I’m terrible at keeping surprises. My girlfriend knew I was proposing weeks before I actually did. As you can tell from the headline, I proposed to my girlfriend recently, and thank Jesus she said yes.
And I also hate to ruin this surprise too: my life didn’t change at all after getting engaged. Sure, I call my girlfriend my fiancee now. Friends who haven’t spoken to me in years reached out to call and FaceTime me to congratulate me on the engagement and proposal. Suddenly, I became the most popular person in my social circles as my phone got bombarded by hundreds of notifications.
Otherwise, my wallet is significantly lighter. There’s a lot less money in my bank account than there was before. My parents expressed some trepidation, anxiety, and excitement that their baby was getting engaged.
But otherwise, my life is 99% the same. I still have to go to work in the morning. I still have to worry about how I’m going to pay rent and how I’m going to stay on a budget for the next couple of months after all the money I spent on the engagement ring and the trip to Key West for the engagement. My girlfriend and I are still doing relationship counseling to work on conflicts in our relationship.
Immediately after getting engaged, my girlfriend (now fiancee, and it’s going to take me some time to get used to that term) started looking at wedding venues and asking for opinions on them. I had no idea we would start planning our wedding immediately, but I’m all for it and figured it’s better to get as much planning done as possible immediately. I am certainly stressing out about my friends and family — who is invited and who isn’t. But that’s a problem for another time and likely a universal concern for anyone who has ever gotten married.
I’m also very nervous for how much this wedding is going to cost. If the proposal broke the bank, then I don’t even want to think about how much the marketing scheme of the wedding industry is going to charge me to meet our expectations.
The expenses to propose to my girlfriend were not cheap in the slightest. General convention says you have to spend three months salary on your engagement. I have no idea who came up with that rule, but I felt myself cringe when I had to call the bank and explain why this transaction in the mid-thousand dollar range, exponentially more expensive than any other transaction I’ve ever made, was not a fraudulent transaction.
Despite my life not changing much, the proposal and our vacation for the proposal was the experience of a lifetime. I also paid $750 for a photographer to hide out in the trees and take pictures.
This is the story of my proposal and engagement.
My proposal looked absolutely nothing like a Hollywood movie. It wasn’t a surprise largely because my girlfriend and I have been talking about getting engaged for a long time. Our relationship was still in its early stages six months after we dated, and then it accelerated drastically.
COVID-19 forced us to quarantine together and spend a significant amount of time together. Our relationship was 100% in the honeymoon phase before then. We never fought. We never really argued. Every moment we spent together was time we had a blast and spent romantic time like a Hollywood movie. We would see each other a couple of times a week as we had incredibly busy work schedules.
And then we spent so much time together that the honeymoon phase wore off. We started fighting and bickering over small things. My girlfriend is significantly more clean than me and has much higher standards. While she tolerated my messiness in the early stages of our relationship, I had to grow up and mature and become cleaner as the relationship wore on.
Another point of contention in our relationship is the quality time we spend together. I spend a lot of time on my phone. I spend a lot of time working after business hours, whether that’s on my numerous side hustles or my job. Again, this was okay for the early stages of our relationship as my girlfriend and I were just getting to know each other. But as the relationship wore on, she expected more from the time we spent with each other, for our dates to be interrupted and for me to finally turn the damn phone off.
Suddenly, we were arguing more often than before. And we had drastically different styles of approaching conflict. I am an incredibly non-confrontational person. I saw my parents fight all the time when I grew up. I heard my father scream and yell at my mom for what seemed like whole days on end, while my brother and I tried to distract ourselves from the fighting. I resolved I wouldn’t fight with whoever I was with later on in my life. It wasn’t a very realistic resolution, but I wanted any relationship to not be like the failing and terrible marriage of my parents.
My fiancee, by contrast, says she inherited her father’s hot-headed nature. Her first instinct when she is unhappy is to react with anger. In particular, she gets very upset with me when I leave the bathroom a mess. I don’t respond very well to anger and tend to just shut down, like I did when I was a kid. But as the relationship has progressed, we’ve come to more middle grounds and worked on our relationship. It’s not perfect, as no relationship is. But we have grown a lot together and truly love each other.
We went ring shopping a couple months ago. I didn’t know the procedure to ring shopping at first, and from the societal narrative and Hollywood movies I watched, I thought I was supposed to buy the ring as a surprise and completely blindside my girlfriend by asking “will you marry me?”
It turns out this is not how most proposals go, at least in my anecdotal conversations and observations. I had one friend buy a ring and surprise his girlfriend with the proposal. She would tell me several years later how upset and unhappy she was that she didn’t get a say in the kind of ring she would wear the rest of her life.
Regardless, I put no budget on how much I would spend on the ring. I merely wanted my girlfriend to be happy to have a once-in-a-lifetime experience. We went to a jeweler, where she and someone at the desk talked and tried on rings for hours. I listened, but I just sat there as the logistics and nuances of diamonds went completely over my head.
