What are some of the more significant gambles you've made in your life?

I bet against Pascal

So far, so good.

I don’t bet very often, really, metaphorically or metaphysically.

I’ve made so many. Loads were dismal flops, some turned out great. I am about to take another. I guess I never learn.

I bet on the football (soccer) on the weekend.
£2 bet.
Mainly becuase it makes the scores more interesting.
The most I’ve won is £73

Apart from that i don’t really like gambling.
I’ve grew up watching my dad loose at lot of money because he gambles a lot.

I play it fairly safe usually, but when I do gamble I take precautions. I gambled on my driving skills a lot as a kid, but I always had the seat belt and shoulder harness pulled as tight as I could. That way when it bit me in the ass I could walk away.

One time I got the doubling cube all the way up to 64 with the AI set at Expert, and won. I’m a bit obsessed with backgammon.

I left an almost 22 year marriage 10 years ago and jumped off the cliff of financial and personal security, to save my soul and sanity. it was a gamble, and I won the jackpot of renewed sanity. lol

I emigrated from the UK to Australia with £300 in the bank. It all turned out fine.

I proposed to my (now) wife after we had only been dating 6 weeks. That was 26 years ago.

@majorrich Good for you!
@Bellatrix Good for you!
Actually I should be saying good for you to all you jellies. Congrats on having the balls to take some risks.

I used to go to school in a rural area and I drove down long straight or gently curving roads with no traffic on my way home. I had never seen a cop car on my ride home, ever. One day, having a new car, I decided to see how fast I could get it to go. I gunned it up the hill towards the long straightaway, and went flying over the top—literally—wheels in the air.

Of course you know how this story goes. No cops ever? The first time I am flying—going about 90—and you betcha, there’s a cop coming the other way. I’m far down the road when I see him pull a U-ey in my mirror, and turn on his flashing lights. He’s far enough away that I decide to try to get away.

I slam on the brakes, leave rubber on the road as I fishtail into a left turn, and go tearing down the hill towards the lake. In a quarter mile, there’s a Y, and I can’t decide which way to turn until the last second, and as a result, I nearly roll over, but instead slide my care in a 180, and stalling.

Frantically I try to get the car started. I’ve got it started and have just started moving when the cop comes down the other way, hesitating as he passes me, and then continuing on.

Gambling makes me too nervous to be any fun for me. Like they say, the safest way to double your money is to fold it over once and put it in your pocket.

I gave up my job and moved to a new city with a man I met a couple of weeks ago. My son and I loved his rented beach house, and we lived happily ever after. We will be celebrating our 38th anniversary this year.

Marrying an Englishman.

I gambled with my prostate. I bet that the cancer was completely contained in the prostate even though my numbers were very high and there was a more than even chance of it having spread. To play that bet, I elected surgery rather than chemistry or radiation. I doubled down 18 weeks later by betting I did not need radiation.
It’s been over 3 years and my numbers are perfect. All the rotten cancer ended up in a hospital hazardous waste bucket.
I am a lucky guy!

Related to @zensky‘s question, I gambled on a marriage. Pretty much lost that one, only win was getting my great kids.

I’m not much of a gambler. I think it relates to the fact that I hate waste. If I gamble and lose then I’ll have wasted time, maybe money, energy, on something that didn’t gain me anything. As they say, “Nothing ventured, nothing lost.”
But I did take a chance on my last job move. I changed into a different design area than I had been, something new and challenging and something I wasn’t at all certain I’d enjoy or be any good at.I had a long learning curve. I took an enormous pay reduction because I had no experience. At first I hated it, then I loved it and got passionate about it and obsessed with it. I got promoted and my pay inched up bit by bit. I took classes and learned how to draw on the computer. For a while things were good, not great, but good.

Now things have changed and in the end I think I’ve been cheated of what I deserve. But all in all, it was a good gamble….just wish it didn’t take me so long to get where I am. Plus the salary being so bad in the beginning sucked the life out of my 401k. I don’t have much to retire on and have to play catch up. In the end I feel like I’m not sure if it was a good decision or not. In the end, does it really matter? I have learned a lot. I guess I’ll do what I always do, whatever it takes to survive.

Marrying my second husband, after I swore I’d never get married again. I was terrified…he asked me 5 or 6 times before I finally said yes. Seven years later, and it’s still a winner.