5 Breakup Stories That Will Make You Cry
Five stories of love that didn’t quite make it.
By Kelly Bourdet, Refinery29
Our past relationships — from the high-school boy who dropped us after two weeks to the “the one” who broke our heart — shaped us permanently. The exes who were unfaithful left us afraid to trust someone new. The exes who loved us exactly as we were helped us to accept ourselves more fully. The exes who left us taught us how to let go, and the exes we outgrew taught us how to to leave someone you haven’t stopped loving.
In a sense, we love everyone we’ve ever loved — they’ve imprinted on us and shifted how we approach the world. If they had our hearts once, then they changed our hearts for good. So, we bring you five stories of love that didn’t quite make it.
Malory, Fashion Director (left)
Zoe, Retail Planner (right)
How long were you two together?
Zoe: “We dated for two-and-a-half years-ish.
And, how did you break up?
Zoe: “We were breaking up for probably like a six-month period about a year and a half ago.”
Malory: “And, then I broke up with her, but I kept coming after her. Finally, she was just like, ‘No more.’ She cut me off.”
Zoe: “Yeah. She broke up with me, but we were still hooking up. It was just not what I wanted. So, I was just like, ‘Fuck yourself — it’s time for me to move on.’ Then she started dating other people.
Was there a time during your relationship when you weren’t getting along?
Malory: “We fought a lot. We’re alpha females.”
Zoe: “I think that was part of the problem with our relationship — there were a lot of times when we were not getting along. A lot of bickering, about stupid shit.
Why did you break up?
Zoe: “I think we were just sick of it. We just clash.”
Malory: “I don’t respond well to excessive emotion. She would cry and get upset.”
Can you tell us a little bit about how you met?
Malory: “I was the other woman.”
Zoe: “In college, I was hooking up with this guy. His name was Dan.”
Malory: “He was hooking up with me on the side. He was a serial cheater.”
Zoe: “He was cheating on me with her, and he used to cry about how much he loved me to her. But, then we pledged the same sorority. We hung out a few times, but we never did anything.”
You hung out as friends?
Malory: “Yeah, it’s just kind of awkward and hard to say, ‘Are you a lesbian? I might be a lesbian.’”
Zoe: “She actually sent me a text message. We hung out one night, and I wasn’t brave enough to do anything. I went back to my room, and she sent me a text message that said, ‘Come kiss me.’”
You two seem really close now.
Zoe: “Well, about eight months ago, I was diagnosed with cancer, and that completely changed our dynamic.”
Malory: “We became best friends.”
Zoe: “I was possibly on the verge of death, and I think that you really reassess your relationships with the people that you’ve loved when something like that happens.”
So, Malory, you helped Zoe when she was going through her health struggles?
Malory: “I slept in a chair in the hospital.”
Zoe: “Yeah, I was in the hospital for a week, and she stayed with me almost every night. I think it was almost an opportunity for her to fill a role that was never really there for her before. It really gave us another level to our relationship that I don’t think was there before.”
Malory: “She’s such a tough chick, you know? She’s never the weak one. It was always me.”
Raven, social worker (right)
Matias, artist (left)
When did you two meet?
Raven: “We met almost two years ago — June? We dated for six months.”
How did you meet?
Raven: “At a friend’s gallery.”
What was it like in the beginning of your relationship? Anything stand out as great?
Raven: “No. It was just a hot mess. The whole thing. He was just really drunk and fucked up, and we were like, “This is a good idea.” And, it wasn’t. I don’t know. Sometimes you meet people and you’re supposed to be friends, not date each other.”
So, why would you say you broke up?
Matias: “Well, I used to have a big drug problem. So, I got sober, and I kind of pushed away everybody in my life, including Raven. She was very understanding.
Raven: “I’m about six and a half years sober, so I needed to let him do that. We didn’t talk for almost a year, but we became friends again this year.”
So your drug use came between you?
Matias: “I was doing everything that was addictive behavior, including our relationship. It was always back and forth, like, ‘I want you, I want you not.’”
