People Reveal The Moment They Regretted Breaking Up With Their Ex

Breakups suck. Even when they're the best thing for you and everyone involved is good with it, they're still kind of sad. It's so much worse when you realize the breakup was a huge mistake. One Reddit user asked:

What was your 'oh sh!t' moment when you realized you shouldn't have broke up with your ex S.O.?

The responses were rough, honest, heartbreaking, and eye-opening. The sorts of things that make people realize they were wrong were shocking. Some of the breakup reasons were really petty to begin with, and Facebook factors into more than one story. In all of that, though, lots of lessons were learned. Brace yourself, some of these stories are really sad or infuriating. But it's not all bad. I made sure to give you at least one happy ending.

You're welcome.

Merry Christmas, Mom

My mom left my step dad. She was always traveling back and forth 2 states over to take her grandma to chemo and during that time his father passed away and they just couldn't reconcile. They loved each other but life, you know?

He got remarried to a great lady and is super happy now. My mom told me recently that leaving him was the biggest mistake she made because he was the only good man she ever really knew. We all have Christmas at their house (seriously he and my mom divorced and he's still grandpa to my sisters kids and we call his new wife our step mom. They're awesome) but my poor mom has to watch them being happy together every year while she lives alone.


Mourning Me

It really f*cked me up when I broke up with my fiance ten years ago because I realized I could never be the same person I was with him, with anyone else ever again.

That sounds emo, but we had so much backstory, so much history, so many inside jokes, so much shorthand for everything. We'd known each other for 15 years.

I had to mourn the loss of a part of me, a whole side of my personality, that I would never get to be again. Besides just losing him.

Obviously you can build history and jokes with new people, but it's not the same of 15 years of history from age 16 to age 32. Those are formative years.

Regardless, it was the right thing to do to leave him. Realizing what I had lost made it even harder. But it was the right thing to do for many reasons that aren't for here.

- LauraMcCabeMoon

The Wedding Photos

My friend dumped his girlfriend of 12 years because he'd never dated anyone but her, they were struggling financially, and he wanted the chance to experience more relationships. Right after the breakup, she finished her PhD and started making six figures. She found someone else then got married within a year.

My friend tried dating a couple of people, but none of them have worked out and he still misses her. He said the moment he realized that he made a huge mistake was when he saw her wedding photos on Facebook and started crying.

- sleepytimeghee

Lesson Learned

I left her for someone else because I'm an idiot. The other girl turned out to be a jealous, mentally and physically abusive psychopath who eventually ended up in a psychiatric hospital. My S.O, quite rightly, refused to take me back.

Lesson learned.

- caddy1984

Irrefutable Evidence

An old friend left his wife because he felt the sex was awful and he wanted someone who he felt he could have great sex with. Wife pleaded with him to stay (no kids) but he refused and filed for divorce.

Divorce is finalized about a year later. This guy dates lots of women, but still finds the sex unsatisfactory.

Meanwhile, ex-wife meets this other guy about a year after the divorce and they have that type of whirlwind romance that truly is from a rom com. She marries this new guy, they have kids and the perfect marriage. She tells everyone that the divorce was the best thing that ever happened to her and can't believe how happy she is and could never imagine that a marriage could be so wonderful.

The guy, who is my friend, is more miserable now than ever. Constantly says what a mistake he made leaving his wife. Doesn't even go on dates anymore and has not had sex in years.

That's a rough way to find out you are bad at sex, but believe me he now knows it's HIM who has work to do in that department. The evidence is irrefutable.

- Analytica0

Changing The DJ's Set

I broke up with a woman I was head over heels in love with over something that on reflection was fairly minor. Spent half a year progressively dropping into a deeper and deeper funk. Wouldn't admit it to myself at all that I'd made the wrong choice.

I was hanging out with a friend when she pointed out to me that she had never seen me as happy as I'd been when I was with my SO. Another friend pointed out that same week that the music I'd been DJing had become much more depressing over the past few months and asked me if something was wrong. That woke me up and made me realize how special she had been. It took another year for me to realize she was the first woman I'd really loved in the way you come to love somebody for who they are, rather than what you imagine them to be.

I never saw her again. I wish I'd never left her. We only would have had six years together, as she came down with cancer that eventually killed her. It didn't change how I felt; I'd take those six years in exchange for all the years I have left.

