Hit The Road: People Share Their Terrible Vacation Breakup Stories

September 10, 2023 | Miles Brucker

Hit The Road: People Share Their Terrible Vacation Breakup Stories

Vacation is a time to unwind and relax. Being in a new city or country helps us gain perspective and can provide us with new insight about our lives back home. If you have someone special in your life, naturally it makes sense to go on a trip together. You want to deepen your relationship and have an adventure, right? This makes sense in theory, but couples sometimes find that the stress of travel is too much for their relationship to handle. The big problem is, once you are out there you usually have to finish your trip together before you can go home and unpack the “baggage.” Here are twenty-five vacation break up stories that show just because you love someone doesn’t mean you can travel with them.

1. Talk About Fantastic Timing

I was 16 and totally head over heels for my best friend since I was 8. He felt the same way, we long-distance dated for about 8 months. Before going on a trip to Italy, I call him and he seems distant on the phone. I chalk it up to stress or whatever and go to Italy promising to bring him back something great. I spend the whole trip wearing the gaudy dolphin necklace he gave me and spent an insane amount of money on a Ferrari remote-controlled car at the Ferrari HQ.

I come back from my trip, call his house, and his dad answers. I ask to speak to my boyfriend, and he says “Oh, he told everyone you guys broke up before your trip.” I gave the car to my little cousin.


2. Talk About An Emotional Rollercoaster

My boyfriend and I were long distance. I paid for him to fly down and visit me for two weeks. On the second or third day of his visit, my grandfather passed on. I was an emotional wreck. The next day he broke up with me on account of me being an emotional rollercoaster, then got mad when I said he couldn’t stay with me the rest of the visit.

He then claimed he didn’t mean what he’d said about breaking up, then broke up with me again as soon as he was back home.

Snobbiest Behavior factsShutterstock

3. A Little TOO Curious

I have two children from a previous marriage, and we have one child together. I went home (another country) to see my eldest son graduate. My spouse, who bitterly hated it when I traveled and he couldn’t go, urged me to “take some time, see your friends.” Historically it had been anger before I left, anger when I was gone, and anger when I got home. He had been unemployed for nine years and was totally dependent on me.
He wanted for nothing: every new toy, new computer, new car, new laptop, and all the new games, which he spent hours mastering. It was a pleasant surprise to be offered a bit of time with no guilt. He seemed interested in my son’s graduation: the day, the time, and I honestly thought nothing of it. It felt good. On the day my son graduated, as we were standing outside for the pictures, my ex texted me from 1,700 miles away. What I read made my blood run cold. 
He'd written: “I want a divorce.” I was a zombie. Posing for pictures, mentally re-arranging travel plans to be completed as soon as my son’s celebratory party was done. I return home and the house had been ransacked: furniture, books, etc., missing. It looked like a tornado had gone through the living room. No note. No address. Nothing.

Vacation Break Up Stories FactsShutterstock

4. That Will Cause Some Turbulence

A friend of mine broke up with his girlfriend of two-and-a-half years, while on a plane to a wedding in which she only knew him. They shared the hotel room for three days and sat next to each other on the flight back.

Vacation Break Up Stories FactsPxHere

5. The Beach

A friend of mine takes his live-in girlfriend to Greece for vacation. On the beach one day, he pulls out a ring and asks her to marry him. She tells him not to be so silly, she’s never going to marry him and tells him to put the ring away so they could enjoy their vacation. He sat on beach with her for two more weeks before flying back home. That’s when they finally broke up.

Vacation Break Up Stories FactsPxHere

6. Something Was Definitely Up

I encouraged my ex-girlfriend to apply (and helped write/edit her entry essay) to go to a symposium in a foreign country because it would look great on her resume and be good for her master’s degree. She gets to said country and a few days into her trip she just stops talking to me. I knew something was up. I could feel it in my heart.

She finally gets back to me and proceeds to blame me for the past three years of our relationship for everything that has ever gone wrong and make me feel like I never made her happy the whole time we were together. This goes on for a few weeks and she wouldn’t admit to doing anything on her trip. Finally, I tell her, “It’s obvious we’re broken up but are you seeing someone during your trip?”

Her answer: “Well, yes and no. But that’s not the reason we’re breaking up!”

Worst Blind Date FactsShutterstock

7. Not In The City Of Love!

My father-in-law had a girlfriend break up with him in Paris. On Valentine’s Day. And they still had to fly back to the US sitting next to each other on the plane.

Vacation Break Up Stories FactsPixabay

8. This Is Not What I Had In Mind

My girlfriend of two years and I lived together and everything. She convinced me that I should quit my job because I hated it even though I had crushing student loan debt. She buys me tickets to Voodoo Fest in New Orleans for my birthday. Instead of it being a romantic vacation for two it turns into me, her, her roommate from college, her brother, best friend from high school, best friend’s cousin, and roommate’s boyfriend.

