"I Asked My Boss Out": People Are Sharing The Times They Decided To Shoot Their Shots, And How It Turned Out

    "After 12 months of no contact, I sent him an email professing my love and offered to move back to Canada for him."

    Asking someone out on a date or telling your crush that you're into them can be pretty scary. Sometimes we all just need a little inspiration. So when I asked the BuzzFeed Community about the wildest risks they've ever taken, I was thrilled that many of the responses involved romance!

    So, since Valentine's Day is upon us, here are some epic stories of people shooting their shots:

    1. "I saw a super-attractive guy at a massage parlor. Slipped a note in his shoe: 'Taylor Swift, 6th album, 8th track, :48 seconds,' and then listed my number. The song reference? 'You’re so gorgeous / I can’t say anything to your face.' He texted me, but things fizzled out."

    2. "One month before graduating university, I was at a party. In walked a guy I had met three years before through mutual friends. I'd had a crush on him since we met. A thought crossed my mind: 'What do I have to lose?' So I jumped off the counter I was sitting on and went right up to him and his friends. We talked until 3 in the morning, sitting on the bleachers looking at the stars. We’ve been together eight years and married for four. I married my crush!"

    Couple under starry sky hugging

    3. "I asked out my co-worker who I had a crush on. He said yes, and we went on our first date. We were having fun, but he said he wasn't sure if it was a good idea since we are working together. We decided to give us a chance anyway. We've now been together for three years, and living together for one and a half years."

    "I now know he's the love of my life."

    sarahr4591f68ee

    4. "A cute guy posted a selfie in a Facebook group we were in. I commented, telling him to slide in my DMs. Two months later, I moved across the country to be with him. Now we're living our happily ever after."

    5. "I asked out my boss on our last day, five minutes after the official end of day. He said yes. Then he ghosted me. I was fine with it, and then my best friend unknowingly moved next door to him. We only found out after she signed the lease. So we see each other all the time and avoid eye contact as much as possible."

    6. "I got tired of the dating scene in the States and decided to take a chance on someone international. I met a Venezuelan living in Colombia, and was set to fly there last year but couldn't — thanks, COVID. In a month, I will be going there to meet her, and we are working on the massive amount of paperwork for her to move here after 18 months of virtual dating."

    Beautiful sunset over Cartagena, Colombia

    7. "I knew this girl for about three weeks. We were 'talking,' and I asked her if she wanted to come over and make out. Our 13-year anniversary is next month."

    ryana4764f34c6

    8. "I moved to Canada for a one-year working holiday and became friends with this one guy. We liked each other, but were already dating other people. Then I decided I didn't want to pursue it because he was older, we were from different countries, and my visa was almost up. I spent a year back home trying to forget him, but couldn't. After 12 months of no contact, I sent him an email professing my love and offered to move back to Canada for him. Eight months later, we got engaged."

    Man with face mask embracing and lifting his girlfriend at airport terminal

    9. "In high school, the cheer team was selling holiday grams, a piece of chocolate, and a little note you could write. I sent one to my crush, a guy in my science class. I added a little Christmas pickup line and my number. He never spoke to me again."

    10. "When I was 11 years old, I had the biggest crush on my older brother's best friend. This crush lasted over 10 years, and he was always in the back of my mind, even while I dated other guys. One day years later, we were on the phone, and he asked, 'How come we never dated?' I couldn’t believe he asked me that, and I knew it was my one chance to say something — I said, 'Because if you dated me, you would end up marrying me.'

    "Six months later, we were married. We will be celebrating our seven-year wedding anniversary this summer."

    —Anonymous, 26

    11. "In late 2015, I finally worked up the courage after consuming three bottles of wine to tell my best friend of a few years I was in love with him. I mean, this dude had been there for me through some rough shit and seen me at my worst — I was so nervous, working myself up in my head about how I was probably reading too much into his friendship, but I couldn't let my feelings go unsaid any longer. I can't remember what I even said, but being blunt must have worked because I proposed to him in 2019, and we're rounding out our second year of marriage in 2022."

    12. "In college, after a really rough nine months of transferring schools, losing my mother to cancer, having a major surgery, and my then-boyfriend breaking up with me, I developed a crush on the smartest (and cutest) guy in my major. We had a couple classes together and were in a related club together. And I had a feeling that he liked me too. It was the week before final exams, right before summer break. I made him a little art project related to his favorite sport. I am not artistic at all. Anyway, I slipped him that gift after class one day. We had our first date the next week. Nineteen years later, we are married, with a couple of kids. And one of our kids is playing dad's favorite sport."

    eds99

    13. "I found my person through Instagram. After four years of a long-distance relationship, I moved from the UK to the US, and we have now been together for eight years, married for four. Sometimes, I forget how big of a deal it was to pack up and leave everything."

