How I Got Engaged to a Girl from Craigslist and Then Ruined It
I lost my job, broke off my engagement, she kept the dog, and I went damn near broke
“Are you happy?” my therapist asked. I never once questioned my happiness in the three years my ex-fiancée and I were together. “I thought I was, but now that you ask, I’m not sure.”
Social media as a spectator sport. Onlookers were baffled by what transpired in my life this year. Peer into my life through the framed displays and you’d have found an Instagram-perfect couple that lived a life to be envied, yet relatable enough to any young NYC couple. A small town girl, she was as pure as the heavens and as sweet as a candied rose with a classic sense of creativity that was most fitting for her fashion design career. A city boy, I was an investment banker who believed in the notion of grit, passion, and perseverance and had worked my way up to the crème de la crème of banks, emitting an intense but friendly sense of social energy along the way.
And yet, there I sat face-to-face with a stranger discovering how blind I was to my narcissism, character flaws, insecurities, and win-at-all-costs attitude. Sophocles would’ve been proud, and Nietzsche would’ve said, “I told you so.”
This is my story for those who can relate and the lessons I still have to learn.
August 15, 2013 — Roommate Wanted
I had just ended a previous relationship and was saddled with the financial burden of a NY studio lease. Like any New Yorker, I turned to Craigslist for a creative solution.
$1000 SharedStudio/drman/elev/laundry Immed (Midtown)
My friends thought I was crazy, probably rightfully so, but my phone buzzed with interest anyway.
There she stood at my doorstep as radiant as the sun with a smile that melted butterflies. Our eyes met briefly, both bashful from the mutual attraction and gleefully surprised that we both dodged the minefield that is Craigslist…or so she thought. I knew from that moment that I’d marry this girl.
Unbeknownst to us both at the time, my narcissism was like a slow toxin masked by the false pretense that everything I did was for the benefit of our life together. It took nearly 3 years to rear its ugly head all the while sapping the heavenly joy from this gift from the heavens.
October 8, 2013 — Her Surprise Birthday
The big city is a lonely place. Coming from a small, Canadian farm town, she was not one for extravagance, but was the type who found meaning in everything. Her gentle, untainted soul drew out your natural instinct to want to protect such rare purity from the harshness of the world, and at the same time making you want to show the world that such beauty can exist. This is my roommate, and she deserves a proper birthday.
I implored two of her dearest friends to invite more of her friends. The guest list increased by 1. My heart sank. Nevertheless, I was determined. I put the call out, and my friends gathered in support.
We hid in the dark as she innocently entered with curiosity. “Hello? Why are there so many shoes here, and why’s it so dark in here?”
“SURPRISE! Happy Birthday!” Her eyes glistened with watery, heartfelt joy. The kind of joy that is only evidenced in the eyes of one who’s been through a real tragedy in the past.
October 12, 2013, 3:50 A.M. — Lust
It’s been 2 months of living together in the confined spaces of our NY studio. Either Stockholm Syndrome was taking hold or this chemistry that’s been building between us is becoming more and more real. Day in and day out, I try not to be that creepy roommate. I try to avoid noticing her ravishing silhouette or the way her dress gracefully flows with her kitten-like steps or how her natural beauty is indistinguishable from her made-up face. We hang out together, and I get excited introducing my wonderful roommate to my world. My friends all thought with the way I talked about her, it was only a matter of time.
One night, our gaze locked. I held her close. Her lace slip teasing the curves of her elegant form, her lips soft as a cloud. I pulled her closer, her nails dug deeper, and our hearts raced playfully together. This is us.
December 25, 2013 — No Such Thing as a Vacation in Banking
I sat at the kitchen counter and worked through Christmas dinner while the rest of her family ate and looked on with disappointment and pity. While completely oblivious to the rudeness of my presence, I had also not recognized the anger and shame that was brooding inside her…until later that evening.
