Losing the most incredible person you’ve ever met

I’ve been seriously down in the dumps after breaking up with my ex, and wanna hear similar stories from you guys and the WSO community. I’m 21 fyi so I know I have a lot of people left to meet in my life, but she genuinely changed the game for me. She was by far the most intelligent and beautiful woman I’ve ever met. Absolute 10/10 with the most intricate, unique personality I’ve ever encountered. She left me with a vague explanation as to why, but given geographical circumstances it was pretty much impossible that the relationship would survive post college (US whereas she probably will head back to europe). A natural leader, incredibly mature, selfless in everything she did, and kind to everyone she met, truly one of a kind. She also helped me through a serious crisis period as well which I don’t know how I would’ve gotten through without her. The only person I’ve ever met who I felt truly understood me. Let’s gather round this table boys. What’s the worst heartbreak you’ve ever been through, what was she like, and how did you eventually move past it?

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*and quit simping over how amazing someone is when you're 21 you goon

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I wouldn't say she was the most incredible person I've ever met, but we were deeply in love. It started at 6th and B in the East Village NYC. I was living in a true 4BR with my bros. Two moved out and my roommate and I decided to interview two girls to move in - in their place. I posted an ad in Craigslist and said lots of details about us and the place and that only girls need respond. I requested they email back with social media links so we could see if they were hot/cool or not. 

I received about 50 responses as this place was really cool. My roommate and I interviewed about 10 people and picked two. A blonde British chick who was about 25 and a 20 year old FIT (Fashion Institiute) student. All 4 of us set the ground rules that we couldn't hook up with each other as we were roommates. Well, that didn't happen. I fell for the fashion student and she fell for me hard. I was 26 at the time.

Let's just call the FIT student "Jane." At first we kept our relationship a secret, but it was no secret in the house that we were really vibing with each other and on the same level. We were super stoners and made each other laugh and went through endless adventures around NYC, taking lots of photos along the way. I never cared for someone as much as her. The roommates and our friend groups finally found out we were dating, and we made it official on Facebook.

Every day was a great day with Jane. I was WFH and when I would finish with work, we would smoke a fat blunt and hit up the city. She turned 21 finally and we could go to bars in NYC. We went to Mexico together to a little surf village called Sayulita and visited her family in Florida. Nothing could stop us. It was us versus the world, and we were winning. She picked out a whole new wardrobe for me at Urban Outfitters and we were super stoner super hipsters. 

She was the first person I said I love you to and she said it back. The first person who ever said I love you to me was this UVA chick I met in Spain, and I didn't say I love you back to her. Jane seemed like she was the one. But, she had more time on her hands than I did and even though I was WFH, I started going into the office to get work done because Jane was a distraction at times. We began to fight about how much time I was spending with her and I became frustrated at one point and said we were done. 

Jane called her Mom that night in tears and her Mom took a red eye flight to NYC and was at our apartment at 6:30am the following morning. Jane said she would do anything to get back together with me and her Mom took over the conversation and argued every complaint I had with the relationship and successfully negotiated on Jane's behalf for us to get back together. I agreed to give it another shot. 

Things seemed to be back to normal. Jane backed off a bit from bugging me about time with her versus time working. I decided to resign my corporate finance / management consulting job to go out on my own. Jane's Mom was a PE recruiter and told me if I didn't make it on my own, she could hook me up with a PE job in NYC. So I started a financial design / art design company and consulted a client on a small M&A deal and sold some abstract art paintings to friends in NYC.

The sales in my new company were lackluster and I found it was difficult to wear all the hats in a company. Sales/revenue generation proved to be my weakest point and I underestimated how hard it was to find and take on new clients. I started to stay up all night, lost my circadian rhythm, and was so stressed about my company making it that I went hypomanic and eventually manic. Jane said she would be with me no matter what. 