- helldeskmonkey

The Happy Ending

When I saw her at her birthday party with another guy.

It was kind of a mutual-ish breakup; it was my first relationship so I found it kind of oppressive.

Weeks later, I took her to dinner and told her I thought we had a future together and that I would be more committed to the relationship.

We've been married for 11 years now :)

- mercurialchemister


We were on a break cause I was being a dick. In order to get a reaction I ended the relationship on Facebook. That was the end of the friendship and all. Regretted it ever since. It's only added years of misery to my life

- 753951321654987

Overwhelmed And Suffocated

I pushed her away because I got overwhelmed. I don't know if it's an oh sh!t moment, but I miss her.

I have this habit in relationships where I always end things whenever I feel overwhelmed. I really, really loved her. But little things start to pile up. I don't say how I feel because I just don't like confrontation. And then one day I just didn't love her like I used to. I don't know why. And with her, I fell back in love with her for a while and I opened up to her about it. She tried to get me to open up to her more regularly about how I'm feeling, but I just...can't.

I fell out again and ended it. She tried so hard to figure things out with us, but it just...I didn't want to try. It didn't seem fair to her to continue this when I'm just going to keep feeling suffocated. And when she tried to help, I felt trapped.

I don't know why I'm like this. And I know she really cared and loved me. Part of me wants to reach out to her again and really mend things, and figure out how to not feel so suffocated anymore. I don't think it's anything she did, she was really understanding...it's just me. I don't know how to deal with me. And I miss her.

- shieldedroar

The Captions

I checked out his new girlfriend's social media accounts and saw how they were living exactly the same kind of life we had, and also living out things that my ex and I had planned. The difference is she seems so, so happy about it. Her captions about him shows how she treasures him and thinks highly of him, like she's so lucky to have him. He is indeed a good man. But during our time together he hadn't really figured out stuff yet. I felt like I always had to encourage him, to motivate him. I felt that I was always going to be the captain and cheerleader in the relationship.

When I read his current girlfriend's captions, it wasn't an 'oh sh!t' moment exactly, more of a disconcerting feeling of 'Was I wrong? Should I have been happier with that role? With what we had? Should I have not wished for more? Is there even a 'more'?'

But ultimately, I am happy for him. I don't think I'd ever be loved like that again tho.

- likhaanoushka

Missing What's In front Of You

Because I was a very stupid young man who wasn't thinking at all. I had dated her for a little bit before I broke up with her, cause another girl who I thought was hotter showed a lot of interest in me. And it got really messy after that before we simply stopped existing to one another. That girl I left had been my longest steadfast friend who cared about me way more deeply than I ever deserved. Every relationship since then has exposed very deep flaws in me as a person and allowed me to make very fucking stupid mistakes that I wish had never happened. Every so often I think what if, but I'm not dwelling in the past. She now has an amazing man and I wish them the utmost happiness in this life and the next. I have worked tirelessly to reform myself so I never hurt anyone or make the mistakes I did, and also so that if I meet a girl like that again, I don't mess up again.


"I Don't Blame Her" 

One of my Ex's I just never made time for. She was a great girl, we got along well, I just had different priorities at that point in my life.

She brought it up to me twice, she put in effort to fix it, tried scheduling dates, sat down and talked to me and explained why she was feeling hurt. And I'd change for a week. But I'd go back to my old ways. I just wasn't committed. I had other focuses namely my career. Finally she just said she still enjoyed my company but couldn't call seeing me once a week for a 2-3 hours a relationship. Even after she tried to stay friends but time between my responses got longer and longer until eventually I looked at it and her last text was from over a month ago. I felt too ashamed to respond, I probably should have.

But I don't blame her. She had needs I was not paying attention to. So I guess it's more she broke up with me, but she didn't want to. I forced her hand by just not being around.

The important thing was I learned from it. I learned I needed to pay more attention to my partners. I learned that just because I am very long-term focused that I cannot ignore the more immediate concerns and justify it with "It'll pay off in the long run". And that is a lesson that has lead to success since then.


Butt What?

Not me, but a friend of mine dumped his girlfriend of 5 years because he'd never gotten to have anal sex, and wanted to try it, and his girlfriend wouldn't do it because she was in remission from her fibromyalgia and she was afraid that the pain would cause a relapse. His girlfriend came from a wealthy family, and was supporting him financially at the time but apparently anal was just that important to him.

