Alexandra Lee on Her First Heartbreak + Learning to Let Go



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Alexandra Lee makes things happen. As the Director of Business Development at Crush + Lovelyshe forges creative and technology partnerships with for-purpose organizations and companies. As a lover of the arts, she is an active member of her alma mater’s Friends of Art Committee. She splits her time between Brooklyn and San Francisco, where you can usually find her on a run or deep in conversation over coffee, using lots of hand motions. 

ON HER FIRST HEARTBREAK
“The first person to break my heart was my first serious college boyfriend. He was an incredibly charming, intelligent, and attractive guy and I was head over heels from the word, ‘Go!’ I’d fallen for him when we were both working for summer camps in Boston and although we dated for just a few months, I remember thinking, ‘this is the guy I’m supposed to be with.' He also had a wonderfully warm and welcoming family and in the way that you do when you’re 18 - or maybe just the way I did - you paint your entire life with this person WAY too quickly. It’s so embarrassing to think about now. I remember him calling me to break it off. I was on my way out with some friends to grab dinner and he very gently ended it over the phone. I sobbed in the parking lot - the really unattractive, snot rendering kind of sobbing. The kind of crying that makes you feel like a crazy person, but also the kind of crying that you look back on and realize that those tears weren’t for him but for this ‘plan’ you had for yourself that wasn’t really the truth of things."

TRYING TO MAKE IT WORK + BECOMING FRIENDS
“After I stopped crying, I spent a few weeks tormenting him with emails about why I thought it could actually work. He was really kind and wrote me back beautiful messages (which I, in turn, misinterpreted as hopeful), but really he was just being a nice guy who didn’t want to hurt me. Amazingly, we got back to just being good friends after that. I’m still in touch with him (and his amazing family) and I even got invited to his wedding! So clearly, broken hearts heal and, with time, I was able to see him for who he really was to me - a dear friend with a big heart.”

WHAT SHE WOULD TELL HER COLLEGE SELF
“I’d tell myself to honestly look at the relationship and consider if I was getting what I needed and deserved at the time, not just if it looked like the relationship I wanted. I remember being so wrapped up in this world I wanted to be part of - and that relationship was tied so tightly to my notion of ‘fitting in’ and ‘being part’ of the idea of something that I wanted - but it really wasn’t me. There was a lot of good too, don’t get me wrong, but I’d definitely tell myself that I deserved more than what I was getting."

Alexlee Laptop

Alexlee Writing

ON HER MOST RECENT HEARTBREAK
“I broke my own heart and the heart of a guy that I spent many, many years with - but it wasn’t right. I don’t even know how to explain it. I just knew it wasn’t the relationship that I wanted to be in the rest of my life. I’m incredibly lucky to have an amazing family and an incredibly supportive group of close women friends. My lady crew in particular were rock solid for me in the months following that breakup. More than giving me advice, they just made observations about me and the way I was behaving - that I seemed happier, that I was more willing to be out and about, that laughs were faster to come and I was smiling more, and just seemed more at ease. They never directly commented on whether they thought ending the relationship was ‘good’ or ‘bad’ - they just sat with me through it. At the time, I was also training for a half marathon and there was this one life-changing run across the Brooklyn Bridge where pieces of my life came together. So long stretches of physical movement helped me a lot.”

LETTING GO OF WANTING TO CHANGE THINGS
“I truly believed that I could make it hurt less for my ex, but he had and continues to have his own experience and emotions around the breakup and I can’t do anything about that. For a few months I thought I could help him see why the breakup was good - but that wasn’t my right. The Executive Director of a great non-profit in Texas says this thing: ‘When we want something for someone more than they want it for themselves, it’s not help; it’s an act of aggression’ - and I come back to that over and over again. I wanted something for my ex during the relationship, and after - but it wasn’t my call to make. I had to give that up and let him live his life.”

Alexlee Brickwall

Alexlee Laughing

HER BREAKUP VICE
“I didn’t take any time to breathe after my last breakup - I just started sprinting after everything without giving myself an opportunity to sit with it for just a few minutes. I’m not sure I really conquered it, but at some point I started to allow myself to slow down.”

HER BREAKUP RITUALS
“Three things: cut hair (it really does feel that good), go on a solo vacation (preferably without cell phone reception), and write letters to yourself and then delete them. You have to process some ugly thoughts about yourself and you need to get them out but never re-read them. Never.”

HER FAVORITE SONG ABOUT HEARTBREAK
"Bonnie Raitt - Can’t Make You Love Me”

THE MISSING PIECE
“I think love and heartbreak are so personal, there’s really no advice to give - I think in all instances you just have to remember to be kind to yourself and to be kind to your partner (or ex partner). I will say that Shel Silverstein’s ‘The Missing Piece Meets the Big O’ is the greatest love story ever told though. The possibility of finding someone who truly supports and understands me, and vice versa...that seems like an adventure worth committing to over and over again.”

Photography by Elena Kulikova.