We were between a couple of rings, but the jewelry store would take a week before the ring was actually delivered. We went to the store again to actually buy the ring. My girlfriend was there while I bought it, which further limited the element of surprise. While she was far away enough not to hear the price or my plans for engagement, it was pretty clear our engagement was happening soon.
While I wasn’t going to ask my girlfriend directly what she wanted to do, she dropped me a ton of hints, most of which I was completely oblivious to. She talked at length about how she wanted to go to the Caribbean and spend the summer vacationing in the tropics. She sent me Instagram messages and Tik Tok videos of vacationing in the Caribbean of which I only really looked at half of them.
To get the proposal right, she requested I talk to some of her closest friends. And so I did. For weeks, I checked in back and forth with her friends to get an idea of her ideal proposal was, since I was bad al listening for hints and paying attention. They said she wanted to have her proposal in the tropics as well, and she wanted to be well dressed.
We floated around various ideas. First, we thought about Hawaii. But I Googled “flights from Baltimore to Hawaii” and instantly found the cheapest possible flights in the thousands. Also, I am working a full time job over the summer where I can’t take many days off. A single flight to Hawaii would have taken a whole day to get there and come back, making it a complete non-option from a time and budgetary perspective.
Then we floated around ideas all over Florida. I thought about St. Augustine and Naples, but her friends thought there would be better options, particularly in the Keys or Puerto Rico. I obliged and decided on Key West, and then we thought about the timing. My girlfriend and I started dating on July 26, 2019. I wanted to plan closely in line with our two year anniversary.
A couple of weeks before, I visited her parents’ home in Huntsville, Alabama. There, I was trying to find an occasion to be alone with her parents and ask for their blessing and permission in marriage. However, we never had a time we were completely alone or a good excuse for me to take them to dinner. And my time there was running out without me coming to do what I came there to do.
I asked formally if I could talk to both of them privately, and asked for permission and blessings in a long conversation where they made sure I would put their daughter first. Finally, after about 30 minutes where we had serious conversations about their marriage, their obstacles, and what they expected from me as their future son-in-law, they gave their permission and informally welcomed me to the family.
Over the course of the next couple months, I booked our flights. I booked the hotel. I planned how we would actually get to Key West, and decided to fly to Fort Myers and take the ferry.
I thought I had it planned perfectly, but I was actually very wrong. The ferry only ran once a day, and we were on a tight schedule due to my work schedule. This made the ferry a non-option given the amount of time we wanted to spend in Key West. Since the flights to Fort Myers were already booked, I looked up how long it would take to drive from Fort Myers to Key West. Google Maps told me three hours, which wasn’t bad. I promptly booked a rental car and thought I did a great job.
If you live in South Florida, you will know the drive from Fort Myers to Key West is, by no means, three hours. Once I arrived, I put the trip in again to Google Maps. This time, it showed me we had to take six hours at the minimum, taking toll roads and not factoring in stops. This drive would be absolutely miserable. The scenery was beautiful, don’t get me wrong. But the traffic would be terrible on a Saturday when it seemed like the whole world was going to Key West. Also, once we got into the Keys, we would regularly encounter speed limits of 35 or 45 miles per hour and police officers seemingly everywhere. For a 300 mile drive, this made it take much longer than intended.
My girlfriend banned me from planning any more vacations. That’s probably a good idea.
The week prior, she actually asked me if I was proposing and asked if I could hold it off. As a stingy person, she knew it was a special occasion if I was willing to fly her out, book a nice hotel without reservation, and spend thousands of dollars on a vacation without complaining. I guess I was bad at keeping a secret in that regard.
Due to scheduling conflicts and bureaucratic glitches, we have not done as much relationship counseling as neither of us would have liked. We discussed the future and our plans for our careers, kids, and where we want to live. She didn’t feel like we were ready, and this felt like a devastating gut punch because I had already invested so much emotionally and financially into the proposal. Despite not having as much counseling as we would have liked, I already bought and insured the ring. I already put in thousands of dollars to pay the photographer, book the hotel, book the flights, the rental, and make plans.
I probably did make the proposal obvious. And I said I wouldn’t propose at first as my girlfriend and I talked about where we wanted to live in the future, and the compromises we had to make. It was the first time we were having these conversations over life-altering decisions, ensuring our communication was a lot better. The week before we went to Key West, we talked every single night about what we wanted and how we could come to a middle ground.
And I felt the same devastation I felt when she said she wanted me to wait to propose. I wanted to respect her wishes, but I also felt like all my plans and all my hopes were wasted. It stressed me out all week more than it should have, and I realized I wasn’t comfortable making the sacrifice. I asked her if she would be okay with me proposing while we continued counseling and continued talking about our future plans. She said yes, and the plans were back on.
Once we actually got to Key West, we checked into our hotel and breathed a sigh of relief. We went to one of the most popular and well-reviewed restaurants on the island, Blue Heaven, and had a nice dinner. My girlfriend was scared I was going to propose then and there, and fortunately, I did not.