He dumped her and realized almost a year later when he finally met a girl who was willing to let him do anal that he was completely repulsed by the reality of it. He had been in denial that he'd made a mistake before then, but really broke down after he finally did the act. He was broke, and basically homeless (couch surfing). He missed his original gf, she'd been the only woman who'd had the patience to handle his eccentric personality for more than a couple months. He tried to get back with her but she'd moved on. He's never fully recovered in my opinion, he's still essentially homeless and has developed an alcohol problem in recent years.


Should Have Listened

One of the last things she ever told me was "you're going to be single for a long time." It's been 2.5 years. She was right. Not that I necessarily want to be with her again, but she was right that it would be hard to find someone again who'll give me a chance.



When I was 16 I briefly dated a girl who was 17. She wasn't in my peer group; she was an "outsider". But she was nice, had curly blond hair. I liked her. She had an old 1970 Cadillac and she let me drive it. I had never driven before so maneuvering that giant boat on the narrow streets of town was...fun. After a few months my friends were bugging me about why I was wasting my time with this girl. She didn't smoke or drink or listen to hard rock. So I let us drift apart. She turned 18, graduated high school and then won the New Jersey state lottery for $6M. I should have stayed with her. My friends were all bums.


With Friends Like These...

The break up was kinda mutual (didn't want to break up with him but, I had no choice.) A few weeks after we broke up, I started to catch up with some friends - all of which tried to take advantage me. The first guy wanted nude pictures of me, the other tried to get me into bed. I felt very sh!tty and disgusted, and couldn't help but remember how gentle and careful my ex was with me.

- mediocrityismyforte

A Mile Down The Road

I hope she sees this.

When I got about a mile down the road after packing all of my things, I truly regretted leaving. We tried to hang on for a month afterwards but it didn't take. She couldn't handle that I just left instead of staying and trying to work on things. It's my biggest regret.

I was too wrapped up in myself to really see what was causing all of our issues, I only wish I could've seen it sooner. I tried to talk to her about it, to show her that I know now what I could do to help mend everything but I caused too much damage and pain.

I hope to see her again one day, but all I can do now is work on becoming the best person I can be. I'm currently working on all of my issues that caused all of these problems. It just saddens me because I know that down the road I'll meet someone new who will have this version of me that I will have put a lot of time and effort into. But in my mind's eye my ex is the one who deserves all of that work from me.

- WhiskeyWallace

Mean What You Say

I wasn't the one the broke up with my ex, but breaking up was always a topic that was there due to long distance. We were talking about the future one day and she was pretty adamant about pursuing her career, which meant she wasn't planning on moving back with me. It turned sour really quick and I threw out a "maybe we should start thinking about breaking up."

The next time I visited her, she told me that she decided - and we broke up. I guess the "oh sh!t moment" didn't hit me until a month after when I tried to win her back by flying out to her (I had to give her stuff back, at least that was my excuse). But it didn't work and might have been even more painful cause it seemed like she had someone else already.

When I got home I sat on a bench in a park and couldn't stop crying. I felt like what I just lost was equivalent to losing my best friends that always followed along with all the dumb childish ideas I had, losing my mom with her undying love and loyalty, losing all the vibrant colors that are in the world that made everything seems so beautiful, losing my dreams of possibly one day having kids (I never really liked kids but I always thought if we had kids they would've been awesome), and then some.

The "oh sh!t moment" lasted for about a year, and I still remember her fondly with no resentment because I was dumb. But I take the advice "say what you mean, and mean what you say" pretty seriously now.

- kevwjj

Mental Health Crisis

I left my girlfriend at the bottom of a debilitating mental health crisis. I guess I just ran out of energy for it and figured if I was good enough to get her, I was good enough to find someone easier and healthier to be with.

Nope. Coming up on five years. She recovered completely, no other woman has shown a shred of interest since then. All I had to do was stick it out.