Once in New Orleans, I run out of money very quickly and she dumps me on Bourbon Street. Instead of letting me spend the night in the hotel that we were all staying at, she graciously let me sleep in the car. Then I get to ride back nine hours to Austin in a car with her best friend from high school, the cousin, and her brother.

Now she’s married to her best friend’s cousin (the one that went with us). Did I mention that the best friend and cousin were billionaire trust fund babies?

Vacation Break Up Stories FactsWikimedia Commons, MusikAnimal

9. That Won’t Get A Like

I came back from a cruise. Everything’s normal between me and my girlfriend. We tell each other how much we missed each other while I was gone and all that mushy stuff. About three days after I got back we were talking on Facebook messenger and I decided to click on her profile and look at her pictures. I noticed that she had apparently entered a relationship with some other guy on the day I left. Unsurprisingly, she ended up cheating on that guy, too.

Vacation Break Up Stories FactsUnsplash

10. Change Of Plans

My best friend had been dating this girl for eight years. He even asked her to marry him. She wanted to wait until they were a few years older, so he agreed to wait. Fast forward about six years. My best friend, his girlfriend, and her immediate family went on vacation to Florida for a few weeks. I knew things were tense between the two of them but I just chalked it up to a dispute.

They get back from vacation, and a few days later he walks into her bedroom. I still can't believe what he said. Sits on the floor, and tells her: “I’m dumping you, I’m gay, and I’ve been dating a guy.” To make a long story short he’s still one of my best friends, but I’ve never in my life wanted to punch him so badly for what he did to his former ex-girlfriend.

Awkward Moments FactsShutterstock

11. Well, That Was Short-Lived

My ex-wife and I were on our week-long honeymoon in Jamaica. She told me the second night there that when we got back home she wanted to see other people. We definitely could’ve used the $15,000 from the wedding and honeymoon on something better.

Shortest-Lived Marriages FactsShutterstock

12. A Literal Whirlwind With No Closure

I met her at school. She was in the same year and program as I was. She joined the same newspaper that I was editing for the past year. I wasn’t looking for a relationship at the time, but after a few conversations and texts, I was absolutely enamored. We got together about two months later, and I can honestly say that it was as perfect as two people can be together.

We took a trip to New York with some friends. She got a call that she got the job she wanted in another city. I was happy for her. I had started looking in that city when I heard she was looking at the area. We took a trip to Europe, just the two of us. It needed to happen soon as her job started two months after she got the call. The trip was amazing.

I helped her pack up her things, and she drove away. We stayed in touch. I looked for a job in the area. I found one while I was at my sister’s wedding, I flew from the wedding to the interview. I stayed in her new apartment. Coincidentally, some friends of ours were coming to visit her that weekend. I got the offer letter while we were all hanging out in her living room.

Everyone seemed happy. The next day (the day all of us left) we went for lunch and hung out at the park. Great day. When everyone but me was gone, she broke the news. She wanted a break, which immediately became a breakup. I had 8 hours alone on a bus to ponder what had just happened. She had told me that she was just worried that life was changing.

I never got anything too specific, except that she needed time to sort out her life. There was a distinct impression that we might get back together after she had time to think. That was three months ago. I accepted the job because I liked the industry. I had the hope that she would come around, but I tried to remove that from my decision.

She was very evasive when I tried to talk to her (about once every 2-3 weeks). She just told me that she didn’t even want to see me to give back each other’s stuff. It’s a real punch in the gut.

Wholesome Stories FactsShutterstock

13. That’s Not Where She Saw That Going

We were dating for four years and lived together for three. I got into school about three hours away and we decided it’d be best if I moved temporarily. Everything was normal. One weekend I drove to see him and we put an offer on a house that we had been looking at and picked out floor samples. One week later he goes on a business trip and says that he “realizes our whole relationship is a lie” because he never ever wants to get married.

He gets together with a woman he met at the hotel bar, then called me up and told me. I’m pretty sure there were better ways of handling that.

Crazy Twins Stories FactsPxfuel

14. Couch Surfing For Thanksgiving

I was going to college in Michigan. She was going to college in North Carolina. We started dating in the fall and we decided that I should fly out and spend Thanksgiving with her and her family. Thanksgiving break comes and I fly out to Greensboro, North Carolina. I get to the airport and she’s not there. I call her up and she says she couldn’t make it, but to meet her at the college.

I spend what little money I had and take a taxi. The taxi driver was really nice and didn’t charge me full price, at least. So I get to the campus and she meets me at the square. We go back to her dorm and she has to sneak me in because it’s a female-only dorm. Once we get to her room she promptly breaks up with me. I spend the next couple of days holed up in her dorm room because I’ve got no way to go anywhere else.

After a couple of days, she had  her new boyfriend gave me a ride to my friend’s house. I spent Thanksgiving bouncing from couch to couch until the day of my flight.

Vacation Break Up Stories FactsUnsplash

15. You Couldn’t Have Told Me That Before?

I was visiting my family in Brazil and came back to Canada to spend New Year’s Eve with my girlfriend. Things had been a little weird for a while (we were living about 1,800 miles apart because of a school internship). I was excited to see her, but I got there and things were weird. She continued to be distant for the next three days, avoiding spending time with just me.