    14. "Started dating a guy, and it was intense. I knew he was the one straight away. About a week after our first date, I had a dream that he proposed to me, so I threw caution to the wind and just told him about it. Luckily, he said he felt the same way. He proposed for real two weeks later."

    "Eighteen years on and we’re still going strong."

    pritchette

    15. "I left my husband for a famous Vine star in another country. He approached me on Instagram, and we hit it off instantly. The risk didn’t pay off — he turned out to be a manipulative loser. I regret wasting my time on the Vine star, but I don’t regret leaving my husband."

    Gurki from "Dating Around" walks with a smile through New York, happily single

    16. "About two weeks into my new job, I noticed there was an unspoken attraction between my boss and me. After days of electricity every time we were near one another, I finally took my shot and said, 'Hey, I'm going for a drink after work. Are you coming with me?' He smiled and said, 'Hell yes!' Turns out, he was worried about asking me out because he didn't want me to feel pressured since he was was my boss. Fourteen years and five kids later, we are happily ever after married!"

    "If you have something potentially great to gain, always take the risk!" 

    —Anonymous, 36

    17. "When I was 18, I was working a summer job at a local restaurant as a waiter. It was a super-busy Friday night, and I was running into the kitchen to pick up a few orders. I was distracted by the chef, and I ended up running into the dish boy, who was carrying a huge stack of dishes. The dishes fell from his hands and shattered all over him. There was silence. I was so mortified. Then all of a sudden, he started laughing. And I joined him. We are now engaged, and I can’t imagine being with anyone else!"

    18. "I swiped right on this guy on Tinder. Two months later, I flew 3,000 miles to meet him in person. A month after that, I packed up my stuff and moved across the country into his room. Five years in, I found out I had breast cancer at 26 years old. He stayed by my side the whole time. Two years later, we had a little pandemic wedding, and one month later, we found out I was pregnant. We took a risk, rushed into a completely impractical relationship neither of us were ready for, and with lots of hard work, it paid off."

    19. "I was 9 years old, and she was 17. She was my neighbor, and I was absolutely in love with her. I still consider her the most beautiful woman ever. One day, I asked her on a date to the zoo. She smiled and told me yes. I was thrilled. I told her that I was planning on eight weeks from when I asked her, so I could save my allowance. I even asked if she minded driving. She said she could drive us. I thanked her, and told her that I'd come by at noon to pick her up eight weeks from then. I checked in with her weekly to make sure she was still wanted to go. Eight weeks later, I knocked on her door wearing the nicest clothes I owned as a 9-year-old boy and asked her if she was ready to go. She told me that she thought I was joking. I burst into tears in front of her, ran home, and cried for hours."

    Jonah Bobo and Analeigh Tipton in "Crazy Stupid Love"

    20. "After speaking for only a couple of months on Facebook, I flew to Egypt from the US to meet my boyfriend in person. We had been Facebook friends for three years, and at first it was nothing more than a quick hello and small talk — some of the women in our family knew each other a little, and encouraged us to get to know each other. After those couple of months, I flew to Egypt for two weeks...and we got engaged. I filed for the 90-day K1 visa, and we got married 14 months later. We now have two beautiful kids, and it was the biggest, most beautiful risk I ever took."

    A bride and groom in the sunset

    21. "The night we met, he spilled a beer in my lap. He tried to give me money to get my clothes cleaned. Before I knew what I was even doing, I slid the money back over and said, 'Save your money. Take me to dinner.' We went on our first date three days later."

    22. "I dropped everything and moved to Italy to be with an Italian boy, frolic through vineyards, and Eat, Pray, Love for life. I ended up back home less than a year later, single, broke, and covered in mosquito bites."

    ericaeulerax2y

    23. "In my late 20s, my fiancé broke off our engagement. I wallowed in my depression for several months. One day, I was headed to work and got on the elevator. Kim, a cute woman who also lived in the building several floors above me, was inside. We'd spoken to each other and knew each other, but hadn't ever really talked. In that moment, for the first time since my fiancé left, I felt an attraction. It was like I was seeing Kim for the first time. We ended up talking in the elevator and walked to the parking lot together since our cars were just a couple spaces away from each other. There was definitely chemistry. As we were leaving, Kim said, 'Wish me luck. Today's gonna be rough.' I said, 'Well, you're in luck. I make terrible margaritas, but they have tons of tequila in them.' She laughed. It was the first day in months I'd felt a glimpse of happiness. When I got back from work, I parked my car and saw Kim's car drive behind mine."

    Two margaritas on a ledge over water

    Did you ever "shoot your shot" with a crush? How did it go? Let me know in the comments!

    Note: Submissions have been edited for length and/or clarity.