- iron-while-wearing

H/T: Reddit

I'm not exactly prone to winning things - but I do have one glorious moment of winnerhood that really is all I need in life. As a child, my church would throw Halloween parties every year. One year, I was handed a raffle ticket along with my trick-or-treat candy. At the end of the night, ticket numbers were called - mine was the last one called. I still didn't know what the prize was. Once I made it up to the stage to collect it, I was presented with a box of puppies and prompty LOST MY TEN YEAR OLD MIND. I thought I was just going to cuddle them, but nope! I got to pick out my brother and I's best friend for the next decade. We named out litlte box puppy Bear not knowing he would grow up to be a massive doberman who weighed triple digits.

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Listen to me, if you never take another piece of advice in your life, take this one: take any advice anyone gives you with a grain of salt. Yes, I'm fully aware of the irony happening in this article right now.

I've been on the receiving end of TERRIBLE advice. Example: I was explaining to an acquaintance how frustrating it can sometimes feel to be so short - not just because I can't reach things or because of my spinal pain, but because people often treat me like a child. They unintentionally treat me like I'm dumb, naive or otherwise incapable. That's when this person hatched their master criminal plot for my life.

I should just go ahead and park in handicapped spots and ignore any tickets I got for it. According to them, since I have occasional spinal problems I should probably have a tag anyway. I could just ignore tickets until I had to go to court, then show up in court and play naive and nobody would ever really punish me for it. Dude. No.

One Reddit user asked:

What's the worst piece of advice you've received?

Believe it or not, it gets worse. Here are some responses:

No Mom, No. 


My mom told me that if I like a girl I should just follow her everywhere she went and give her gifts, like a vial of my blood (actually said that).

No mom. No.

- huazzy


"Never go to bed angry."

This was written in lots of wedding cards! We totally ignored this advice. Because if you're tired and getting more cranky you're more likely say something you will regret. We just sleep on it and in the morning, if its still worth discussing, you can go in with a clear head - or sometimes its not worth bringing up and you can both move on with your day.

- _northernlights

Never Trust The Roommate

Dating a girl in Uni, her roommate told me she "loves an*l, but is shy about saying it."

I learned:

A) Always discuss an*l in advance

B) Never trust the roommate

- billbapapa

No Effort Needed

To not put any effort into finding a partner. Just sit back and it will happen.

That might have worked once when people were more social and went to church regularly and things like that. Also it was common in the past for older people to make an effort to introduce single people to each other. Society just isn't like that anymore.

When I was single, my way of life put me into contact with very few people who were actually single and eligible and interested in me in return. If I hadn't put the effort in to meet someone I would have remained single.

- Waitingforadragon

Your Parents Don't Know Everything

My parents encouraged me to go to a University that costs $63,000 with no financial aid when I had no idea what I wanted to do with my life. "You'll figure it out" they said. They also had me deny the federal student loans I was granted through FAFSA as it wasn't worth it.

I transferred, graduate in May, and that 1 year in school is 45% of my 4 year aggregate debt. Declared a Finance major so I can make informed decisions and not rely on their shitty advice. I'm trying to get into one of the best Macc programs in the country and that debt level is seriously inhibiting my ability to go if I get in.

Your parents don't know everything.

- kingbrownied1

Change Him

"Marrying him will make him change."

Followed by...

"Having a kid with him will make him change."

Followed by.....

"Having a second kid with him will make him change."

Followed by....

divorce papers and child support.

- ghost0427

Because Other Men...


I was once taking my buddy's girlfriend for a walk because he asked me to keep her busy while he was at work. While we were walking, I stumbled upon an old high school classmate of mine who gave me that look of "damn, what you got there?"

I didn't pay any attention to it and just kept walking. After a while he sends me a message on my phone, asking me if that's my girlfriend. I told him she wasn't, I told him she was only my buddy's girlfriend who I was keeping busy. He told me to "steal" the girl and I obviously told him that's ridiculous and that I would never do something that disgusting.

His advice to me was: "Just do it because other men will always do it to you." The most ridiculous piece of advice I have ever had the displeasure of hearing.

- SirOberon

Just Do It Fast

I was learning to drive and kept nosing out to turn but couldn't see if a car was coming (I am turning they would be going straight). My friend that was teaching me simply said, 'Just do it fast'.

- Bodymindisoneword

Not Allowed

Both the worst and best advice... I'd just finished my first day of work for a company who'd hired me to work as a DB admin. Instead of doing anything related to the job title, they had me doing data entry all day in excel. I was alright with it, believing that it was just a temporary introduction type thing. Certainly wasn't what I wanted to do.

