Mark and Cheryline

Mark and Cheryline's Engagement in New York, NY

How We Met

Cheryline: Mark and I met early on in Dental School, briefly at a mixer the school was throwing. the interaction was brief, and we both made our assumptions about each other based on the quick interaction-him thinking I was a stereotypical Jersey Girl (i’m not from Jersey), and me thinking he was a stereotypical meek Asian boy.

After that we didn’t have much interaction, until the next year when we were placed in several small group classes together. I began to notice things about Mark that I liked: he was really well mannered, he had good taste in clothing and a seemingly cute sense of humor, and he even prayed before he ate – which I found adorable. I was in a long term relationship at the time so my intentions with Mark were always just friendly. After spending more time with Mark in class, I began to tell my other friends how I couldn’t believe we had so much in common and how I felt like Mark was going to be my new “best friend.” They thought I was crazy, but in typical “me” fashion, I more aggressively began to impose myself upon Mark, asking him to study with me, get coffee breaks with me, and later on even go work out with me. Mark, being the respectable gentleman he always is, just went along with everything cautiously since my boyfriend at the time didn’t seem to mind our friendship. From then on, we were pretty much inseparable in school and otherwise, but with the constant lines of appropriateness being toyed with but never crossed. I began to worry that Mark might be the perfect guy for me that I was letting slip by. I remained loyal to my boyfriend at the time, but always just existed with feelings of guilt, fear and sadness that I might be messing up my life by doing so.

Long story short, after FOUR YEARS of this tortuous “best friend” game we played, fate stepped in and my past relationship ended. Despite my feelings of failure and cowardice, Mark loved me just the same and we finally began seeing each other months later. Sometimes things are taken out of your own hands for the better, and I owe everything to God or fate or whatever force one might believe in for interceding and finally connecting me with my soul mate, who was in front of my face all along.

How He Asked

Mark: Cheryline is an obsessive planner – she was already thinking about the details of our future wedding before I had even proposed. She’s also insanely clever and always brags that she can never be surprised because she always figures it out beforehand. So I knew when it came time to propose, I had my work cut out for me.

I always knew that Cheryline wanted something truly personal to us for our proposal – nothing generic. When we were in dental school, we used to spend hours at my apartment studying, hanging out, getting to know each other – and eventually becoming “us”. Even though she had a boyfriend at the time, the time we spent there shaped us and it was where we formed the bond that became our eventual relationship. Because of that, I knew that I wanted to incorporate the apartment into the proposal. I thought I could bring her back to the apartment and have it decorated and propose to her there.

Just one problem – I don’t live there anymore!

So how do I get access to the apartment? I tried asking the lady I used to rent from – and she loved the idea! But after she got me in touch with the current tenant, he responded to my idea with a simple “I’m not comfortable with this – good luck”.

Next, I got in touch with the building management, but they said that because each apartment is individually owned, they couldn’t give me access to any apartment.

Finally, as a last act of desperation, I reached out to every single realtor who had a listing online for apartments in the building. I sent about 15 e-mails to random realtors explaining what the apartment meant to us and how I wanted to propose there. Of those 15, 14 people said no.

Lucky for me, 1 said yes!

Turned out, the owner was an NYU alumni and her husband went to NYU dental. She loved the story and felt like she had to help us out. And the apartment had the exact same view and set up as my old apartment did.

I set up with a few friends at the apartment the night before the proposal. We decorated the place with lights and flowers and mapped out the proposal night perfectly. On the night of, Cheryline met me in the city to go out to dinner with some friends, We got to the restaurant and all my friends were “late” (they were actually in the apartment doing final preparations). When she started ranting about how my friends are always late, I suggested we take a walk until they arrived. The restaurant I chose happened to be right across the street from the old apartment.

I pointed at the apartment and reminisced about how much time we spent at that place and she mentioned how much she missed it. I told her we should walk by the apartment. But when we got to the entrance, I stopped short and asked her if she trusted me. When she confusedly said yes, I took out a blindfold and brought her upstairs. When we got upstairs, the room was all lit up with one of our favorite songs blaring through the speaker. I brought her into the room, told her how much I loved her, got down on one knee, and she said yes! And the best part was I surprised the girl who swears she can’t be surprised.

Where to Propose in New York, NY

Proposal Ideas New York, NY

After my friends popped out to add on to the surprise and sip some champagne, I told her we had to rush home to share the good news with our families. What she didn’t know is that I actually had our families and friends gathered as well for an impromptu engagement party. She walked in thinking she was gonna be surprising everyone with the good news, but instead she was the one who got surprised for a second time that night.

It took every bit of effort from me to surprise her, and I’m pretty proud of myself of pulling it off. More important, I’m so excited for us to start the rest of our lives together.

Our Video

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Special Thanks

Roderick Rubi | 
Videographer