Most people can appreciate the value of a steady routine in their lives—but what happens when that routine gets broken? For some of us, there are rare moments every now and then when we choose to ignore all our normal decision-making methods and just say “screw it!” before taking some kind of action that we will never forget.
For better or for worse, here are 42 stories about what some of those moments have looked like.
1. It’s a Small World After All
My biggest throwing caution to the wind moment was skipping several days during a work conference to go to Disney World and Universal Studios. No way in heck was I getting a free pass to Florida and not going to the Wizarding World of Harry Potter. When I walked by the castle, I immediately knew I had made the right choice. It was worth every second.
2. I Spy with My Little Eye
A few days ago, I had the opportunity to get laser eye surgery. Without even thinking twice about it, I called in sick to work. This upset my boss, but who cares! It’s only four days later and I’m already seeing 20/20!!
3. A Royal Sendoff
My biggest throwing caution to the wind moment was finally hitting the “send” button on an email I wrote to my husband’s mistress.
4. On the Road to Recovery
When I called my wife and finally admitted to her that I had a drinking problem. That was one hard phone call to make, I tell you what. Of course, she already knew, as most did, but getting it out there verbally was hard. It’s been a year and a half since I made that call. I’ve been both sober and well-hydrated with carbonated water for the entire time.
5. Taking One for the Team
When my friend was being picked on by a bully last week, I went in to fight the guy on his behalf. My friend is fine now, but I have a black eye. No regrets.
6. They Call It “Puppy Love”
I went into a Petsmart store one day and they had a rescue dog there. They were trying to gain visibility for the adoptable puppies that they had available. I had originally come in just to get fish food for the class pet at the school where I teach. I went over to take a look at the puppies, because they’re puppies. Holding one, I thought “I wish I could have this puppy.” Then, I suddenly remembered, “I AM AN ADULT AND I OWN MY OWN HOUSE! I CAN GET A PUPPY IF I WANT TO!!!”
So, I got her on the spot. Left for fish food, returned with a puppy. I named her Lily, and she is all grown up now!
7. Gave It Your Best Shot
Asking my crush out to a dance in middle school in front of all her friends, and a lot of other kids too. She politely declined, but it was a victory for a shy kid like me to even do it.
8. I Believe I Can’t Fly
My caution to the wind moment was my first time skydiving. The plane that they take you up in is such a piece of junk that I actually felt safer jumping out of it than landing in it. Horrible experience, but still proud of myself for doing it.
9. A Feline Friend
The most spontaneous thing that I’ve ever done was adopting a cat on a whim. I’m so glad that I did though, because she’s my bestest buddy in the world now!
10. She Loves Me, She Loves Me Not
I wasn’t sure if this one girl had been chasing me. For months, she had been giving me mixed signals. Then, one weekend, she needed to do something in my city and wanted to stay the night at my place. I said sure, but told her that I didn’t have more than one bed. To avoid being creepy, I first offered to sleep on the couch. She hesitated. I then offered to stay in the bed with her, and she nodded in agreement.
Cue two hours of lying nervously on my side, trying not to come off as a predator while also trying to make awkward smalltalk. Eventually, I realized that we had been cuddling for like an hour and had progressively been getting friendlier and touchier with one another. I finally threw caution to the wind and figured that I might as well just go for it. I lifted her chin slowly and then kissed her, giving her plenty of time to recoil and pull away or stop me if she was not interested.
She did none of the above. We’ve now been together for a bit over six months, and she has made my life so much better. My only goal is to make her happy from now on.
11. No Strings Attached
When I was a little kid, I really wanted to learn how to play a musical instrument. Finally, one day, I just decided to pick up a violin and see what happened. I’ve been playing for almost ten years now, and it has gotten me a full scholarship to the University of Central Florida!
12. All Good Things Must Come to an End
My caution to the wind moment took place just last night. My elderly dog, Brighid, has been going downhill for months. We had been hanging on for a while and truth be told, probably too long. Last night, we came home from a quick trip to the grocery store and she was laying on the ground, barely breathing. She started to seize, and I knew then that it was time to act.
I held her in my arms while the emergency vet put her down. I’ve never cried so hard in my life, but I know it was for the best.