Brother asked, "So how was your first day?", "Eh, kind of lame. Data entry in excel is boring and I don't get anything out of it."

To which he responded, "Word of advice, you're not allowed to not like any part of your job. You can like some things more, but never dislike something."

I quit the next morning after having a complete nervous breakdown resulting from thoughts like:

"Is this what working is? What's the point of even existing if I'm not allowed to dislike (and subsequently try to avoid) jobs? Why would I ever want to go through life doing what I hate and trying to smile about it like it's alright?"

I certainly reacted more poorly to that experience than I had to any before in my life, but it made me realize that I would rather be homeless or dead than live working a job I hate for someone I've never even met in a company that doesn't care about me.

I work for myself now, and sure there are still things I have to do for my own business that I may not like... and I may not be all that successful, but everything I do now is for me. I love what I do and wouldn't trade it for any amount of financial security.

- cascade_olympus

Break Up Because You're Happy

Some of my high school friends told me to break up with my boyfriend because we didn't fight. Apparently that meant there was no passion in our relationship. We didn't fight because we discussed problems in a rational manner, rather than screaming at each other in public displays (which were common among this group of friends).

Fifteen years later, I'm happily married to said boyfriend, and haven't talked to those 'passionate' friends since high school ended.


So what's the worst piece of advice you've ever gotten? Tell us your stories.

H/T: Reddit

I object! Where is the open bar?!

There are a few requirements that are a must at every wedding, or at least they should be a must! It's a no brainer... a couple in love, music and a cake. Seems simple enough! It's suppose to be a celebration, not a prelude to a funeral. If your guests are having to put the wedding together for you during the ceremony, or fainting from starvation, or bored out of their skulls because you've allowed family and friends to relish in their fifteen minutes of fame threw self-indulgent speeches... YOU HAVE FAILED!

Redditor u/RedxSmoke was wondering what almost brought them to an "I Object" reaction by asking... What is the worst wedding you've ever been to? What made it bad? Now toss the bouquet!

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We should know our worth when we are working. This goes for anyplace: school, our jobs, our home life. And we know when we can stare somebody in the face when they're challenging our worth.

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They say revenge is a dish best served cold, and I guess that's true for major stuff. Like if someone assasinates your lord, leaving you and 46 of your homies as ronin samurai and then dude takes your girl, too then OBVIOUSLY you devote yourself entirely to plotting and exacting your revenge. Don't even get me started on the merciless vengeance that you can expect if you mess with John Wick's dog. If Hollywood has taught us anything, it's not to anger Keanu Reeves. He's just out here trying to live his life in peace, so he may seem like an easy target, but he WILL end you without even breaking a sweat. There's no sweat in revenge this cold.

But what about the minor annoyances life has to offer? Do they really deserve cold revenge? What about petty lukewarm revenge? Can it be just as delicious? Short answer: YUP. One Twitter user asked:

What is your most memorable story of petty revenge?

Honestly, these don't need a major introduction. It's a parade of pettiness that made several people cackle wickedly. James, whoever you are and wherever your doughnut fingers may be right now, we hope you're happy with yourself, sir. Yours was perhaps the deepest betrayal.

Concrete Pumpkin

I have a friend whose pumpkin\fall display at the end of his driveway would be run over by the neighborhood jerk. It happened every year. Friend decided to put a stop to it.

He withdrew money from his savings account so he would have enough to buy the largest pumpkin he could find, along with several large bags of Quikcrete. filled that puppy up and made a real pretty display.

The jackass broke the axle of his sh*tty car when he hit that pumpkin and could not drive away. My friend had his car towed away, too.

- cuddlenazifckmonstr


My coworker throws out her lunch in the garbage can at my desk instead of her own, because she claims she can't stand the smell of old ketchup that's been sitting out for a couple hours. I've asked her several times to stop, but she will then just wait until I get up to go to the bathroom and do it, and hide my garbage can under my desk so she thinks I won't see it. There's no reason for it. The cafeteria offers lids for the ketchup cups, so she could just put the lid on it and throw it away - but she refuses to get lids and insists on leaving her food garbage to stink up my area.