There was always a roommate or a friend with us. One morning we wake up and talk and she dumps me. She said she wasn’t into me anymore after over two years. My flight was a few days later and she lived in a town where I knew absolutely no one. My parents’ house was over 300 miles away, but they were outside of the country, and I didn’t have a set of keys.

I couldn’t change my flight dates, so I was stranded at my ex-girlfriend’s house for three days.

Couples Broke Up FactsShutterstock

16. You Couldn’t Wait One More Hour?

I got dumped during my father’s wake. It was a couple of hundred miles away from home. My girlfriend and I had a mild argument and she caught a taxi to the train station and went home. Within a few weeks, she was with someone else, but I only found out later. We had been together for over three years and were talking about moving in together and marriage so this news only confused and upset me further.

Plus, she had been coming to see me after I finished work and saying there was a chance we could get back together. In reality, she was using me since I was giving her money during this time. I was a doormat and she knew it.

Funerals FactsNeedpix

17. The Hits Just Kept On Coming

I was 23 years old and going on my first road trip across the country for a month and a half. My friend was supposed to go with me but at the very last minute just stopped answering my texts and calls and eventually told me he couldn’t afford it. This girl I had been seeing for two weeks offered to let me come up and stay with her before I left. After I left by myself on my road trip, she broke up with me over the phone. Somehow, it got worse. 

She never answered a single call, text, or email from me after that. A lot of this trip was me hiking by myself with just my thoughts. On the trip, I got my iPod with all my music stolen while sleeping at a rest stop in my car, and I lost my camera while hiking through Colorado, with every picture of Colorado on it. To this day it still stings a little.

Vacation Break Up Stories FactsPxHere

18. A Not So Jolly Christmas

My ex-girlfriend and I went on an around-the-world trip and when we came back home two days before Christmas, she ended our six-year relationship.

Broken christmas ornament.Getty Images

19. The Always Come Back Around

I was having a great time on vacation with a friend. My significant other was going to college four states away and I had just bought $250 worth of plane tickets to go see her (a substantial amount of money for a college freshman). She calls me on vacation and basically says she’s done. Then two months later, she comes back to our hometown, and of course, she tells me she still loves me.

I told her I didn’t want to see her or talk to her. I’m doing very well without her now. Everything works itself out with time.

Unforgettable Comments FactsShutterstock

20. Leave A Message After The Tone

My friend’s boyfriend broke up with her when she was on a family vacation. He called and left a message on their answering machine so when they all got home they hit play and her whole family heard the break-up message.

Vacation Break Up Stories FactsPixabay

21. Not So Funny At Comic-Con

I spent a lot of money on a trip to Utah for a festival and Comic-Con. Four hours before we left, I got a Facebook message that it was over and she wouldn’t be going. We had planned this for five months and had been dating for three years. I haven’t heard from her since.

Vacation Break Up Stories FactsWikimedia Commons

22. That Must Have Been A Fun Trip

My soon-to-be ex-wife went off on a weeklong vacation to Vegas on her own and then came home for the holidays. She refused to talk to me until Christmas morning. Only then did she tell me, over the phone, that she wants a divorce and I’m to evacuate our house within three days before she gets home.

Ended Relationship factsShutterstock

23. The Sound Of Silence

My friend’s ex broke up with her on a road trip (on the way to their destination). They camped out in the same tent for a weekend and then drove four hours back. She said the entire weekend was silent.

Vacation Break Up Stories FactsPxHere

24. The Seven Seas of Regret

Stuck on a cruise ship for three days after my friend proposed to his girlfriend on the first freaking day and she said no. That same first night she made out with some random guy in the hot tub. I'm honestly not sure how devastated my friend actually was, but it was intensified by the fact that he'd drink himself stupid daily by 2 pm, which would lead to him going to beg her to get back with him.

At one point, she was sitting on the new guy’s lap at the bar and he grabbed her hand and “confessed his love for her” for what must have been the fifth time in two days. It was a constant battle of trying to pull him away and convince him to either go to sleep or come with us to another part of the ship. He is a good friend, so I felt terrible for him, ‘cause that was super awful on her part and tried to help him all he would allow, but it was awful to watch.

By the end of the cruise, the entire boat it seemed like knew what had happened. When I tried to bring it up with my girlfriend (who was on the cruise with me as well) days after we got home, she straight up refused to talk about it, saying that was painful enough at the time so we never need to speak of it.

Thomas Seymour factsShutterstock

25. Disneyland Is Supposed To Be A Place Of Love

My friend had his first girlfriend and they were dating for about three months. The parents of the girl absolutely LOVED him. This girl however, didn’t really want to even hold his hand. Before I say anything let me throw this out there, this chick isn’t the brightest bulb on the Hanukkah bush, her “dream” was to become a female catholic chaplain. (You can’t do that)

So they invite him to Disneyland for a week and a half. (I think the parents did not her) They drive down there, have a bit of fun for the first day, then, out of nowhere she said, “Listen, I was praying last night and I really don’t think God wants me to have a boyfriend. I’m breaking up with you, we can still be friends though.”