13. We’ve All Been in the Same Boat
When I bought a sailboat. I then quit a decent paying job that I hated. I sailed from New York to the Caribbean, where I hung out for a year before selling the boat back to someone in Florida and then spending the next five months hiking the Appalachian trail. I eventually went back to work for a year, and now I’m currently backpacking through South East Asia for the next 6 months.
14. Cry Me an Ocean
A friend in Australia once sent me some info online about flights that were listed for only $400 as part of a huge sale. My friend casually said “Come visit!” I sent her back my ticket confirmation. She went, “Woah, really??” and I said “If this was a game of chicken, you just lost.” I didn’t even have a passport at the time. I had to scramble to get one, which was a whole thing.
But I’m glad I did!
15. You Just Made it to the Big Leagues
My roommate from college worked with this beautiful woman. When I say beautiful, what I mean is “way out of my league.” At the time, she was dating this good looking idiot who cared more about his hair than he did about her. I went by the store where they worked on Valentine’s Day and discovered that she was upset for a heartbreaking reason.
The idiot didn’t even call her on, in her own words, “the most romantic day of the year.” So, I threw all caution to the wind, said “Screw it,” and went down to the local florist to buy her a bouquet of a dozen red roses. I brought them to her and told her that she deserved better than what she had. Two weeks ago, we celebrated 28 years of marriage.
16. It’s Now or Never
My caution to the wind moment was when I proposed to my wife. I was just at home showering like any other day, when I suddenly started thinking about how much I love her. I decided to just say screw it, I’m marrying this lady. I got dressed and immediately drove straight to her place to propose. No ring, no fancy speech or atmosphere planned. Thank God she said yes.
Six years later, we are now happily married with two kids.
17. Far Away Places
One time, there was a girl I really liked who was moving away to another country. On the day she was about to leave, I decided to just throw caution to the wind and follow her to the new country. We have now been happily married for more than fifteen years.
18. The Wild, Wild West
In the spring of 2017, I met an Australian woman on a dating app. She said she would be in Texas in two weeks and wanted to hang out. Two weeks later, we hit it off super well. We talked a lot about her travels. She had been backpacking around South America but hadn’t really planned the next part of her trip. She just needed to be in San Francisco in two weeks to fly home.
She wanted to do a road trip from Texas to California, but didn’t realize how expensive it would be. Weirdly, I had been saving up for that exact same road trip. When I told her, she couldn’t believe it. But come date two, we discussed our hypothetical road trip…and it became real. The 5 day trip turned into 8 days.
We had so much fun that we didn’t want to say goodbye. After she flew home, we kept in touch almost daily for nearly a year. We still chat on occasion to check in with each other, and I have plans of getting an Australian road trip out of her one day.
19. A Job Well Done
My caution to the wind moment was when I abruptly quit my job at the end of October. I wanted to ride it out and give in my proper notice. But after a while, I decided that I just couldn’t take one more person younger than me talking smack about me behind my back, or one more project being taken from me at the last second. I walked away at lunch time one day and never came back.
20. A New Beginning
My caution to the wind moment was definitely moving out and never looking back. I was lucky enough to have family in Florida who were able to help me out, and enough money in my pocket to get there. I consider myself a successful person now. I can only imagine what would have happened had I stayed in the toxic and controlling environment that I was raised in.
21. Facing the Music
I had been learning to play the guitar for about six months before the end of high school. When it was finally time to leave for college, I had to leave my instrument behind. When I got to college, I would walk by a music store every day and wish that I hadn’t had to give up playing. After half a semester of walking by the store, without thinking about it or planning for it, I actually went in one day and walked out with a brand new instrument.
I’ve been having loads of fun playing it ever since.
22. Highways and Byways
I was living in Kentucky, in a former frat house with some friends. One of my housemates came down to my room one day and said, “Hey, want to drive to Chicago?” To make an extremely long story short, I drove to Chicago to pick up a guy at O’Hare Airport in the wee hours of the morning, but he never showed up. I then drove to Iowa to meet another couple of people, and ended up becoming part of a traveling mascot act at a minor league baseball game for a day. I almost got heatstroke.
Would I do it all over again if I had the opportunity? You betcha!