Now, when she does it, I wait until she goes to the bathroom, take out the little plastic container that she had ketchup in, and put it way in the back of her bottom desk drawer. There's 6 in there now, the oldest is over a month old. So far, she hasn't noticed the smell. Gonna keep doing it and see how long it takes her to notice.

- Brunurb1

Ring The Alarm


In response to an (admittedly pretty good) practical joke, I hid seven battery powered alarm clocks in the perpetrators room. Set them to go off one by one roughly every 40 minutes between 2 and 6 AM. Last one was hid in the ceiling.

- pancakesareyummy

Pay The IT Guy

Someone owed me $50 and refused to pay, so being in IT I reduced their Mailbox size so they could only hold around 10 e-mails, removed them from distro groups so they missed important group e-mails, and every day for like 3 months I went to their account and checked the little box "Must change password at next login"(We used an elaborate pw scheme).

- roguemerc96

The Austin Powers 20-Point Turn

There's a new truck in my apartment's parking lot. Whoever owns it always parks it taking up multiple spots, ALWAYS. Weird angles, close to the stairs, all over the place (no assigned parking unfortunately). Months of this.

I drive a much smaller car than that, and I'm petty/passive aggressive, I've been waiting for my chance. A few days ago was my shot.

I got home quite late and there were zero spots open in my lot. Big truck is parked across 2 spaces again, but there's juuust enough room on their driver side for me to sneak in there with my little clown car. I carefully pull in, making sure not to touch anything, no damage, no nothing. My passenger side mirror is half and inch from their driver side door. I giggled to myself all the way back to my apartment and set an alarm and waited. The following morning I wake up before the alarm to loud door slamming and stomping around. I check out my window and I see the double parking culprit walking around both vehicles, taking pictures, texting someone, taking more pictures, I'm shaking with glee. They then swallow their pride, let out a visual sigh, and climb in the passenger side, clamber over the center console, and Austin Powers 20 point turn their butts out of the spot.

I've never been so proud of myself and my sh!tty, petty, passive aggressive ways.

- Here2Lol

No Labels

My brother did something to his annoy his then-girlfriend. So she took the labels off all his canned food/tins in the cupboards. Are you opening a tin of beans? Or a tin of tomato sauce? Or cat food?

Kinda hilarious.

- WhoriaEstafan

Don't Mess With My Dogs

I found out my then boyfriend was cheating on me. And he threw my dog across the room when we were discussing what he had done. I moved out immediately. More for hurting my dog than anything. So as I was moving out I took his entire porn collection and microwaved them one by one. It only takes 3 second each. Took me about an hour to go thru them all. I put them back in the case, then back where they belonged. Not sure if the microwave was still usable, did not really care. He was also a manager at a restaurant and would bring home tons of food. They had really nice coolers that the food came in so I called the GM and explained I had moved out and that I wanted to return the boxes. He lost his job. Then I was getting collection calls for him, so I gave them the new girls work and personal number so they could find him. He's her problem now.

Don't mess with my dogs.

- Phoneprincess

James Has Doughnut Fingers


Back in the late 90s I worked at Best Buy and one Saturday a month we had to come in 3 hours before the store opened (so 7am) for a mandatory all store meeting where we watch the video from corporate, give out employee of the month awards, go over department goals, and the like.

Well, there was a guy in our department James who was a pretty crappy worker and showed up to the meeting an hour late and the manager took him aside and fired him. Apparently the manager didn't watch him on his way out of the store and he went into the break room and stuck his finger in every single doughnut they brought in for our break. So literally the only mild positive of getting up at 6 on Saturday was ruined.

20 years later and I still miss that doughnut.

- profJesusfish

Brake Check

My friend in high school was such a drama queen but it worked out hilariously sometimes. He was cut off by a driver who had no brake lights and it pissed him off so badly that he followed until a cop was behind, merged around the guy and then brake checked him so the cop would see that he had no brake lights. The holler he let out when the cop pulled the other guy over is still one of the funniest moments of my life.

- ohheyitsshanaj


When my wife and brother in law were younger, she got the best petty revenge on him for something they don't even remember. My brother in law did something to irritate my wife back when they were in high school.

My wife turned off the TV, wrote "broken" on a piece of paper taped to the TV, shut off the power strip, and flipped the batteries around in the remote. Took my brother in law several days to figure it out.

- SteevyT

H/T: Reddit