What was a moment when you said, Screw it, Im going for it?

35 comments

  1. Decided to quit my job, pack a suitcase, and get a one-way ticket to Japan with no job or visa to meet a girl.

  2. Matched on a Dating app with a coworker who works on a different shift . Experience has thought me, Regrets hurts more than Rejection. So far, I have been ignored but I feel more at peace that I let her know I liked her. When I look back on it, I won’t feel sad that I was scared to go for it, and not sure if she would have said Yes.

  5. Quit my job without one lined up because my boss was such an ass hole. Best decision I’ve made in years, though I recognise this easily could’ve gone very wrong.

  6. Let go of that “she’s out of your league” self-doubt crap and confessed my feelings to a woman 10 years my junior (25 to my 35 at the time) and asked her out. She said ‘yes’!

  7. There have been a few times when I’ve approached girls to introduce myself that have been harder than jumping off a cliff into the ocean tbh

  9. Fighting my bully back in high school. Fucker had a lisp sounding like Sylvester from Looney Tunes and as well as his older brother that went there too (all male hs). Would constantly talk shit about me being a pussyless loser and being a lame. The last straw was when I went to get breakfast and came back to see the notes I was taking for a test were all scribbled on. Yeah, sure, there was no way for discern that *he* did it. But it gave me the fire to fight him during PE.

    Got my ass kicked, 5 days of ISS and my bottom (inside) lip cut, but it felt fucking good when that right jab connected. Being in a cesspool of testosterone where guys don’t do shit but play sports and cheat, you kinda had to win a fight for be dope at sports for people to really *see* you. I lost, and I wish I knew how to fight since my dad commented “You play all those games and you don’t know how to fight?” as if he forgot the boundary between fantasy and reality.

  11. Accepting a job with an old mentor after I left the industry he trained me in.

    3 floor building. 3 different restaurants: cocktail lounge in the basement, fine dining on the main floor, street food style pub on the rooftop.

    Reignited my confidence and love for my trade.

  12. Decided at the beginning of a recession to give up a career and go back to college. I had saved a bunch of money in the year leading up to this decision and had paid off my car. That ended up saving me as I went through periods of being jobless and on unemployment for the first time in my adult life and lived off savings.

  13. Laser hair removal. Had to make the call that I was never going to want facial hair. I’m a few years in and don’t miss the stubble.

  14. Got married to a woman halfway across the world. Despite the difficulty of all of the immigration stuff, she is the only one who has ever treated me like she wants me specifically and not just generically wanting to date someone.

  15. I was working various jobs in NYC for about a year. One rainy August night I was doing deliveries on a bike and i crashed into a pedestrian. Neither of us were badly hurt but it was enough to knock me off my bike. I laid in the street for a second contemplating life. I hated manual labor. I hated being paid so little. I hated the impatient customers. So I said fuck it i am going back to school. I signed up for xray school literally 2 weeks before college registration deadlines came. About 3 years later I completed my degree. Now I’m working as an xray tech. Best decision I’ve made thus far.

  16. Asked out a friend I had a massive crush on, she politely declined but I’m still glad I told her the truth and we are still great friends

  17. I broke up with my girlfriend and decided I would go after the woman I really wanted, but was nervous about.

  18. Traveled to the other side of the world for love. It was definitely a gamble – we barely knew each other when I went, but we were an item when I left. Long distance took its toll (especially because of the pandemic) and we’re no longer together, but I have no regrets.

  19. 22 , bought a little lot in my town , built a 900sq’ building on it (myself)…..I had a carpentry background…..opened a short order Cafe , milk shakes , ice cream , smoked my own BBQ , delicious steak Sammiches 😋 had 7 employees….was a huge success…..then divorce hit….couldn’t keep it going , had to move on in life…greatest experience ever , taught me alot 😉

  21. Left my home and home state to move across the country to go to grad school and pave my own path. Don’t regret it in the slightest.

  22. Changed jobs and Moved to another state and lived in and out of hotels for six months to help my parents’ business despite deep reservations about working with family.

  23. I went about four years without even trying to date (or even get laid) after a relationship ended badly enough to make me think I’d never be able to trust a female human being, ever again. I honestly thought I might literally never have sex again, and I was kind of okay with that.

    The moment came when I developed an enormous crush on a new female friend, found myself alone with her, and she just kind of… *very deliberately* maneuvered herself into a very kissable position.

    I was like, “Welp, so much for being celibate for the rest of my life.”

    It was just a fling, but it got me out of that whole “avoid intimacy at all costs” phase, and I never went back into it.

  24. Was made redundant from Multiyork in Dec 2017. Sold most of my shit, packed as much of what was left and moved to Switzerland to be with my then girlfriend.

    Had no real job, wasn’t sure I’d get a visa or work permit, had £50 in my bank account. Been here 5 years now and I’m married.

  25. First time I decided to be a dominant male.
    I swallowed hard, said fuck it. approached a hot chick with a macho confident overpowered machismo attitude, used every alpha male line I had ever heard and stood stall firm and overly confident.

    This chick was completely mesmerized by the end of the night.
    But I couldn’t keep the act up past the 6th month, lol.

    But it was wild to feel so powerful, confidence can go a loooooooooong way in life.
    “Take no bullshit” attitude also ended up giving me power over her friends and sisters.
    It was getting a little weird to wield so much power. ha ha

    But it was too much work though, I honestly don’t know how some guys can be wired that way in real life.

    Being a shy person, I swallowed my pride hardcore, hell, I even got like raises at work during this time to keep appearances (just from being commanding and bossy) and my boss even thought I was a new man. ha ha

  26. When my friend broke up with my big teenage love after being a douche to her. (I was in love with her before they got together)

  27. Two months ago, after a years long toxic relationship with a narcissist, I decided to put myself out there. Saw this gorgeous redhead who was talking to a friend of mine and went to approach her just to start a Convo. She immediately hits on me. She gives me her number.

    I’m usually pretty okay in terms of looks, but I rarely go after gorgeous women. I decided to just be straight with her and within a week we slept together, and it SHOT UP MY CONFIDENCE.

    The best way to get over one woman is to get under another one. Had I not approached I wouldn’t have had my best lay in years.

    She was poly, so it was merely a 1-nighter.

  31. End of the school year I asked my crush for her number. Never amounted to anything, but it was a nice feeling.

  32. Halloween night. When I decided I won’t let anyone treat me like shit anymore and cut a lot of ppl out of my life. I honestly feel more at peace not having to beg for anyone’s attention and I’ve started working out, currently lost 16lbs and I got another 16lbs to reach my weight goal.

    I used to be terrified to be alone and its not so bad, I love it!

  33. I’ve had a lot of those moments.

    Most recently moving back to my hometown and buying a house. Right before that I started working for myself, and that turned out great. Got a divorce before that, which turned out to be a catalyst for all kinds of good things.

    But I have rarely said no to most opportunities. I just picked up and moved to California when I was in my 20s.

    Always take a chance. You never know what might happen.

Leave a Reply
You May Also Like