My friend was absolutely infuriated, (he isn’t religious at all), he doesn’t show it though. They are still there for another 10 days and he is stuck with her. He pretty much did absolutely nothing due to the fact that he was depressed (first breakup). They finally finish that horrible vacation and eventually drive home. That’s when he decided to tell her parents.

They were angrier than she was. They started yelling at her and was an even worse car ride home. It’s been about 7 months since the breakup and he still has feelings for her. Poor guy, not only did she break up with him, she broke up with him at Disneyland.

Vacation Break Up Stories FactsUnsplash

26. Analyze That?

A friend of mine and her husband were married for about ten years. They have three children. Husband surprises her with a trip to the same resort in the Caribbean as their honeymoon. Cute, right? Not so much. On the second day of a five-day stay, he tells her he wants a divorce. Turns out he had been having an affair for five years. Also, he is a psychologist and specializes in marriage counseling.

Vacation Break Up Stories FactsUnsplash

27. Bye, Bye Baby

My girlfriend of 7 years went on vacation. When she came home, the first night she got back she said, “I don’t love you anymore, I may have never loved you. I’m going back home, can you buy me a plane ticket?” I bought her a plane ticket home the next day, best $400 I ever spent.

Vacation Break Up Stories FactsUnsplash

28. But Mom! I Want To Go To Hawaii Too!

My girlfriend from High School, and into the first couple of yrs of college, broke up with me the night before we were going on a trip to Hawaii. The trip was something that her family had invited me on. I had taken the days off work, packed everything, and then when I showed up at the house with my luggage, her mother told me that she no longer wanted me to go on the trip.

Only upside obviously is that I had not paid for the vacation. Prior to that night, I had no inclination that she was not happy.

Vacation Break Up Stories FactsUnsplash

29. Skype Breakup Anyone?

My friend was living with his girlfriend and they’d been together for a few years. He had to go to Spain on business for a few weeks. He flew over alone, and she was going to join him the second week for fun vacation stuff. While in Spain without her, he meets a girl and breaks up with his girlfriend via Skype.

Vacation Break Up Stories FactsUnsplash

30. No Extra Credits

We were young and fresh out of high school and in our first few semesters of college. She was brilliant and had suffered the wrath of her Asian parenting for years, but it allowed her to excel and she was able to attend a pretty nice college….three or four states over. I, on the other hand, did the bare minimum in school and lacked any motivation to improve.

As a result, I spent the first few semesters in a local college. This was good, because I finally got motivated. I wanted to do well, stop wasting my potential and get the chance to transfer my credits over to her school so we could be by each other’s side again. At first it wasn’t so bad. We’d talk every night, played WoW together between homework assignments and generally kept each other updated with what was going on in our lives.

All the while, I’d be saving every dime I had to l to get over there to see her. In retrospect it was a poor use of my money, but I loved her and wanted to spend as much time with her as I could. So things were going as well as they could be, for a while. Then one autumn rolled around, and she fell into her depression like she always did at that time of the year.

I did my best to keep her spirits up as I always did, but this year it wasn’t working. She just kept getting quieter and quieter, retreating from me with each passing day. I should have seen the signs then, but I just figured that school was putting pressure on her that was causing her depression to become even worse. I could totally fix it. I always had before.

Her birthday was coming up and there was something I know she really wanted (I don’t even remember exactly what it was) that she had asked for previously. I took up as many hours as I could at work to be able to afford the gift and to be able to go out and spend her birthday with her. One 12 hour train ride later, followed by a 2 and a half hour bus ride and I was there at her city’s bus stop around 8 AM.

But she was nowhere to be found. Odd…she knew I was coming, maybe she had class and couldn’t meet me. Guess I had to walk then. So I’m running on fumes since I hadn’t been able to get any sleep for the last 14 hours, it’s the middle of November and there was already snow on the ground so it’s absolutely freezing, I’m walking up every hill there is in the city to reach her dorm which is of course at the highest point, and I’m lugging around the really heavy gift I had gotten her in my backpack that’s threatening to snap me in two.

I finally reach her room two hours later. I’m sweaty, I’m exhausted, and a little annoyed that she hadn’t responded to my texts, but I’m happy because I’m able to see her again. She looks much less happy. She doesn’t even crack a smile when I show up at her door. She accepts her gift, but won’t let me kiss her. She tells me she doesn’t love me anymore.

She doesn’t want me anymore. So I spent the rest of that weekend alone, trapped in her town knowing almost nobody with nowhere to go until my return train comes back in a few days. She could have done this before I left, dumped me before I paid for the train ticket and traveled a total of 16 hours to get to her. Maybe she wanted to do it in person, sure, but I can only assume she REALLY wanted that present.


