People Share Their 'Wish I'd Done This Earlier In Life' Stories

Rewarded with a Trip to Italy

"I was a young Airman at my first base in California and I worked with a girl (let's call her Sarah) who was way more attractive than anyone my small-town Missouri a** had ever hooked up with before."

"For some reason, she was into me. She was into a few other dudes too, but at the time it didn't matter because I was 19 and stupid and she was a few years older and far more sexually experienced than I was. We had sex a few times and sort of 'dated,' but it didn't really go anywhere and I was heartbroken but cool with it."

"This was right after 9/11, so U.S. military operations were starting to ramp up and Sarah got deployment orders. They didn't tell her where she was going, but she was on the hook."

"Her reaction to the news was to tell our Chief that she was pregnant with my kid so she didn't have to go. I knew she wasn't pregnant and just using it as an excuse not to deploy."

"The Chief came to me and asked if I'd go in her place. As I said, I was 19 and even though I was a little scared, I signed the dotted line and told him of course I'd take the deployment."

"It turns out, the 'deployment' was to a NATO base in Naples Italy where I'd be paid about 80 dollars per day per diem on top of my normal paycheck."

"As soon as Sarah found out where I was headed, she called the Chief and told him she wasn't pregnant anymore and would like to take the deployment."

"The Chief denied her request and I spent an amazing eight months in Italy, being paid more money than I knew how to spend and having the time of my life."

- NewPac

Watching Them Move On

"We met thru work and dated for one and a half years. She cheated with another coworker who is married. We broke up. She started to date a different coworker. Not the married one. She paraded that relationship in my face."

"Everything was great until it wasn't. It really f**ked over my self-esteem and self-worth for years. It sucked that I had front row seat to her moving on."

- bluevacuum

"I feel that last part. When my ex moved out, she did it slowly over the course of like a month. She came over every day and packed up slowly until she finally got everything."

"The worst day was when she finally came and took her cat. I still remember sitting in front of the door and crying for hours after she left that day."

"There's a band called Pedro the Lion that has this lyric, 'My old man always swore that hell would have no flame. Just a front-row seat to watch your true love pack her things and drive away.'"

- FTG_Vader

"When I kicked my ex out this summer for having cheated on me, I gave her an arguably unfair timeline to leave before all of her possessions just went outside, and packed and moved everything for her to the garage overnight, since I couldn't sleep anyways."

"This is why. I simply couldn't handle those constant reminders and wanted it done and gone as fast as possible."

- DeceiverX

A Messy Breakup

"I had resigned and was leaving the company anyway but it was one of those classic hookups at a company party. We had fun for a while but then she decided to stop seeing me."

"I'm glad I had left the company by then; otherwise, things would have been messy."

- love_boobs_in_dm

A Huge Theft Ring

"I got fired and she got fired and all 20 guys she f**ked while we were dating were fired."

"I got fired under false allegations because she was my girlfriend and she was stealing from the store."

"She got fired for stealing from the store."

"The other 20 were fired because it was brought up that she was stealing and sleeping with managers and other coworkers while in a relationship with me. They thought that me and her were the center of a theft ring."

"Like, no... I don't steal so."

- butahoomach

A Promotion for Everyone

"So my wife of over 10 years, who had cheated in the past and I forgave her, got a huge promotion at work which caused us to relocate."

"I guess she got tired of me because she kicked me out and we were getting a divorce."

"Four months later, I found out that a co-worker had a thing for me, so I took my shot. The sex was amazing. It could be that it’s been a long time for me since sex with the wife was basically non-existent for the last few years of marriage."

"Me and the co-worker have now been dating for over a year and I haven’t been happier. So for me, it worked out for the best. And the sex is still great!"

- Unrealevil360

Too Many Options

"I worked at a casino as the only male cocktail waiter/bartender (roughly eight cocktail waitresses and four female bartenders). The floor was mostly women between the bar, servers, restaurant, and dealers."

"I slept with one of the cocktail waitresses for a couple of months even though I knew I had a bigger crush on her than she did on me. I also knew I didn't really want a relationship with her for a couple of reasons."

"Evidently, she told some people and gave me good reviews. After she quit and moved away, I had more interest than I really knew what to do with and kinda just went for it with anyone who showed interest that I was attracted to as I knew I had no more than a year left there no matter what happened. I ended up with four more of them over the course of a couple of months."

"One time on a shift, I looked around and all four were on the floor somewhere. All knew each other but I'm not sure any knew about the whole situation, and none were any false impressions of a relationship as far as I know so nothing bad came of it."