Jane lied. I was institutionalized for mania in NYC and it was too hard for her to bear. She wrote me a dear John letter while I was locked up and it was the absolute saddest day of my life. She wrote how much I meant to her, how much she cared about me, but that she had to let me go. I got out of inpatient care and came back to an empty apartment. She couldn't bear to face me and her Dad flew up from Florida to get all her stuff. Her Dad was harsh to me and I remember him saying "I will never let my daughter date or marry a bipolar person." Great, that made me feel absolutely terrific. I was dealing with this new diagnosis and had to live with the stigma of others as well and my girlfriend was gone. 

So, I decided to take up Jane's Mom employment offer in PE, but when I contacted her, she said she wouldn't help me anymore, so I was all alone and underemployed with her empty room just tugging at my heart. I made her a Valentine's day painting that her Dad hadn't packed up yet and told him I was taking back the painting. She didn't deserve it. I started crying, he started crying. It was a real mess. 

I began to question my existence and purpose in life. I didn't have a manager to tell me what to do, so I sought a higher power to tell me what to do. I would serve God in my LLC and devote my life to helping others. Each day I began to question my purpose more and more. I kept asking myself and asking God what I could do on this earth to make Him the happiest?

I got fresh Ink at East Side Ink tattoo of Isaiah 53 5 in Hebrew on my shoulder and started going to my local Catholic church (St. Stanislaus) on 7th Street in the East Village. I began to learn Polish and was taking notes in Polish and eventually got to the point where I felt the calling to serve God as a Catholic priest. The Pauline Fathers were in charge of this church and I talked to the Pastor about jointing the brothers.

Jane and I started talking on the phone again and I told her that if we weren't going to be together, I was going to join the Pauline Fathers and go to seminary in Poland. She said she didn't want to get back together. The Pastor of the church said if I was interested in next steps, I had to have an interview with the Vocation Director at the American Shrine of Our Lady of Czestochowa in Doylestown, PA, so  I rented a car in NYC and drove to PA to talk to him. 

Well, he was in NJ that day when I drove down. I didn't have an appointment and had left messages on his VM before driving down, but couldn't connect with him. His secretary said he would be back in a few days and I was a bit disappointed and had nowhere to go. I thought about getting a hotel in PA, but met with a very nice lady at the Shrine and she invited me to a BBQ at her house and I met her family and friends and they took me in for a few days at a very nice house in Doylestown - complete with a hot tub, pool, and gym. Their son was 19 and we got along well and would workout together in their gym.

Well, staying with them for 3 days turned into months as the application process to become a priest was quite lengthy and I had to see a psychologist, go through interviews with priests, and do a bunch of medical tests. I started to go to daily mass with this nice Catholic lady and the priests at the Archdiocese of Philadelphia wanted me to apply there, so I did. Their psychological tests were much more intense than the Pauline Fathers. It was a three day psychological test, which included an IQ test. I was nervous about going to seminary in Poland, so decided to focus on staying in PA.

I was still talking to Jane throughout this process, but she still did not want to get back together. I had a final interview with the Archdiocese of Philadelphia in a large roundtable discussion with a bishop and about 5 priests, who discussed my application and 10 page essay. The Vocation Director said I was accepted to St. Charles Borromeo Seminary and I would start in the fall. The final step was a rubber stamp by the Cardinal to accept me. Well, the Cardinal did not rubber stamp my application and weeks before I was supposed to start seminary, I was rejected. The Cardinal said I needed another year of discernment to make sure I was on the right path. 

I was devastated. I cashed out my 401K and decided to make steps to move to Italy. If I was going to discern, I wanted to go to the heart of the Catholic church and be in Italy. Initially I thought about moving to Rome, but then decided to go to Lake Como as I heard it was nice. I booked a ticket to Zurich from Philly and booked a first class train ticket to Lake Como. I was scheduled to leave that week. 

I talked on the phone to Jane about my journey and she said she didn't want me to leave. I said "so you want to get back together?" She said no. I said, fine then I am leaving and moving to Italy. My last day in the US, I booked a room at the Philly airport Hyatt and Jane called me and said she wasn't willing to let me go to Italy and took a bus from NYC and stopped me from flying to Zurich. We had the most incredible make up sex at the Hyatt that night and it felt so bad as pre-marital sex is a sin, but oh it felt so good too. 