The next day was a very packed schedule. At the hotel, I got a romance package for myself and my girlfriend from the hotel we were staying at. But I did not plan ahead well. The housekeeping staff would leave in the afternoon, and the hotel staff would leave at 7 p.m. The proposal was planned for 8 p.m., but we had to come back to the hotel numerous times to get changed, shower, and engage in various Key West activities.
In the mid-afternoon, we went parasailing and had to come back to the hotel numerous times. The housekeeping staff put out pedals of roses all over the bed and folded two towels into swans. The hotel staff told me they could wait to give the wine for when we returned later in the night, just before we got back. I forgot or just neglected to inform them we would be back numerous times.
And so when we returned to the hotel at around 4 p.m., the two staff members at the front desk were looked absolutely shocked and floored to see me. I tried to give a coded message in “we’ll be back later,” but they stared bewilderedly at us while we walked to our room. While we got changed and got ready for parasailing, they knocked on the door with two glasses of wine and a bottle of Prosecco. I had to wave them off and tell them we weren’t ready yet, and they understood.
Fiascos like this would happen the whole rest of the day. I answered a call from the rental car’s sound system from a random Key West number. It was a voicemail — from the photographer, blasting through the whole car with myself and my girlfriend in it. As soon as I realized, I cut off the voicemail as my girlfriend chuckled and shook her head.
Once it got closer to 8 p.m., I was getting nervous. I planned the photographer on such late notice there wouldn’t be flowers at the beach we were getting on. Not only that, but my girlfriend got the hint I would be proposing when I dressed as nicely as I did all trip and said she should do the same for a fancy dinner. She took a while to get ready and look as nice as possible, but it was almost 7 p.m. and we still had not left for dinner yet, and I had to get us to the beach by 8 p.m. on a very tight schedule.
We got to the restaurant around 7 p.m., and I had to calmly tell the waiter to please skip appetizers and have us just order entrees and drinks. I frantically ate as fast as I could while motioning for my girlfriend to do the same, religiously checking my watch to make sure we could leave and get to the beach on time. The ring was also bulging very explicitly in my pocket as a big box, and I kept trying to keep my hand over it and hide it under my shirt so she wouldn’t notice. It was obviously not my wallet, so there could be no good explanation for why there was a huge square on the left side of my pants.
We did make it on time after much rushing, but as I checked my phone walking to the car, I got a string of consecutive texts from the photographer. She requested we change our location on the beach. Apparently, despite the beach usually being not crowded and relatively remote, there was a man screaming and yelling at everyone who passed by, belligerently drunk after having one too many. She gave directions so the man would not be in our shot.
I didn’t think it would be that much of an issue, but as we arrived at the beach, I saw what she was talking about. I didn’t pay the man much attention, but he yelled at us and his behavior was scaring my girlfriend. At that point, I was way too committed to stop. I made sure she was facing the sun and I wasn’t and gave my speech.
In retrospect, I should have written it down. It was incredibly awkward because I forgot half of what I wanted to say. She said it was a good speech that told how much I valued our relationship, but it was also long, and people were staring at us. To his credit, the belligerently drunk man on the beach stopped yelling and screaming for the duration of the proposal and the photos, allowing us to have our moment.
I got on my knee and asked her if she would marry me. She started crying and said yes. The photographer said to stay on my knee longer than I thought I needed to, she even though she said yes, I stayed on my knee. My girlfriend kept asking me why I was still on my knee in an awkward 20-second span, but finally, we heard a bunch of snapping and flashing lights as the photographer kept taking pictures of us. I finally got up, and we kissed as a newly engaged couple.
I thank God the proposal went well and I have the best fiancee in the world. It’s through the grace of Christ we met each other and are able to be with each other for the rest of our lives. I thank God the proposal went smoothly and as well as it possibly could have, and I thank God my fiancee and I will be married soon and bound by a covenant to serve Him. I prayed for a long time and will continue to pray for clarity and guidance on our relationship, and I hope we can keep putting our faith in God first to guide us through the dark and rocky periods of our engagement and subsequent marriage.
We don’t have the photos yet, but from what I can tell the photoshoot went incredibly well. The proposal, engagement, and everything that went into it was the experience of a life time. It was life changing in that we’re both moving onto a significant portion of our lives and moving forward in taking the next big step in our relationship.
However, our daily lives haven’t necessarily changed at all. We’ll probably have to start filing taxes together soon and we can check off “Married” under a lot of boxes. We will also have much less money at our disposal after the wedding. But we still have to worry about the same things as life goes on. We still have the same friends. We still have to go to work and work the same jobs. We still have to attend to housework and logistics. And we still have the same problems we always had in our relationship and in normal life.
So in totality, I would argue our lives haven’t changed that much. But as slight as the 1% change in our lives really is, it is symbolic and significant in its own right. And I am incredibly grateful she said yes.
Originally published on July 27, 2021 on Medium
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