The idea of sleeping in the same bed before marriage is still seen as inappropriate in the eyes of her mother, even though we share the same studio. Her mom’s under the belief that we still slept in separate beds. So I went back to her family-owned motel with her older brother, and they went home just a few minutes away. We talked on the phone; reminiscent of high school dating.
“I can’t believe you tonight. That was so embarrassing!” My eyes opened wide, confused by the impending shit storm that was about to unfold.
“Work is work,” I said. “I had no choice! We had a deadline that evening, and yes it sucks that it was during our Christmas dinner, but in NY it was already getting late because of the time difference.” Talk about two people being on completely different pages, we weren’t even in the same book.
“I thought you had this week off to spend with the family.”
“We never truly get days off. We are just on-call, but we can work remotely. What else was I supposed to do?”
“If I had known that then I wouldn’t have asked you to come to Canada at all!”
“I wanted to at least be able to meet your family and spend some time with them. But work takes priority! How do you think I’d be able to afford these trips, our lifestyle, and everything else! If I don’t do the work when needed, then the next guy will, and I’m out of a job! I worked my ass off to get here. This is what I fucking do, and why they’ve kept me on versus anyone else. My associate with an MBA is useless and can’t do shit, so I have to do everything for him!”
I became infuriated because my fulfillment of responsibilities was being challenged. Angry shouting ensues. I forgot how thin these walls were. It was embarrassingly awkward in the car with her brother the next morning. I felt so ashamed. How could I talk to someone I love the way I did that night? It’s inexcusable. I never would’ve thought I’d be the type of person who could ruin a Christmas dinner, but that’s exactly what happened.
Reflecting back, I now realize this is where I’m psychologically messed up. I’m insecure about my value to my employer because I came from an empty background, so I overcompensate and never developed a backbone to stand my ground when it came to priorities. I unnecessarily twisted the issue at hand into something even grander than what we were actually arguing about. I rationalized my priorities, not realizing how rude it actually was to small-town folk and perpetuating the douche bag imagery of New Yorkers, by turning it into a challenge of my role of putting food on the table for us and working for the sake of our entire future together. What she’s told me several times was that I’m never living in the present. Like I’m there but not really. I never understood that until now.
May 24, 2015 — Marshmallow
Girls are pretty sneaky in getting what they want. We stopped by a local pet store because she wanted to play with some puppies. Sure, why not? The dogs were all cute and stuff; whatever. Then she sat me in a chair. The clerk brought over this little ball of fluff and placed him in my arms. I turned to putty. And then we saw the price tag. “wtf.” A bit heartbroken, but determined, we visited several more pet stores looking for the same white Pomeranian for a cheaper price. Yeah, we found white poms, they were cute and cheaper, but just not the same affection. I insisted we go back to him. I wanted him. We named him Marshmallow.
Never before in my life had I been filled with so much love and adoration with my beautiful, adoring girlfriend and the most lovable puppy in the world. My life was complete.
May 5, 2016 — The Ring
For men like you and me, here’s a big secret. The engagement ring is never a secret; only the timing is.
Marriage talks have been on the table for quite some time. We both agreed it would be a terrible idea to entrust me with picking one out, so she picked it out herself. We visited the store, she tried it on, it was all a very exciting experience for her. As a possible sociopath, I’ve been told I lack empathy. I’m excited for her, but to me, it’s just another step in the process of life. All I had to do was decide how much to spend on the diamond.
Funny thing about budgets. They’re a lot like New Year’s resolutions. She picked out the Hazeline Three Stone Ring from Anna Sheffield. It was perfect. It embodied everything about her from the balance of the yellow gold that seamlessly blended with her skin tone and the clarity of a white diamond center. It had a tasteful royal crown aesthetic that invoked a sense of je ne sais quoi. But there was one element that felt off.
I arranged to go see their G, F, and E color diamonds just to see what the difference was all about. The base model on display had the G diamond. It was dull and lifeless. The F looked fine, but the E…the E sparkled with such natural brilliance that would come to represent her eternal beauty that I get to witness every day. It made the ring complete.