Raven: “Like , ‘I want you, I don’t want you.’ And, I’m like, ‘This is terrible. This is the awesome…No, it’s a terrible, terrible idea. No, it’s cool — I can stay with you…’ Very healthy! Super healthy and not codependent in any way whatsoever. Yeah, it was the opposite of that.”
Was there a final straw? Or did you slowly drift off because of what was going on in your life at that time?
Matias: “Well, really fast, it started to…”
Raven: “Yeah, it got nasty. Just fighting and the push and pull with Matias. He was all over the place. There was not a lot of consistency there.”
Matias, can you say what was your favorite thing about Raven?
Matias: “She’s really funny. She’s very nice; she’s great. She doesn’t take herself seriously, and we laugh a lot. The thing is, we’re great friends. We laugh, we talk shit, and just do our thing. And, we’re happy about it.”
Raven: “We’ve watched porn comically.” [Laughter.]
Matias: “Just commenting.”
Raven: “Yeah, commenting like, ‘What the fuck is that?’ and feeling nothing.”
Sounds like a great friend activity in the afternoon, porn watching.
Matias: “Sunday morning.”
Raven, what do you love about him today as your friend?
Raven: “He is brutally honest and very caring. I feel like if I ask Matias for an opinion, he will tell me the truth. Not what I wanna hear. It’s not like with a girlfriend or other male friends. It’s just that brutal honesty that happens when somebody cares about you and isn’t trying to get something out of you. And, I know Matias is not trying to get anything out of me.”
Tommy, photographer (left)
Emily, fashion stylist (right)
How did you met?
Tommy: “We met in 2005 or 2006.”
Emily: “We met through mutual friends.”
And, how long did you date?
Tommy: “Five years? Six years? It was kind of off and on.”
So, how did you ultimately break up?
Emily: “We broke up in 2010 for the second and last time. We sort of had two distinct relationships.”
Which was the better relationship?
Emily: “I think the second one.”
Tommy: “It was shorter.”
Emily: “The decline was exponential in the second one.”
Tommy: “For me, it was like the sequel. But, sometimes sequels are exactly the same as the first time around.”
Why do you think you broke up?
Emily: “For me, codependency. I think we stopped being our own people.”
Tommy: “That’s true. But, I think that as I get further away from the relationship, I see it less as codependency and more as simply being young and immature and not being a fully formed human yet.
You guys work together professionally now, and Emily, you have a boyfriend. How does this work with your current relationship?
Emily: “Everything is really good with my relationship right now, and I’ve learned a lot about myself. It’s the best relationship that I’ve ever been in, and I owe a lot of that to my relationship with Tommy, because we both worked really hard to iron-out some of the issues that we had. And, I was able to kind of use him as practice, in a fucked-up way, for a healthy relationship. I think we both learned a lot from it.
Tommy: “You’re tearing up over there.”
Are you okay?
Emily: “Breaking up with Tommy was, to be honest, the hardest thing I’ve ever done in my life. When we broke up, I thought I was going to die. I didn’t think I would be able to survive without him. And, now, I think it was the best thing that ever happened to me.
My relationship right now is amazing. I’m engaged, and I have a partner that is dedicated to me and dedicated to his own growth and health. And, that’s his own journey, and I see my own growth as part of my own personal journey. With Tommy, I couldn’t see myself as growing without him.”
Tommy: “Yeah, our breakup was the hardest thing I’ve ever had to do. But, I think I came away fully formed and independent. But, I learned a lot from it. And, our relationship continues to shape my identity even today, but in positive ways.”
Tommy, what is your favorite thing about Emily?
Tommy: “Wow, it’s hard to choose. She’s just fully unique. She’s really interesting as a person. I like how loud and obnoxious we can be together. I’ve just never known anybody else like Emily.”
And, Emily, what do you really like about Tommy?
Emily: I really appreciate Tommy’s vision. I think he’s really creative. He used to do this thing when we were dating that used to really bother me, which is that he listens a little bit and then he stares off into space. We fought about it. And, one day I asked him why he did that, and he said, “Oh, I’m just looking at the way the light falls on this thing.” And, it just made me appreciate how he absorbs the world and sees it in a different way than I do.
Tommy: “That’s very sweet.”
When were you happiest together?