- CallMeLargeFather

A Family Man

"Not me, but she was working in payroll and he was a security guard. One day, a coworker saw the security guard walking her to her car. Immediately, she was transferred to another branch. However, they continued to see each other."

"Soon after, they got married after finding out she got pregnant. In the next five years, they had three daughters, with me being the youngest. My dad ended up passing away from brain cancer when I was just a toddler."

- Swimming-Site-7682

The Downfall of a Friendship

"I had one good experience one bad. The first one we ended up dating for a year and a half. We had a ton of fun sneaking around at work, and even though in the end he totally broke my heart, it wasn't a bad experience."

"The second one was very bad. Do not recommend."

"I thought he would be safer because we were friends, so I figured communication and rules would be no problem. Instead, we didn't communicate at all because we were both so worried about hurting each other's feelings."

"It ended badly with major assumptions on both ends and now it's very awkward and uncomfortable."

"It makes me sad because honestly, I just miss my friend. While the experience can be fun, I don't recommend it."

- laylalove89

A Suspicious Relocation

"Pretty fine. We worked at different locations in the company the first time we slept together, but we knew each other as she had trained at my location."

"One night we ran into each other at the bar and one thing led to another. A couple of months later, I ended up getting transferred to the location she was at and we just acted like it never happened."

"After a month or two of working together, we ran into each other again at the same bar, and history repeated itself."

"There was a slightly awkward moment a couple of days later when I had to find a way to give her back the necklace she'd left at my place without anybody noticing, but other than that, our working relationship didn't change at all."

- Nervous_Chipmunk7002

Messy Feelings Everywhere

"First time: super fun but I got more attached than she did."

"Second time: kinda fun but she got more attached than I did."

"Moral of the story: don’t f**k coworkers unless you’re SUPER SURE."

- Arch021

A Heartbreaker

"We dated for over a year and then one day she randomly decided to break my heart. Thankfully, we had stopped working together by that point. It still makes me tear up thinking about her, though."

- Electronic-Mud1634

Best Decision Ever

"We had an instant connection the moment she joined the foundation I had been working at for a year. We worked at the front desk together and we got to know each other very quickly."

"Neither of us enjoyed small talk and we would get angry emails from our unbelievably incompetent manager about the amount of laughter coming from the front desk. We got all of our work done, and then some, our manager just felt like she was getting left out. Which our manager was, but it was because she sucked."

"I worked from home four days a week before my new coworker started and a few weeks later she asked me why I was coming in every day. I told her something about training her how to answer the phones, which she instantly knew was bullsh*t (we got four calls a day, max)."

"The first time we hung out outside of work we told each other it would be a terrible idea to date. That lasted for about 10 days. The next time we hung out we slept together."

"That was a year and a half ago."

"We left the foundation after she told our manager that her 'management style' was untenable in an email. The two of us then called a meeting with her and we laid out a very well-planned strategy for departmental growth and change."

"Our manager nodded her head the whole meeting and told us how proud of us she was for taking ownership of our careers and how excited she was to implement our new plan."

"Three weeks later, they fired my coworker. They pushed me out, telling me that they no longer had a place for me (at my review the previous year, the CEO told me herself that she believed I had CEO potential)."

"We both have new jobs, she is a high school English teacher at one of the best high schools in the country and I became a private investigator."

"Her dad and I go to college football games together and our moms get lunch and do spa dates."

"We have been showing each other how to heal and grow as individuals and as partners."

"Right now, she's sleeping in my bedroom while I type this in the living room. I don't know what the future holds for us but I do know that she's the love of my life."

"Sleeping with my coworker is the best thing I've ever done."

- frankenfine305

"Marry this girl already."

- Long-Regular-1023

Redefining the Coworker

"Pretty good. We have a kid together. Granted we'd been married for seven years before we became coworkers."

"She always wanted to teach at the same school as me. The school grew enough that it needed a dedicated English teacher. She has a master's in it so it worked out."

- i_have_seen_ur_death

A Slow Transition

"We worked together for a couple of years and became close friends before we crossed the romance line one night after a lot of drinks. Honestly, it was and still is amazing. Happily married now over 15 years with two kids."

- theshannons

A Bartender's Love Story

"She's sleeping next to me, cuddling our cat."

"Turns out our chemistry working behind the bar together was also amazing outside of work."

- Eb_Ab_Db_Gb_Bb_Eb

We've all heard that love and work don't mix, and that we absolutely shouldn't get close to our coworkers, but from these Redditors, it seems that while things could get messy, sometimes it's worth the risk.