Vacation Break Up Stories FactsUnsplash

31. That Is Really Not Nice

I met my first girlfriend when I was 16, and we were together until we were 18 years old. We organized a trip with our mutual friends, and rented a little apartment for three weeks by the sea. We were about 5 guys and two or three girls. Five days before the end of the vacation, she tells me she “Only came here to see if I had to break up with you or not,” and left me.

In those 5 days, she slept with my best friend and they didn’t even try to hide it. It was really bad, because I had to wait for my flight, and I had to live FIVE days in the same house as my ex-girlfriend and my ex-friend.

Vacation Break Up Stories FactsUnsplash

32. Over My Dead Body

We just came back from a trip to France and then I rushed off to a funeral in California right after. I told my family that I haven’t seen in years how much we loved each other and how happy I was with him. I said hopefully we would get married one day. I can't believe what happened next. I come home and find out he had been cheating on me. He faked being happy so he could have a roof over his head.

What a waste of four years. It’s OK. I’m single and It’s pretty nice.

Vacation Break Up Stories FactsUnsplash

33. Orca Island Wasn’t Worth It

At the age of 13-14, I paid 50 dollars to go on a trip to Orca Island with my girlfriend’s youth group. She had one of her friends break up with me for her when we were on the ferry to get there. I couldn’t go home and I was stuck with her in a tiny house for a full week. All the while she’s trying to hook up with another guy from the youth group.

Deadly Animals FactsPixabay

34. Those German Math Tutors Are So Smooth

I started dating a girl during college. I met her when I was a senior in high school and she was a foreign exchange student. Well, she obviously had to go back home to Germany so our relationship kind of ended there but we decided to try the long-distance thing while I was in college. It was going great and I would talk to her everyday. I made plans to fly to Germany to go see her for two weeks.

We were both excited to see each other again and planned on moving our relationship forward. Fast forward. I arrive in Germany and things are going well. On the THIRD day of my TWO WEEK stay at her place. She tells me she doesn’t feel the same way anymore. (She met some guy at a party a month prior to me coming there who helped ‘tutor’ her in math.)

She ignores me and flirts with other guys right in front of me for 11 days. I’m living with her and HER PARENTS. (Who were really nice, and mad at their daughter). Worst trip ever.

Vacation Break Up Stories FactsUnsplash

35. Friends Forever?

I dated a guy for 10 months or so. We traveled overseas and had a great time. Stopped in a town where a good friend of mine lived and spent a few days visiting her. Came back home and continued as usual. Two months later, I get an email from the overseas friend saying she’s coming to visit and will be in town on such and such dates. Me: “Awesome! You can stay here, my guest room is ready. Can’t wait to see you!”

Her: “Actually, I’m staying with [the guy I was involved with.] I thought he told you – we started emailing back and forth after you guys visited here and fell in love.”Me: what the eff? emails the guy Him: “Oh yeah. I’ve been meaning to tell you. We’ve fallen in love and I’ve never felt this way before.”

Vacation Break Up Stories FactsUnsplash

36. Bus Ride To Lonely Town

I traveled 10 hours on a coach to Newcastle (from London), stayed for a week. Got dumped on the 10-hour coach journey home. That was nice. In the month or two that followed, he proceeded to give me false hope by getting “back with me” then repeatedly making excuses as to why we couldn’t work, my favorite being “my mum won’t let me have a girlfriend.”

Fast forward a month, he has a girlfriend. A year later, I’m engaged to possibly the best man in the entire world so I am glad it happened or else I wouldn’t be where I am now.


Vacation Break Up Stories FactsUnsplash

37. A Failed Engagement

My fiancé had an internship in Boston while I was still at home in the Midwest. We texted constantly, called a few times a week, and Skyped a couple of times (once she told me she was so turned on that she stripped down and started doing it dirty on camera). Anyway, I make plans to go see her once she’s been there a month. I’m on the phone with her while I buy a $300 plane ticket to go see her (while being unemployed at the time).

So I travel to an unfamiliar city, navigate the public transportation, finally make it to where she’s staying, and receive the coldest welcome ever. I ask what’s wrong, and she tells me we need to talk. She tells me after two years of dating and six months of being engaged that she feels “trapped” and gives me back my ring. And like that, it’s over.

So now I’m an absolute mess and have to change my flight and get a hotel for the night (an additional $500) and fly home the next day. It was not a good time.

Vacation Break Up Stories FactsPxHere

38. A New York State Of Mind

I went to New York on vacation with my girlfriend of 2 years. I noticed that in the weeks before, she had been getting a little distant and was texting on her phone a lot, she would never leave her phone just laying anywhere like usual, always had it on her. The night before we leave I asked her if anything was wrong, and told her about how her behavior was a little suspicious. She reassured me and said it was just stress from planning the trip. I knew better, but I said screw it and went on our trip anyways.

The first day we are there she hardly talks to me at all, every time I would point something interesting out she would just say “Oh that’s cool” and go right back to texting on her phone. So while we were waiting on a table at the Hard Rock Cafe I happened to get a glance of who she was talking to. Was some guy whose name I didn’t recognize, and the message she sent him went something like “I’ll be home soon baby, don’t worry. I love you”.