June 8, 2016 — Towels
We fought about towels to the brink of tears. I said really hurtful things that I didn’t mean because I’m an asshole who lacks restraint.
“I think it’s sweet that Jason gave Sarah his credit card to use. Of course she uses it sparingly but it’s a nice gesture on his part. Would you give me one if I asked?” Little did I realize, she was testing me.
Any guy with any sensibility would’ve planned his next words very carefully. Not me, of course. “Why do you need it? You’re working too.”
“To buy the more costly stuff we need like towels.”
“You’re telling me you can’t afford towels?”
“I’m not able to save much at all especially because of the rent we pay.”
“If you’re spending beyond your means then we should figure out what expenses you can cut back on. How much do you even make?”
“What does that have to do with anything? I knew I couldn’t ask you for something like this.”
“But I already pay for almost everything. Dinners, bulk of the rent, utilities, all activities we do together, vacations, weekend trips, vet expenses. How can you not have any savings? I don’t want to make this into a gold digger relationship.”
If there was ever a time for me to shut up, this would’ve been it, but I didn’t. She told me to shut up. I didn’t. She screamed at me to shut up. I didn’t. I kept making up all the rationalizations in the world for my twisted logic ever escalating the issue to the point about our entire lives together into the future. It got to the point where I asked her, “So you’re telling me if I proposed to you, you wouldn’t say yes?” (I had bought the ring at this point).
“I would say no.”
And this all started with towels?
Well, for what it’s worth, my logic was that I wanted to make sure she could independently support herself in case anything ever happens to me in the future and not be too overly reliant on me. She, on the other hand, just wanted to feel like I would take care of her when she needs me the most and not have to pull teeth for every single thing. I always thought that I was being clever in looking at the bigger picture. But now I realize, I’ve been looking at the wrong picture the entire time. Just like the book, I really am from Mars.
July 2, 2016 — The Proposal
She went to play in the ocean while I sat on the Mexican beach plotting with her best friend the events that were about to unfold that evening. “Are you sure you want to do this? What if she says ‘no’?” her friend asked. I went on the defensive thinking she was challenging my commitment to her or the state of our relationship and failed to read between the lines. The fact is, I had forgotten all about our last fight, or any of the fights for that matter.
Her friend pressed further, and I previewed my twisted mentality with her. I explained to her why this was going to be successful, “Because I’m doing this in front of her closest friends in the most romantic setting with a proposal straight from the heart. She will have no choice but to say ‘yes’.”
The day you showed up at my doorstep was the day I knew I found the one
At first, I was afraid you were too good for me
You were and still are as pretty as the eye can see
Then I learned that I can make you smile
That made every effort worthwhile
Whenever I made you frown, I got scared that what we had would drown
I would tell myself that you deserve better, so better is what I’ll strive for together
Being with you makes me happy
Just like our dog with my sock, I hope what makes me happy will make you happy too
What I’m really trying to say is, will you marry me?
June 3, 2017 —The Breakup
What started out as routine wedding planning frustrations quickly escalated into the biggest mistake of my life. Seemingly out of nowhere, she drops this saddened remark.
“I’m not happy”
“What do you mean you’re not happy?”
“I don’t know if we’re good together. What if I don’t want kids?”
Ignorant of what she’s really trying to tell me, my heartbeat flared, and I went on the defensive. “I think we’re perfect for each other. Why wouldn’t you want kids? Our children would be so beautiful.”
“I did before, but I don’t think I can see myself having kids with you because of the way you’ve been treating me.”
“What are you talking about? I’m sorry about our last fight. I just got frustrated because you couldn’t see my perspective.”
“This is something that’s been hurting me inside for a while. I think I need to move out and have my own space.”
“It doesn’t make sense for us to live separately while we’re in the same zip code. It felt like you always had one foot out the door. We just put down a $10,000 non-refundable deposit and you bring this shit up now?!”
“We can get it back can’t we? We only put the deposit down a month ago.”