We had dinner at the hotel that night and I said "are we back together?" She said "idk." Confusing. I said "so am I catching a flight to Zurich in the morning." She said "idk." Typical 21 year old. Acts first, decides later. So I said "well I want to be with you, do you want me to come back with you to NYC in the morning?" She said yes. I had moved out of my old place and temporarily moved in with her at her new place at another spot in the East Village. At first, it was amazing to be back together. But, then we fought. Oh we fought like in the Notebook. I don't even know what we fought about, but we were pissing each other off. 

She ended up getting a new place in the East Village on 7th street and I got a place on 9th street. 2 blocks from each other. We were surviving, but were not in an official relationship and were just FWB and I didn't like that. Eventually we broke up for good and I never saw her or heard from her again. 

The End. 

- Isaiah

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 
Just.Lurking.Ghost_Scrutinizer

Hey Isaiah

I had to create an account just to respond to you after reading your post. I remember seeing one of your comments back in 2023 or early 2024, where you mentioned a mother who was willing to help you land a job in private equity just to keep you with her daughter. That comment really stuck with me, and now, reading the full story from start to finish, I’m absolutely blown away.

It’s such a fascinating yet deeply heartbreaking story. Seeing all the details now, it feels almost surreal how everything played out. Honestly, this is exactly the kind of content that keeps me coming back to this site from time to time. Stories like this—raw, human, and full of emotion—are what make this platform so unique.

That being said, after learning the entire story, I have to admit it really pinched my heart. Sometimes, knowing everything makes it even harder. Thank you for sharing your journey so openly. Take care of yourself, and I hope the best for you in whatever comes next.

Thanks bro. Yeah, like they say in the movie 21, it was a life experience. I appreciate you coming back and posting - thanks for being a part of the community as well.

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

Isaiah Yet again showing his is the most interesting man alive. What a story man.

 

"...I talked on the phone to Jane about my journey and she said she didn't want me to leave. I said "so you want to get back together?" She said no. I said, fine then I am leaving and moving to Italy..."

What a story. Was hoping for the happy ever after when you wanted to leave to devote yourself to a higher power and move to Italy, she didn't want you to leave....but also didn't want you to 'stay'. Wtf girl make up your mind. 

Kind of crazy how you went through all of this shit, just for her say idk, but good on you either way. 

You can catch flies with honey, but you can catch more honeys looking fly
 
GordonGekko87

That’s a fucking movie. You’ve had a life, haven’t you? Respect man.

Yeah man, have had a lot and this week is one of the most intense weeks I have ever experienced. Either going to an MBA program in one state or moving to California if I don't get in. I have a massive amount of art and books and need to figure out what to do with everything.

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

Your story reads like a script for a movie. The part about the bipolar hits hard for me especially as I can relate, thank you for sharing my friend

 
monkeybiz03

Your story reads like a script for a movie. The part about the bipolar hits hard for me especially as I can relate, thank you for sharing my friend

Thanks bro I'm interested in screenwriting and have proofed scripts before for friends in screenwriting school in NYC. I want to write a screenplay one day. I'm not sure if it would be a fiction, non-fiction, or autobiography.

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

What an incredible story, thanks for sharing. It is mind-blowing just how much of an impact certain people can have on our lives. I've got my fingers crossed for you to find the right Jane, because you are overdue.

Finding the right person to go through life with was the single greatest blessing I've experienced and I wish I could tell you I had some great strategic plan that was foolproof, but it was just complete luck. Met my now wife at a party and I know it sounds like BS but it felt like my life really just began once our relationship started. You can call it corny or exaggerated, but years later, that's still how I look at it. Perhaps the one piece of advice I would recommend is leaving no stone unturned. There were only two women I ever really had a strong and special connection with, and I wouldn't have really guessed either of them to be my type. For example, you're an exercise nut and fairly religious, no? Well don't be afraid to go out on a few dates with an agnostic girl who never really cared for the gym. Hope its not overstepping, just want the best for you mate. 

