Jaclyn and Lisa

How We Met

About two years ago, I was in my second year as a family medicine resident in New Jersey. I was overworked, stressed out, exhausted, and definitely not looking for anything serious in the relationship department. At that time sleep was a luxury, so if it hadn’t been my roommate’s birthday weekend, I definitely would have opted to stay home that Friday night. Knowing she would be upset if I didn’t come, I quickly got ready after my shift, chugged a RedBull, and headed to Asbury Park, NJ to meet up with everyone. Once I got there, there was no answer from my roommate and no sign of her or our friends anywhere – I got dressed up, did my makeup, fixed my hair, drank an energy drink that would keep me up for hours and I was all alone and pissed. After what seemed like forever with no luck, I was finally able to get in touch with my other roommate who urged me to stay out since I “never did” with my busy schedule and meet her at a bar called “Porta” for her sister’s birthday. Aggravated and cranky that I sacrificed a night of sleep for a night with likely a bunch of strangers, I made my way there. It was a typical crowded Friday night at “Porta,” with mainly Jersey fist bumping, drunk people in their mid 20’s at every turn, but I quickly found people I knew and the introductions began. One girl caught my eye almost immediately.

Proposal Ideas Two proposals: Hawaii (Tantalus Lookout, Oahu + Haleakala, Maui)

She was wearing white Sperrys, ripped jeans, a button up and had these eyes that just drew me in. My roommate had mentioned her many times as she was a close friend of the family but her description of “a young kinda Asian looking lesbian engineer or something in her early 20’s” didn’t really peak my interest so the two of us had never met. I went up to her and asked if she was the infamous “Lisa” that I had only heard of and she smiled when I introduced myself (melting my heart almost instantly from that smile). Apparently, she had also heard of this “doctor roommate” and thought I must have been made up since we had never met. She had me laughing the whole time and I just wanted to know more about her. She was gorgeous while at the same time being able to pull off a little bit of a tomboy look. I found myself staring at her and couldn’t help but smile. She was beautiful, intriguing, funny, sexy…she was everything. We continued to flirt and laugh and she decided to come back to my place with some other people from the party. As we were leaving, she reached for my hand and held it so we wouldn’t get separated in the crowded bar, but once we were outside she didn’t let it go.

Engagement Proposal Ideas in Two proposals: Hawaii (Tantalus Lookout, Oahu + Haleakala, Maui)

The tension between us was pretty insane, and just before I could say anything, she pushed me up against the wall of Porta and kissed me. Fireworks…electricity…chemistry…call it what you will but I could feel a million emotions at once. I felt as if I could feel everything she did and could not help but want more. We spent the night together, talking, flirting, kissing, ect. and it still to this day is a night I will never forget. While laying in bed, Lisa turned to me and asked if I wanted to go somewhere – I remember thinking it’s barely 5 am where could she possibly want to go, but at that moment I would have gone anywhere with her. We got in the car and drove to a spot a non-local person like myself would never know existed. We went behind this building that had lots of graffiti from over the years and lead to a bunch of rocks and broken off cement pieces on the beach. She sat down and signaled for me to come sit next to her and we stared out into the horizon. We watched as the sun rose above the horizon and listened as the waves hit the rocks below us. It was absolutely breathtaking. Was this real life? Was I really watching the sunrise in the arms of this beautiful girl I had met only hours before? How was I already this comfortable with her? I didn’t want any of it to end and little did I know it would be the start of something incredible.

Where to Propose in Two proposals: Hawaii (Tantalus Lookout, Oahu + Haleakala, Maui)

It was that moment, hours after we met, that I knew I loved her and that my life was about to change forever. We got breakfast with the rest of the stragglers nursing their hangovers at my apartment and I invited her to be my date for my elusive roommates’ pool party for her birthday. To my surprise, Lisa jumped at the chance to spend more time together, and we hung out for the rest of the day. There was so much PDA at that party that it makes me laugh a little now to think about how much I didn’t care what people thought. I just wanted to touch her and be with her. People were coming up to us asking how long we’d been together and we would both just laugh and smile. When Lisa finally did have to leave, I was texting her like a high school girl with a crush, smiling from ear to ear. I wanted her around, I missed her. What was supposed to be a “one night stand” was turning into something I could not control. She consumed my thoughts and I needed more of her. Lisa came to my house every day after that. We were inseparable. Even if it was only for 5 minutes, it was worth it.

Jaclyn's Proposal in Two proposals: Hawaii (Tantalus Lookout, Oahu + Haleakala, Maui)

She was working nights at the time, which actually worked with my crazy residency schedule, so I could spend my post call days with her and do basically anything we wanted. The next week I told her I loved her…crazy I know. We were laying in bed looking up at each other and the words escaped my mouth faster than I could stop them. I was so embarrassed, apologizing for saying what I did, knowing it was so soon to feel that way, but Lisa took me in her arms, kissed me, and told me she felt the same way and that she had been dying to tell me how she felt since the sunrise. We were “official” after that and we met each other’s friends, families, went to holidays together, vacations, work events…basically everything. After about 1 year of dating, in true lesbian fashion, Lisa and I “uhauled it” and moved into an apartment together. Life was perfect. A few months after getting the apartment, we decided to get a Portuguese Water dog. We named her “Porta” after the place we met. We’ve been living happily ever after ever since.