At this point she didn’t realize that I could plainly see what she was typing on her phone over her shoulder. She texted this guy back and forth for our entire 30 min wait for a table, and she didn’t say one word to me that whole time. I seriously about lost it right there. I wanted to tell her what was on my mind right there in front of everyone in that restaurant.

But I kept my cool and waited until we got back to hotel that night. We still had 4 more days there, and I personally was not about to let her ruin the trip. We got back and I confronted her about it, she went on to tell me that it was just some guy that she was good friends with in high school, blah blah blah. I told her if that was the case then she needed to stop ignoring me and that she needed to stop texting him on OUR vacation. She turned her phone off right there and left it off for the rest of our trip.

I still wasn’t convinced obviously, so I had planned to talk more about when we got home. We get home, her sister picks us up from the airport in my truck, which I had left at her sister’s house since she dropped us off. First thing I notice is that the full tank of gas that was in my truck when we left is now completely gone and the interior of it was full of trash, so her sister drove my truck around for that week we were gone and trashed the heck out of it.

Finally get to where we were alone and I told her that I knew what she was doing. I knew that she was cheating on me and trying to hide it. She starts crying and tells me “I can’t believe you would accuse me of that, I told you he was just an old friend and that we were catching up.” Little did she know that I had installed a keylogger on my laptop and thus saw every message that she sent this same guy over Facebook.

Most of them were very intimate and it was plainly obvious that she was cheating on me with this guy. I had the proof right there in writing, and she STILL insisted that it was nothing and that I was being ridiculous. At that point, I was so completely dumbfounded about her maintaining innocence even in the face of that proof, so I really had no clue what to say.

While I was still trying to process all this she says “I don’t think I can’t keep dating you, you are too insecure and you don’t trust me anymore.” Duh, I just pieced together that you are cheating on me while we were on vacation in New York. At that point, I literally had nothing more to say to her, so I left. I forgot that had quite a few things in her house still.

So when I called her the next day to get my stuff she wouldn’t answer. After that day she would not answer or return any of my calls or texts. I ended up having to get her mom to go get my stuff for me. It wasn’t but 3 days after all this that she had already changed her status on Facebook to show that she was in a relationship with that other guy.

I will never understand how one person could be this terrible to another person, let alone the person that they dated for two years.

Vacation Break Up Stories FactsUnsplash

39. Full On K-Drama

My girlfriend had cheated on me and I caught her, she cried and begged and I decided not to break up with her. It took me a while to trust her again. We decided to move to Korea together from South Africa and we lived there for two years. One time she went to visit her sister, who was also in Korea, and I had to stay behind and work.

Months later I get home from work and she is on the bed crying saying she can’t lie anymore, she cheated on me while she was visiting her sister, she feels terrible, please forgive her…. I do… We finish working in Korea, she wants to travel Central and South America before moving back to South Africa to study some more. We spend a year backpacking from Northern Mexico to the Southern tip of South America.

We get back to South Africa and I am struggling to find work because there is no work in South Africa, I freelance as an environmental impact assessment contractor and let me tell you the work is not steady. I end up having to go to very remote parts of the country to try to keep making some money in between the periods of no work.

I get back from the middle of nowhere and walk into the door. She says we need to talk, she asks me to leave and go to my parents. I am shattered. I go to my folks, we break up officially about a week later… I spend six months living with my parents in a terrible state of depression. I guest lecture at universities but am drinking a lot and don’t care.

I decide to move back to Korea. Dad and Mum agree that it’s a good idea. I still speak with her a bit. One day she says to me that we shouldn’t be friends on Facebook and we need to take some time not talking to each other. I readily agree. She e-mails me a few months later and says she feels guilty and doesn’t want to lie anymore. She had been dating one of my “best friends” since I walked out the door to go home to my folks.

I say “all I ever wanted was for you to be happy and if it couldn’t be with me I hope you can be with him.” I never spoke with her again.

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40. I Didn’t Realize This Was An Open Relationship…

Living with my fiancé in a different state for school, she is getting ready to go out after I come home from my part-time job. Generally this would be a thing we would do together or at least have a brief by the by “oh hey I’m going out with my girlfriends tonight”… I naively believe I should get ready but as I do I get “oh how bout I get a rain check” on me joining her.

An hour passes at home, I decide to go get a 6-pack at the gas station and some Arby’s (comfort food) to settle my nervous stomach. As it gets later I drop by an acquaintance’s place to try and sort this out. I say “acquaintance” because after a year of living in a different state and not being socially forward the only friend I had was my fiancé.

I leave slightly buzzed, more confused, and headed for the unfamiliar night scene to satisfy my curiosity. 20 miles later, the first random place I arrive at is a busy nightclub on the beach. I order a drink and immediately spot my fiancée across the way. She’s with a guy she works with, I only recognize him from the night she oddly made me go out and have dinner with him and his best friend 3 weeks earlier.