 
Deal Team Six

What an incredible story, thanks for sharing. It is mind-blowing just how much of an impact certain people can have on our lives. I've got my fingers crossed for you to find the right Jane, because you are overdue.

Finding the right person to go through life with was the single greatest blessing I've experienced and I wish I could tell you I had some great strategic plan that was foolproof, but it was just complete luck. Met my now wife at a party and I know it sounds like BS but it felt like my life really just began once our relationship started. You can call it corny or exaggerated, but years later, that's still how I look at it. Perhaps the one piece of advice I would recommend is leaving no stone unturned. There were only two women I ever really had a strong and special connection with, and I wouldn't have really guessed either of them to be my type. For example, you're an exercise nut and fairly religious, no? Well don't be afraid to go out on a few dates with an agnostic girl who never really cared for the gym. Hope its not overstepping, just want the best for you mate. 

Thanks bro. I am starting a Full Time MBA program this year and feel I will meet some quality girls there. I'm looking forward to it. Congrats to you on meeting your soul mate. 

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

You are me 3.5 years ago. I was 21 pushing 22 when she called it the end of the road. She was great, and we were together for 4.5 years and we always talked about going all the way. It was unexpected, no doubt. Separating completely derailed my life plans.

My best advice: work on yourself and keep doing your thing. The world keeps turning even when shitty things happen to you, don’t let it be your downfall.

I’ve looked back on that moment as a blessing because it was the first domino that fell of many that ended up changing my life. I got in better shape than I was in HS, left the public sector for a career I love, and moved out of my hometown that had very little to offer to a gateway market in my profession.

You’ll find someone eventually; in the meantime, polish yourself as an individual and you’ll find someone better than you had, TRUST

Best of luck Player.

 

Throwaway account because this is really personal, but I’m a 22yr old senior and I went through this when I was 20 the summer after sophomore year.

Wasn’t that great with the ladies in high school and used it as fuel to keep grinding to get out of my small-minded environment and get to a target school and find a girl that understood me on all levels..intellectually, socially, spiritually, etc. 

Fast forward to the spring of my sophomore year when I finally thought I had life made, I secured an internship for junior summer at a top bank, was in the best shape of my life, and was killing it in school and confident in all areas of life, including women.

I had a situationship with this girl that entire semester and finally found someone I could fully be myself with, was beautiful, and had the exact background and values I wanted; she was the first girl that told me she loved me and the first girl I ever loved and saw a real future with.

Unfortunately, I had too rosy of an assessment of the situation and she ended up cutting me off to go back to her high school sweetheart right after I flew halfway across the county for her birthday. This was after her telling me how toxic he was and how poorly he treated her, and promising me I never had to worry about him (I know the classic red flag response right).

The following weeks were my lowest point in life, I had an intense period of self-reflection as I was living alone 1000 miles away from friends and family in a city where I knew no one merely for a corporate internship that looked good on a resume but did not excite me.

I realized how much of my life’s motivations and ambitions came from external validation and some insecurities from when I was younger instead of pursuing my passions unbridled by societal expectations or norms. I also got in a bad comparison mindset to the ex-boyfriend who was out of shape, didn’t attend college, and seemed like a horrible partner for her, and asked myself why I grinded so hard for six-pack abs, a top school, and top internships when I’m going to lose like this to someone who was the antithesis of everything I strived for. I realized I was too prideful and conceited to lower my expectations or think she could leave for him, and reality slapped me in the face real solid.

My advice to you is to prioritize your self-worth in a way that I still haven’t. I still deeply care about this girl and can’t find a way to cut her off for good. She spun back on me after my semester abroad and still texts, calls, and FaceTimes and I still answer just for the chance to spend time with her again before we graduate.
 

P.S. Don’t put too much expectations on finding a replacement, I’ve gotten with a dozen girls since and none of them stun me in my soul the way she did, but I’m sure as time goes on, things will work out and we will find the best partner for us that will drop anything for a future with us. 
 

Keep your head up brother.

