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Boston.com readers share their breakup stories

This Valentine’s Day, we asked Boston.com readers to share their love stories and breakup stories with us.

What follows are the tales of love that, unfortunately, did not work out.

A major move, and then a move back

“I am born and raised in Arlington, lived most of my life in the area. After dating a woman for about a year, when I was in my late 20s, she proposed moving to Phoenix together, getting married, while we spend about 3-years out there together. I hadn’t previously thought about moving out of Mass., but I thought she was worth the adventure. After she also planned out our wedding on paper, I thought this was a pretty decent lock. So we packed up in August of 2003 and went. On the 3rd day of moving into our new apartment, after a 4-day road-trip, she drops to the floor and starts crying. When I asked what was wrong, she opened up that she no longer wanted to be in the relationship. I asked how long she had felt this way, and she said for about a couple weeks. Would have been nice to have known that before we made the trip. So I packed up my Jeep the next day and left, moving up to Boulder, Colorado (where a close friend was living) as I had no intention of staying in Phoenix (no offense AZ). I won’t deny I was a little hurt by this sudden change of heart, but after growing up in Mass., Arizona was definitely not the place for me, so leaving wasn’t that difficult. I spent 3 years in Boulder and then eventually moved back to Mass. End of story.” —Anonymous

Movie date gone awry

“It’s 1976. I’m dating a cute-as-a-button young lady named Tai. We’d been going out for a few weeks, and sorta made it a regular Friday night thing to see an early movie, then party hop. This one Friday we’d agreed to see the new, critically-acclaimed Network at our local Cineplex. We get there, and while we’re waiting in line for tickets Tai bleats ‘Oh Wow! Look! Saturday Night Fever’s playing here! Let’s see that instead!’

In 1976, there were two kinds of teenagers: Those who really, really, REALLY liked Disco music, and those who really, really, REALLY did not. I did not. Really. But…being the gentleman my Irish mother raised me to be, I bought us two tickets to Saturday Night Fever. Two hours of fingernails down the chalkboard ensued. We had a long, quiet ride back to her house, as I made some excuse about not feeling well or something. Not far from the truth, actually. Afterward, I hit one of the usual Friday night house parties. My friend Raymond, our host, asked about Tai, and also if I was feeling all right.

‘Long story, man. Say, could you put some Hendrix on the turntable?’” —Art Cestaro

“It hits me like a bulldozer”

“We fell in love and we got married and my business was growing year after year but, I traveled a lot. And I mean a lot. I was flying all over the country as a corporate photographer for a healthcare company. I come home one Friday night from one of my photo shoots with a pizza and a six pack of beer and she is sitting at my desk in my office and I can see right away that she is very upset. The first thing I think of is her grandma or someone in one of our families is hurt. I ask her what is the matter and she looks at me and says a guy at work died yesterday. I’m thinking, oh that’s terrible but, so people die all the time why is she acting this way? And then it hits me like a bulldozer. This dead guy was her boyfriend.” —Anonymous

A breakup haiku

Went through my iPhone
Saw messages from past loves
Spoke of hurt and pain then *poof*


“She said we should remain friends, but I wasn’t interested in that”

It only took a week. I met a great woman (pseudonym “Jill”) on Bumble in April 2019. We had a first date, which I thought was great. Later when I suggested a second date, she said she was only interested in something platonic. I was a bit disappointed, but I went with it. Over the next six months, we became close friends, getting together about twice a week for drinks, food, hikes, etc. Then on Halloween she had me join her for a friend’s party. When I dropped her off at her home afterwards, she had me in and said “I think we should try dating.” I was thrilled. So we spent much of the next four days together. The next day after work I went to her home just after she learned a family member had died suddenly. This was not a first-degree relative, but one who Jill was very fond of, so she was quite upset. I thought I was being properly supportive as she processed this loss. Then we didn’t communicate other than a few texts for a couple of days, and then she went on a pre-scheduled weekend with friends on the Cape. When she returned I called her, and she said that she decided our relationship wasn’t going to work. The only reason cited was that I didn’t properly “lift her up” after she heard of the death in her family. What was I supposed to do, say forget about it, it’s no big deal, let’s go to a party? I think that’s how you support someone who has had a bad day at work – not someone who is experiencing grief.  (As a side note, Jill and I are not immature; we’re both in our 40s). I expressed my disappointment with her reaching this conclusion after having been together as a “couple” for only a week, and stated my view that we still could be great together, but she was set in her decision. Very disappointing. She said we should remain friends, but I wasn’t interested in that, so we have not been in contact. —Anonymous

Responses have been lightly edited for clarity.


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