They are clearly on a date. I can’t believe it, I’m in such shock, at the same time trying to remain unrecognized as I work angles, hiding to look through shaking tears at their very intimate moment… perversely interested in seeing where this goes to try to make sense of this blind side. Gut wrenching moments pass, one after another, kissing, hugging, laughing, looks that had only been reserved for me.

I gathered the nerve, I decided if I could walk over, pull her hand, and see the ring I gave her, it would tell me all I wanted to know. That she either lied about being engaged and was not wearing it. Or the guy knew and was a piece of trash for scheming on an otherwise to-be married woman. I walked straight up to her. She was not startled or concerned at all by my intrusion to their date.

I grabbed her hand to look close. She was still wearing the ring. I told her calmly “It's over.” She mouthed “What?” I realized I could barely squeak into her ear a second time over the loudness of the busy club “Its over.” No response. Somehow I made it back to my car shaking and sick to my stomach. It was a 45 minute drive back to the apartment. I called her mom.

I was close with her family and I wanted to let her know that it didn’t work out and that we wouldn’t depend on each other anymore. She didn’t come home that night, and I didn’t sleep. I packed my car to head home 4 states away. She arrived mid-morning with just enough time to muddle through a circular argument about how inadequate I was.

Numb and lost, our puppy and I took an unplanned 10 hour drive to my parents that summer afternoon.

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41. Skype Breakups Are Never Fu

I went for a two-week vacation in my home country last 2014. I had a great time. Met some friends, enjoyed, had a good time in general. Then three days before I’m scheduled to fly back to Dubai for work, my then-girlfriend and me went had a Skype session to catch up. She lived in Dubai as well. She broke up with me on the Skype call and right after dropping the call started posting some photos of her with another dude on her social media accounts.

Photos included gifts from said dude, the works. It then occurred to me that I got cheated on.

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42. Can I Breakup With You But Keep Your Family?

After a few years of dating and just under a year of living together, we were out at Lake Powell for a family reunion/vacation with all of his immediate family (8 siblings, their significant others, and kids) and some extended family, all staying on a houseboat together. He lied about something. He lied about a lot of things and I usually just let it slide because it was usually such a pointless lie that it didn’t matter (ie “I only gamed for 2 hours last night” when it was 6).

This time, he was trying to throw my roommate and longtime friend under the bus and I caught him in the lie.  When we were away from the family, I confronted him about it very calmly and asked to talk to him about why he lies about little things that end up just making his life harder. Well, instead of having a conversation with me in a neutral and private environment, he lost it, went back to the houseboat and started packing all our stuff and yelling to his entire family about how I was psychotic and manipulative and he wouldn’t put himself in such a toxic environment anymore.

Told my 5 year old several times that we had to leave because his mom is crazy. The entire time I was silent, and just let him pack. Pretty soon into it, I took my son away from the situation because it was that dramatic and psychologically harmful. I was silently crying and his sisters and brothers were coming to hug me and tell me they love me (they all know how he is).

He demanded his brother drive us the 1hour back to the marina, 2 days into the 7 day trip. I gave him a ride all the way home (a couple hours) in my car, because his car had been repossessed a few days earlier. Silence the entire way home, and then he moved all of his stuff out while I took my son to the park.

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43. London Falling

We were on vacation together in London…I flew from Florida to see him and we had just spent 3 amazing days in Paris. I was on cloud 9. On my second to last day, he woke up, took a shower, and when he came out he told me “we didn’t have what it takes to make it long distance.” He left me sobbing in the hotel room, hours before anyone at home was even awake to console me.

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44. The Feelings Are Distant

I met a girl a few years back when I lived in London, we spent a few months together before I returned to Australia. The following year she came over and spent 3 months with me before she returned to the UK. We never actually broke up, we just left it as a ‘see you again soon’ kinda thing. The year after that I booked a flight to London to spend a few weeks with her.

The day after I booked my flight she told me she was seeing another guy. It was going well with him so she decided the thing we had was officially over. Now I totally understand the difficulties in staying with someone who lived on the other side of the world, but come on, coulda broken up with me before I booked the bloody flight!

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45. Disney Heartbreak

I was 15. I lived in MA and my dream was to go to Disney World at the time. My boyfriend was going to Florida with his family for a week and his family invited me to go with. It was the most magical time. In my head, everything was going so perfect… I got to go to my dream place with my first love. I fell in love with him so fast and so hard.

His family loved me, my family loved him. It seemed so right! Then the day we got back from this amazing vacation, he broke up with me… Through email! I asked him why and never got a response back, ever. He could’ve at least waited a week after coming back! Way to break a young girl’s heart. But here is a happy ending to this story…Now I’m happily married and live in Orlando.

I can go to Disney World with the hubby anytime I want!!!!

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46. This Guy Sucks

A guy I know had spent months planning a trip with his 2-year girlfriend to the Middle East and Europe. He arrived before her, and apparently started hooking up with local women. Emboldened by his newfound ability to get with the ladies, he decided to break up with her. Here’s the kicker — he WAITED UNTIL SHE LANDED to break up, reasoning that it’s better to do it in person.