23. Home Is Where the Heart Is
I was sitting in my terrible apartment, listening to the upstairs neighbor play fetch with his dog in his living room after waking me up at 4:30 in the morning. I had been searching for a new apartment, but all I could picture was my next bad rental. I ended up browsing house listings on the internet, and I eventually stumbled upon a nice townhouse in one of my favorite neighborhoods, in my price range, with all the features that I wanted.
I stared at the listing for a week, then finally said “Screw it, I was going to end up buying a house in a few years anyway. Might as well just do it now!” Things got kind of chaotic for a few months, getting funds sorted out and inspections and packing and moving. Nevertheless, I moved in over a year ago and absolutely love the house.
24. Dating Is an Art Form
When my girlfriend (now wife) and I were in our first week of being together, I had gotten two days off of work. So, I spontaneously told her to pack an overnight bag and then took her on a surprise trip to St. Pete, Florida. We got a room, had a few drinks, and then went to the Salvadore Dali Museum. It was a blast.
25. But What Happened to the Missing Roommate?
My caution to the wind moment was asking a girl if I could call her back the next night after she had called trying to locate a missing roommate who had disappeared. We had talked for a couple of hours that night about the situation. When I finally got up the courage to ask, she said yes, I called her back the next night. Just two months later, she became my wife. We have been together for over 17 years now.
26. Jim and Pam IRL
I had built a life with someone for over four years. We had a very long history together and we were engaged, but he treated me like garbage. My feelings and needs always came second when we were together. So, over time, I got really depressed and eventually started confiding in a guy who I met at work. He was really sweet and we had a lot in common.
After some time, he finally told me that he would back off of being friends with me because he really wanted to date me but didn’t want to make me feel worse with the situation that I was already in. This guy was everything that I had wanted the current guy to be, and I really admired his honesty and everything. I didn’t know what to do, until it hit me. I decided to just say screw it. I left my ex for this new guy.
I knew it would be a difficult thing to do, but I believed that it would ultimately make me happier. I was right. It has been the happiest year of my life. It’s so nice to be with someone thoughtful and respectful who actually cares about me. I love him more than I even knew I could. Trust the gut feeling, people! Just do it!
27. I Wanna Hold Your Hand
My caution to the wind moment was holding my boyfriend’s hand for the first time. I know it’s super lame sounding compared to the skydiving and jumping out of helicopters stuff, but it was a pretty big deal for me. He had his hand right over mine and I knew that he wanted me to hold it, so I did. It was huge for me because I was so anxious about it. I decided that I would just go for it and hold his hand even though we had only been talking for a few days at that point.
Now, we’ve been together for over five years.
28. Journey of Self-Discovery
I spontaneously decided to go on a solo backpacking trip when I was just 18 years old. I’m a worrier by nature and not very good at handling stressful situations. At the time, I was also super introverted. That trip really helped me realize that I am capable of a lot more than I thought.
29. Taking a Year Off
Two years ago, I had a “screw it” year, where I spent less time worrying about consequences and people’s opinions and just did whatever I wanted. During that year, I bought my first house. Now, I have flatmates who pay off most of my mortgage, and I met some really cool people during that time too. I also got my first tattoo. It was of a symbol that is very meaningful to me. I am still regularly getting compliments on it and I still love it myself for having gotten it.
I also tried stand-up comedy for the first time during that year. I’m still doing it regularly. It has allowed me to make some great friends, and it’s been amazing at helping with my depression and social anxiety.
30. A Change of Plans
My wife and I first met before high school began, at a summer school head start program. Ten years later, we were still good friends but we had both always dated other people. At one point, she was in a bad relationship and I had just left a crazy one. She left him. Her lease was up in a month and I had just bought a house. I told her that we could be roommates and that she could pay half my mortgage. The house had two bedrooms.
We… uh… never got her bed set up…
We have now been married for 7 years, and we have two beautiful daughters.
A few years ago, I met a guy on PlentyOfFish (yeah I know, make fun of me later). We were talking for about a month before he finally asked me out on a little lunch date. We went on the date and had a great time. Afterward, he asked me if I wanted to go back up to his place. Mind you, I was raised very conservatively and also to be essentially scared like crazy of guys.
My mom had always taught me that guys just want to take girls to their places so that they can take advantage of them. Against all of my better judgment, I agreed and we walked back over to his place. We had a good time and just watched a little bit of TV. After a couple of hours, he walked me back to the diner, I gave him a kiss on the cheek, and we parted ways. We just got married on August 31st of this year!
