ring. It’s gorgeous and fits perfectly. My fiancé has this look of relief on his face, and I feel absolutely ecstatic. I had somehow lost my purse in the room, but I’m not even worried. We take more photos with the photographer around the hotel. 

6-ish PM – My fiancé had made up the pre-party, but we were actually signed up for a Champagne dinner so we attend! I don’t have any photos from the rest of the night because I left my phone in my purse up in the room. 

??? PM – We finally retire from dinner and return to the room. My phone is dead, but I figure I can just update everyone tomorrow. It was such a magical night and I feel so surprised, happy, and lucky to be with such an amazing man.