How She Asked

Although very rare for a residency class to consist of only women, my residency class was made up of 6 girls. Despite the potential for disaster, my 5 co-residents and I were more like my sisters and we got along better than I could have ever imagined. We spent most of our time together at work, but unfortunately, could never all hang out outside since one of us was always on call. One of my co-residents was from Hawaii and in our first year of residency, we made a promise to each other that once residency was over, we would all go to Hawaii to visit and celebrate our graduation. After Lisa and I started dating, I told her about my promise with my friends to go to Hawaii in July 2017 after graduation. Lisa, having family in Hawaii too as well as a bad case of FOMO, said “you know I’m coming too right?!” Of course, my co-residents obliged, as they loved Lisa too, and the seven of us booked our flights to Honolulu.

Unlike the rest of my classmates, Lisa and I decided to stay an extra week in Hawaii so we could see Oahu as well as Maui. I couldn’t believe it, residency was ending, I had passed my board exam, I was going to have my 30th birthday while in Hawaii, and I had a month off before starting my new job. Things were going so amazing and I was about to go to one of the most beautiful places in the world with my best friends and the girl I loved. Naturally, I thought this would be the perfect place and perfect time to ask Lisa to marry me. We had talked about getting engaged before but Lisa stressed to me that she wanted to be the one to propose when the time came. I wanted to respect her wishes and allow her to be the one to propose, but how could I be in the most beautiful place in the world and not ask the woman I love to be mine forever? I tried to feel Lisa out and see if she also had plans to ask me in Hawaii but she kept talking about money being so tight so I was convinced that now wasn’t the right time for her.

I didn’t know what to do…one part of me wanted to respect her desire to be the one to propose, but the other part was like “you love her and you’re going to Hawaii, so just do it!” So I bought a ring that was perfect for her and had the idea of keeping it with me at all times, so in case she did propose, I would have something to give back to her and let her know how much I love her…if she didn’t propose, it would be a game time decision whether or not I was going to. On 7/7/17, the seven of us woke up to go to brunch for one of my co-resident’s last day in Hawaii. Lisa’s work phone was going off like crazy and she said she had to stay behind and get some work done. Of course, I was pissed, especially being the last day we could all be together, but after some arguing and pouting, we left Lisa behind and proceeded on with our day.

After brunch, my friend asked if we wanted to see a cool lookout point that she used to go to with her friends in high school. Loving any excuse for pictures, we drove up to the top of Tantalus lookout, where you can see mountains, Diamond-head crater, the city of Honolulu, the coastline and the beautiful blue water. I was so into taking pictures of the landscape on my phone, that I nearly missed Lisa, wearing all white, walking toward me from a bed of white flowers. I put my hands to my mouth, in total shock, when she bent down on one knee and asked to marry me. Her eyes with the sun hitting them just right, I swear you could see forever. I couldn’t believe it. I looked around and my friends all had their phones taking pictures – they had been in on the plan all along. I was so happy, but at the same time, a little bummed since I did not bring her ring with me that day since she was at home.

My immediate family, Lisa’s family, and my 5 co-residents had known all along Lisa was planning to propose, but they also knew this was my plan too! So many people keeping two different secrets! I decided it would be best to wait for my proposal until we got to Maui. We left our friends and head off to Maui to spend the last week of our trip alone together, newly engaged. We had planned to do a sunrise tour up on top of Haleakala, the highest point on Maui. I thought it would be full circle, watching a sunrise the day we met and then watching a sunrise together nearly two years later and newly engaged.

When we got to our tour bus, they started handing out gloves, windbreakers, and pants…a little strange for people who were just in shorts and tank tops. Apparently, since Haleakala is 10,000 feet above sea level and its 4 am, it is FREEZING up there. We got there and people are huddled up in blankets, some not even getting off the bus since it was particularly windy that day. My plan of proposing at sunrise looked like it wasn’t going to happen since I could barely take my fingers out of my gloves and the wind nearly blowing us away.

Despite the weather, the sunrise was just as beautiful as the day we met. Lisa took me in her arms and said “Do you remember when we watched the sunrise together the day we met? And now were watching another sunrise engaged…” At that moment, I knew I had to do it. I said to her “well, were only half engaged…” I asked the couple behind us to hold my phone (recording of course) and I bent down on one knee and asked Lisa if she would marry me. She was so shocked! She didn’t realize I had a ring this whole trip too! My trip to Hawaii was one of the most incredible trips I’ve ever taken.

Watching someone make such a declaration of love to another person in a place as beautiful as Hawaii…it was an absolutely amazing feeling and truthfully an out of body experience. I’m happy Lisa was able to have that too. It is truly a feeling you cannot put into words. In retrospect, I am happy it happened the way it did and that I did not have Lisa’s ring the day she proposed to me. It gave us both an opportunity to feel special and feel loved.

Our two proposals were so different and at the same time, so perfect. All I know now is that I cannot wait to spend the rest of my life with her and make her my wife.

Special Thanks

Krishanna, Gopi, Shonte, Priya, Maria |
Photos, Videos, Secret keepers!