32. I’d Call This One a Fumble
My caution to the wind moment was when I joined my high school football team completely out of spite for one of my classmates. I don’t actually know anything about football, and so far I absolutely hate the experience.
33. Getting Better Every Day
My caution to the wind moment was when I decided to try an illegal substance for the first time. I didn’t actively seek it out. I was just in the wrong place at the wrong time, and with the wrong people. At first it felt good, but then it all fell apart. It felt incredibly euphoric, almost too euphoric in a way. I started doing it more and more after that, and this led me down a ten-year spiral into a debilitating struggle with addiction.
I have been clean for three years now though, so there’s that.
34. Two For the Price of Many
One night, I was sitting at home alone in my crummy little apartment when I decided, for no reason whatsoever, to go to the nicest steakhouse in the area and order the most expensive thing on the menu. It was a giant steak that came with two lobsters. I didn’t care about the money or anything. I just threw all caution to the wind, did it, and I still have no idea why.
It all worked out really well, though, because not only was the food simply magnifique, but the waitress was a very cute lil lady. The two of us got to chatting since I was alone and it was later in the night. Then, all of a sudden, I spontaneously just asked her out on a date for that night after she was done serving me my big fat steak. She said sure, because maybe she figured I was rich or something.
Now, it’s eight years later and wouldn’t ya know…she never went on a second date with me! I wonder how she’s doing these days. Or what her name is, for that matter…
35. Adopting a New Policy
My caution to the wind moment was when I became a foster parent. I had to fight the system tooth and nail to be able to adopt our placement child, even though she had been with us for a year and a half. Even so, things worked out so amazingly well. This was one of the best and most challenging things that my wife and I have ever done. No regrets.
36. A Birthday They’ll Never Forget
A few years ago, I was asked by a rather open-minded friend if I could assist her in planning her dream birthday party. I should specify at this juncture that her dream birthday party was, essentially, a group of adults sleeping together. Being the kind, organized friend that I am, I told her that I would be happy to help her out. And so, I spent the better part of the next two weeks organizing and planning the event.
Now, for those of you who have never planned this sort of a party, allow me to inform you that it can get very complicated in less than traditional ways. Nevertheless, I did it for my friend even though I was raised conservatively and my comfort level with anything like that was less than stellar. Finally, the big day arrived and there I was, clipboard in hand and a fishbowl full of lewd equipment in my lap. The guests arrived and the party soon started.
At the stroke of 8:30 in the evening, my friend gloriously descended the stairs in a feathered, Hollywood-style movie star robe and then abruptly dropped it, revealing her full-back tyrannosaurus rex tattoo. That was when I had my very definitive moment of “Well, my friend is naked on the stairs, there are 15 dudes and ladies in the room with us, and this might be one of the weirdest nights of my entire life, but screw it. Here I am and I’m doing it.”
If that’s not throwing caution to the wind, I really don’t know what is! At some point, I looked around over the sea of pasty white middle-aged weirdos and realized that maybe being a well-rounded adult is deciding that you want to have a party of this kind for your birthday and that there’s nothing really wrong with that as long as everyone consents. It was, weirdly, one of the most wholesome and affirming nights of my entire life.
37. Nothing Is Ever One Hundred Percent
I once threw my caution to the wind and told a woman how I felt about her, despite being 100% confident that she didn’t feel the same way about me. We have now been married for about two and a half years, and we have a beautiful baby girl. Follow your dreams, gentlemen. You never know, apparently!
38. Getting Nutty
I was once faced with a choice between eating all the peanut butter cups at once, or behaving like a normal civilized person. I threw caution to the wind. I ate all the peanut butter cups.
39. Taking the Plunge
I was just a photographer. I photographed lots of guys going out the back of aircraft over the years, but had never jumped or roped myself out. One day, I was shooting some folks during a week-long training exercise, and they asked if I wanted to make a go of it. No pressure. The guy in charge even told me that the aircraft could easily just land if I didn’t feel comfortable. But, I figured that if other people can do it, then so can I.