 

I've got a story so similar to this. I absolutely fell in love with a girl freshman year. Hell, before freshman year we started talking a lot as we were going to the same Uni and we met online. That turned into us FaceTiming every night for the whole summer before we even met each other. Then, I moved into my dorm a week early because I was apart of some early class program. She drove down 4 hours to see me even though she wasn't moving in for another week. That was the point where I knew I was in love with her. That gesture was incredible for me...that turned into a 3 year relationship with half a year of living together. Half of that relationship was dating, the other half we were on and off. I think we fell out of love about a year in. I got bored to be honest...I had made her out to be this incredible person and constantly put her on a pedestal but I ignored her flaws. God, I fell so hard for her and didn't know how to process my emotions when I slowly started to realize I wasn't in love with her. That led to a lot of pain on both sides. Anyways, fast forward to now and still I have yet to meet anyone that I would date. No one has, as you said "touched my soul" the way she did. To this day I love her. I am not in love with her and don't want anything to do with her but I think I will always love her. She is a part of me, going through so many fundamental life-changing experiences with her as my partner. To make things worse, I think dating in our generation is so fucked...I don't really know how I am ever going to trust anyone enough to let myself fall in love again. Especially with graduation looming and an IB job looming...I guess I'll just have to keep figuring it out. 

 
Mr. Disagreeable

My GF just left me because I bought a Patek instead of giving the money to charity

(ngl the patek was worth it)

I met a girl at The Standard NYC and was wearing this chromed out Gucci G watch that Manny Fresh wore in the Big Tymers "Still Fly" video, and she said "I like your watch, but prefer Patek's." I said "Do you know how much Patek's cost?" She said "Yes, and that's why I like them." 

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 
earthwalker7

You will find someone else.

Seriously. Heartbreak sucks. Life goes on. 

You can chose to be miserable going forward or you can chose not to be. 

Commercial Real Estate Developer
 

“We are smart enough not to buy into the oldest myth running, love. Fiction created by people to keep them from jumping out of windows”. In all seriousness though that’s a great adage, I look forward to what’s to come and my biggest priority at this point is realizing how much I changed for the better as a result of our relationship

 
GordonGekko87

There’s a reason a windshield is larger than the rear-view mirror;

Aerodynamics? 

Commercial Real Estate Developer
 

Quant/Nerd lost his true love. I’m going through a similar thing.

Long story short, had a huge crush in someone in year below, asked her out after I graduated from university, was in talking stage, didn’t get a return from my internship, fell into severe anxiety and depression. Said to her I couldn’t do this anymore, some issues in communication, she lost romantic interest, it was all my fault.

It’s been 3 months since it happened and honestly she is the greatest person I’ve ever met. I still look at her instagram, listen to romantic songs, watch romantic movies wishing it was her and I.

I used to glorify the industry but honestly I fucking hate it now, it’s made me lose so much, and this relationship made me realise. At the end of the day, in the situation I was, I wouldn’t have wanted to go out with myself either over the past few months. I hope she’s happy and being treated correctly, and I don’t want to forget her because she’s so great.

I understand your pain. I talked to a therapist and one advice that’s worked for me is to be okay to be sad, and its okay to lament what’s happened, because if the persons easy to forget or let go off then they probably weren’t the right/great person anyway.

 

Gonna get MS for this but I don’t care. You need to stop reminiscing so hard. You broke it off for a reason. Even if you want to say that your thinking was not rational at the time, you aren’t a stupid person. Stop thinking back to what didn’t happen and focus on making the present a gift to your future self.

You didn’t get a return offer and that crushed you. The smartest people I know take failure really badly because they are used to winning without breaking a sweat. If you want true, enduring success in life then you need to take away the key lessons from both your internship and failed relationship, and MOVE ON to a new company and a new girl. Best of luck man :)

 

for me to begin to move on i first had to recognize that we weren’t together anymore because she didn’t want to be in the relationship.

it sounds obvious but it was very hard for me to accept that she didn’t want to be with me anymore, and that was an unchangeable fact

think about everything you bring to a relationship, you are (probably) a really cool person, maybe even a remarkable kind thoughtful loving person. you deserve someone who wants to be with you deeply

 

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