“It’s NON-REFUNDABLE, that’s the point of a deposit!”
“Well, I didn’t know that! Let’s try to ask for it back.” Her voice quivers. Her hands unsteady. “I’m not happy. I’m really, really sad. I can’t live here anymore.”
“What about the whole wedding then? I’ve already told my whole family, and they’re making plans to fly out for this.”
“I can’t. I don’t want the wedding or the engagement on the table anymore. None of it. I just need my own space. I need time to myself.”
“I don’t want you to leave. I can change, I promise. It just takes me some time. I know I can be an asshole, but I’m working on being better.”
“You haven’t done anything! You keep saying you’ll change but you never do. You haven’t even made any effort. I’ve made all the effort.” She was right.
“What are you talking about?! It’s not easy to just change overnight. I just need more time to practice and work on myself.”
“You need to see a therapist. My friends said so too”
“Fuck them. I’m not seeing a therapist. I know I can change on my own. Therapists are a fucking ripoff. They don’t do shit for me.”
“I’ve gone to therapy, I’ve talked to people, I’ve tried everything and put in all this effort, but you haven’t done anything at all! I’ve been so, so depressed. I just need to move out and start fresh. I can’t do this anymore.”
I exclaimed, “I just took this fucking boring ass corporate job so that I could spend more time with you and our future family instead of going back to banking! Isn’t that what you wanted?”
“No! Don’t put that on me!”
“What’s the fucking point in dating if we’re going to live separately? Then let’s just break up. That’s what you want isn’t it?”
“No! That’s not what I’m saying!”
“What’s the fucking point then? Sounds like a break, I don’t believe in breaks.”
“I know you don’t…Then maybe you’re right, maybe we should break up.”
“Let’s just fucking end it here then,” I concluded.
…
“Aren’t you sad at all?” she asked with fragments of her torn heart streaming down from her flushed cheeks.
“Of course I’m sad…but at the same time doesn’t it kind of feel like a weight’s been lifted off our shoulders?” I could feel the darkness inside her dissipating and leaving behind an empty sadness.
Strangers Again
I thought that if I had to see a therapist, then that must mean that I’m crazy and would have no control over my own behavior. That was so far from the truth. I conceded and went to see a therapist because I wondered to myself, if her friends were also saying I should go, then either I really am crazy and couldn’t see it or they were wrong about me. I had to find out for myself.
Through conversations with my therapist, I discovered how blind I was to all the deeply rooted insecurities and poor behaviors that I’ve developed over my lifetime. Some of it is from my upbringing as a first-born child of immigrant parents where I had to pioneer my own path forward or reinforced by many years as a banker working in a high pressure, no-tolerance-for-error environment. Is recognizing these issues enough to invoke change? I don’t know. I just know that this was all too little, too late. As cliché as it might be, I really should’ve learned to just listen for once in my life. I don’t have an ending here because I remain hopeful that us separating is the first step in our journey back together.
Not to make any excuses, but there is one thing that I wish had happened. I wish someone had held a mirror up to me sooner.
What I’m left with, however, is an existential question on whether or not I should let go. My friends tell me that I need to move on. But then I ask them, in the name of love, if you knew with absolute certainty that you were meant to be with someone, wouldn’t you do everything you can to make that dream a reality? Would entrepreneurs be as successful if they gave up at the first sign of failure? So far, I’ve failed at every personal goal in my life the first time around, but I worked hard and eventually achieved them (and then ruined them). Knowing that there’s a strong possibility that I could be dead wrong about all this, I’ll still subscribe to that moon shot chance of being together as long as I have hope. Even if that hope is just a fantasy.
My biggest fear is that the next time I talk to her, I’ll realize for sure that there’s nothing left in her heart for me. So I stopped asking to see our dog, and I continue to dangle this carrot of hope in front of me as a constant reminder to be better than I was the day before, just in case.
If you know someone who could learn from this story then do them a favor and share this with them. I appreciate the claps below. You can read my follow-up post here “What She Did For Love”