So, I got a few days of training on the tower, and then it was off for the flight. I was as nervous as could be, even though they told me it was probably just going to be a twenty-foot drop. As we got closer, we started counting down the minutes. At two minutes out, the door was opened up. At thirty seconds, we unhooked and sat on the floor. It was nighttime out and I couldn’t see anything. I was hyped up with nerves and energy, but I was positive that I wanted to prove to myself that I could do it.
“Remember,” the person behind me said, “if you get hurt on the way down, roll to the side as quickly as you can, otherwise I’m landing on you and that’ll just suck.” And that was it. The person in front of me was out the door, and the crew chief was slapping me on the back. My feet went over the edge, and the only thing that I remember thinking is “Screw it!”
It was pitch black, but I remember thinking that it felt like a much longer drop than the tower. I hugged the rope close to my chest and kept my feet kicked out like they had told me to. Eventually, I saw the bottom and landed more or less upright and in one piece. I even managed to get clear in a few seconds, and get some good video of the next person dropping.
Later, I found out that what was supposed to be a twenty-foot drop had somehow turned into a fifty-plus foot drop. In the dark, I wouldn’t have been able to tell, but I’m still proud as heck of myself for going through with it.
40. Life Is Full of Surprises
I’m laying on a hospital gurney. My wife is sitting next to me. I’m in the Emergency Room of the hospital where I have been listed for a heart transplant, but I’m there because my bowels are obstructed. I’m very calm because I know what’s wrong with me. I’ll be admitted for a couple days, put on a liquid diet, and my intestines will get back to normal.
However, being on an artificial heart requires that I go into the hospital for every little thing that comes up. Suddenly, my main cardiologist pops his head into my ER room. “We have a donor,” he says. I’m shocked, but elated. What are the chances that I’m there when the call comes in? Then he tells me the bad news: it’s a very high risk donor. The individual had died of an overdose. My wife looks at me. I think for a minute. I said “Screw it, I’m doing this.”
That was on the 1st of November, 2014. Within six hours, I had a new heart. No complications. No infections. No problems. I spent 16 days recovering, and then I finally left the hospital. After a couple of weeks, I drafted my thank you letter to the donor’s family. I sent it off through the New England Organ Bank via my hospital. Two weeks later, I received an amazing call. My donor’s family wanted to meet me.
I learned something very surprising while talking to them. It turned out that my donor didn’t die from an overdose of any kind after all. He actually fell and hit his head at work. The hospital said that it was an overdose because his city had so many of them. It turns out that he didn’t tell anyone in his family about having hit his head at work. He didn’t think it was a big deal. He just ate dinner and went to bed. In the morning, his grandparents couldn’t wake him up because he was in a coma from a brain bleed.
I’m five years out now and doing great. I get together with my donor’s family all the time. We hang out, and even do birthdays and holidays together. We even get together just to talk about my donor from time to time. They are truly wonderful people. So after all that, I threw caution to the wind and risked my health in an attempt to save my own life. Not only did my risk succeed in doing so, but it also helped connect me with some very special people who have found new meaning during a tragic time in their lives as a result.
41. Fight or Flight
I was a flight nurse at a company that liked firing people. We were transporting a patient from a car accident who became pulseless. Per policy, we had to go to the closest hospital. Our closest hospital was nine minutes away, however I knew that this hospital was tiny and couldn’t care properly for our patient. Just 13 minutes away was a trauma hospital that would definitely be capable of handling his needs.
Our patient was dead and, statistically speaking, was likely going to stay that way. There was only one way to revive him, but it would mean breaking all the rules. I threw caution to the wind and told the pilot to go the trauma hospital, knowing full well that this would be reviewed and that I would probably be fired for violating policy. Fortunately, the trauma hospital did a fabulous job and the patient actually survived. I was reviewed, but not fired.
42. Not Gonna Take It Anymore
At one point during my childhood, I was going through some domestic violence nonsense and I wasn’t allowed to leave the home for months at a time. My parents choked me, yelled at me a lot, etc. I can’t remember all of it. My grandmother had passed on and I’m sure they had an awful plan. I think their intent was to off me so that they could keep my part of the inheritance.
The inheritance money finally came in after about six months of this treatment. While my parents and other siblings took their portions and went on vacation, I decided on the spot to take my part and buy a Greyhound bus ticket to get the heck out of there and away from my horrible family. Easily the best decision I have ever made.