Tommy: “Well, we had a lot of fun together in our relationship. But, in terms of respecting one another and being able to communicate clearly, I’d say right now is the happiest.”
Emily: “This, right now, is the best it’s ever been.”
Alex, consultant (left)
Ben, news editor (right)
How did you meet?
Ben: “We met my freshman year of college. I was in New York and my best friend from home went to Bard college. I went up to visit him and he took me to a party in the woods. This was 2005 or 2006, so people didn’t really have cell phones. My friend was in a fight with his girlfriend, and he left me alone to go call her from a landline somewhere. I was just there with a bunch of people I didn’t know very well. And, eventually, Alex came up and said, ‘Hey, you look lost.’”
Alex: “We had met briefly before that.”
Ben: “I guess we ended up drinking a jug of cheap red wine. And, then we went back to Alex’s house, and then — cut scene — it’s the next morning. And, we had ‘met’ each other. That’s the PG-13 version.”
How long were you were romantically involved?
Alex: “It was like four or five months.”
Ben: “After that, we kind of were seeing each other…”
Alex: “It was tricky because you were at Columbia, and I was at Bard, and it was a weird thing to try to date. It involved all this logistical planning for this guy that I was not in a committed relationship with. So, I just felt that it seemed like a lot of work. But, it was fun.”
How did you guys break up?
Ben: “I started dating someone else. I think it was kind of like a fade away…like, we both stopped answering calls.”
Alex: “It was not a contentious breakup. We were busy at school. It was just a casual thing that drifted and then fell off. But, then we were both interning in New York City the following summer, and we became friends. We got really, really wasted together at a beer garden, and I just realized, ‘You’re really fun.’”
And, you just kept hanging out as buddies?
Ben: “Yes, we’ve been really close friends for five or six years.”
Alex, what’s your favorite thing about Ben?
Alex: “I have a weird sense of humor that no one gets better than Ben does. I think I probably knew that from the beginning — it was the most appealing thing about him.”
Ben, what’s your favorite thing about Alex?
Ben: “I almost don’t know what to say. He’s just a good friend in a very traditional way. Just, like, sweet. Good at taking care of people. Good social graces. And, we always have a lot of fun together. It’s easy, and we have a good time. My fiance likes him.”
Oh, you’re getting married?
Ben: “Yep, I just got engaged.”
Alex: “And, I get to plan his bachelor party for him, which is awesome. First we’re going to New Orleans in April, just the two of us, for a ‘pre-bachelor party.’ And, then we’ll figure out what he wants to do for the ‘real bachelor party.”
Michael, producer (right)
Chelsee, marketing associate (left)
How long did you guys date?
Michael: “About a year..ish? There’s never really an official beginning or end.”
How did you meet?
Michael: “OkCupid!”
What was the first date you went on together?
Michael: “Oh yeah, it was June…maybe? Whenever it was, it was during that time when it was raining constantly. There was an entire week when it just would not stop pouring rain, and we went to some stupid bar in Greenpoint.”
Chelsee: “It was fine. It just had expensive drinks.”
Michael: “It’s the most twee bar on the planet — it sucked.”
Chelsee: “It wasn’t that bad.”
Well, it was a good date though, right?
Michael: “The first thing she said to me when she walked in the door was, ‘Are you a lucky person?’”
And, what did you say?
Michael: “I said, ‘Yeah!’”
Chelsee: “It was because it had stopped raining!”
Michael: “Oh, that’s why?”
Chelsee: “Yes, when I left, it was raining. But, right when you arrived, it stopped raining.”
So why do you think you were able to maintain a friendship after dating romantically? Not everybody is able to do that.
Michael: “Because we like to do fun, weird stuff.”
Chelsee : “And, I think when you have a connection with someone, I don’t think it necessarily goes away because the relationship didn’t work.”
Michael: “Yeah, and we’re both really focused on making sure we are friends.”
That brings up the ultimate question in this series, which is: Why don’t you think it worked out?
Michael: “We’re both really stubborn. We’re both profoundly stubborn. And, I don’t think you can have two really stubborn people, two magnets facing in the same way…” Chelsee : “Yeah, it’s the same push of the magnet.”