They had a multi-week trip planned together, complete with activities and lodging, that she’d already paid for. Needless to say, dude isn’t my friend anymore, for totally different reasons.

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47. No Chemistry Is A Recipe For Disaster

I broke up with someone while we we backpacking in a foreign country. Just the two of us. I did it in the first week of travel of a month long trip. In my defense, I could Not pretend to be romantically interested in this man for a second longer. The thought disgusted me. We had been dating long distance prior to this and I quickly saw a side of him I did not care for shortly into the trip.

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48. This Is Why I Only Love Pizza

Timing is everything! A cousin of mine flew to Italy for a 6 week trip (with his girlfriend who was living there at the time), their plan was to travel and hike all around Europe and finally meet her entire family in Spain for a rather grand festival. He broke up with her as soon as he arrived on the plane…And they then proceeded to go on their trip!

He said that it was rough, and that there was a lot of crying (he seemed very surprised at this). We don’t see eye to eye on many things.

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49. The Most Spiteful Breakup Of All Time

I work for an airline and I heard that this guy I work with found out that his girlfriend was cheating on him. He got the most brutal revenge I can imagine. He told her that he wanted to go on vacation and they flew to Japan. They checked into the hotel, then he waited for her to fall asleep and went back to the airport, canceled her ability to use his discount, and then flew back. Leaving her stranded in Tokyo with no money.

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50. Cleopatra Would Never Have Dumped Me Like This

This was a bad one. I was in a great relationship for three years. We had moved in together and I had just gotten my dream job. I was paying the rent on our apartment, lots of good fun, friends, parties, and life was sweet. I was so in love. Anyway – one day she says she needs to go traveling. To Egypt. She’d been there before, and loved it, plus she’d just lost her job, and she needed to clear her head.

So she wants me to quit my job and go with her. So I did. Walked away from my dream job, and got on the plane with her. We spent 3 months traveling all over Egypt, hated it, too many nasty men trying to hit on her (she’s cute and blonde) and I was ready to kill someone in that heat, so it was time to go home plus we had no money left.

Then she gets a job in a bar, and we’re arguing because this bar is always full of sleazy guys and backpacker hippies looking to get free drinks. And I’m really sick of the heat and dust. I have to go back home, she refuses (even though the deal was if I made it to three months out there & didn’t like it she’d come back home with me). Heartbroken I get the bus to the airport, wave her goodbye, come home and immediately regret it, I miss her.

Anyway, she stays out there another 3 months. We chat on the phone, Skype, whatever, but she’s not coming back. Suddenly I get a call from a friend. What he told me made my blood run cold. He says he saw her in our hometown. So I call her parents, they don’t tell me anything apart from yeah, she’s home but she needs to figure out her head, she’s not well.

I’m worried, but I leave her to find the right time to see me. A week later I hear she’s visiting all our old friends. So I go see them, and they say “oh you just missed her, she was here” and she has no cell phone so I don’t know what’s up. I eventually find out that she got back and started dating a friend of mine. A real dumb guy too, so I’m really upset. Want to kill him.

I realize all my friends have been lying to me. I freaked out. Luckily I got offered a job in another state hundreds of miles away, a real party city too, so I say screw em all and move into my new job. It doesn’t take long to get over her, I’m meeting new people and having more hook-ups than ever before, really enjoying life. I got my confidence and my mojo back.

Then she gets a job in the city next to mine, where she knows nobody, and she’s calling and suddenly she wants me back. By this time I’m dating four women at the same time and just don’t need her drama. She turns up at my place and I have a hot girl in bed, but I invite her in anyway. Hot girl gets dressed and it’s sort of cool but awkward.

Long story short, there was lots of talking and we end up in a threesome. Which was good, but still awkward. Then she goes back to her city, just a few miles away, and so we start dating again but no way I’m exclusively with her. She’s upset about this. I say let’s see what happens, I still have major issues about her hooking up with my friend. We argue a lot and I just don’t trust her, it’s just destructive for both of us.

So eventually I head over to her new place and I see her walking hand in hand with a guy. She sees me, drops this guy’s hand and comes up to give me a hug. Guy is not happy with this, wants to fight, he’s much smaller than me and it’s no big deal. Turns out she’s been seeing him for weeks. At this point, I was done with this girl for good.

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51. You Think That You’re Still Invited?

I went to visit my girlfriend who was on a year abroad in Paris. We wanted to take a couple of weeks to travel around Europe. She gave me a cool reception on arrival and seemed to have business to attend to. I was perplexed but passed some time by taking a walk in Paris. On my walk, I was lucky enough to see her walking hand in hand with some guy. I was so stunned that I just went back to the hotel and when she came back and I asked her what was going on, she proceeded to say she was seeing this guy and was breaking up with me.

The whole trip was arranged, all my money was paying for both of our fares, rental cars, lodging etc. And she still expected to go on the trip.

Vacation Break Up Stories FactsUnsplash

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