As well as the odd bandit, lottery, Omaze house draw, I do occasionally have a flutter on sport. But I couldn't tick the most relevant option for that as it mentions two 'sports' I would NEVER fund through gambling.

I have gambled on getting home by BEING ON the last train. My wager was far too much agreeable red win with friends in Taunton. I fell asleep and missed my stop. I wanted Bristol TM, I 'won' Birmingham NS. My 'prize' cost me a night in a hotel.

 
Votes from me:

Premium bonds - my wife and I have a few, only because our respective parents bought them for us, over sixty years ago, when it was fashionable to do that. Neither of us has received any actual cash benefit from any of those bonds, ever.

Carefully selected investment funds - my wife and I have some of those, through our respective personal pension plans. Those were recommended to us by our independent financial adviser at the time (nearly twenty years ago) and they have performed generally well, over the years.

We stopped doing the lottery many, many years ago, but I have occasionally bought a raffle ticket - generally in a work environment, where it's sort of expected that staff will support it, rather than in any real expectation of winning something. My wife, too, bought a raffle ticket in her own workplace recently - and won something!  A bottle of male shower gel - which she promptly gave to me.

I would not gamble on 'getting home at night'.  Over the years, I have experienced two occasions when my late night return journey home to Nailsea did not work out. On the first occasion, I walked (it's nine miles). On the second, I was put up on their spare bed overnight by a 'good samaritan' in Bedminster - to whom I am eternally grateful (I had enjoyed a few drinks on that occasion.) 

CfN. 

 
I've got a few Premium Bonds knocking around that I've had since I was a teenager/twentysomething....not won a penny.
I still have my annual flutter on The National and I'll cross a road if the approaching traffic is far enough away for me to feel comfortable with.
I'm pretty certain that I've caught the last trains home in the past without worrying too much about it but I'm a bit more wary now.... the train I'm on as I write this was chosen rather than the later one with that consideration partly in mind.

 
Premium bonds are a bit of fun but statistically even with the maximum holding you're better off with an ISA in terms of likely returns on your money.

I'll have an occasional flutter on sporting fixtures just to add a bit of fun if I'm attending!

 
Most items: definitely not - because on average I'm going to lose out to the bookie etc.
Premium bonds and carefully selected investments: yes - because the average gain makes them worthwhile.
Crossing the road in front of oncoming traffic: usually - but only after looking both ways twice and because I reckon I'm still nimble.
Depending on the last train: yes - because I expect the train company to be able to get me home eventually.

For the Greatest Gathering I did risk getting the last train home from Derby to Cheltenham.  Because I really wanted to stay on for the Museum of Making evening slot, and I reckoned that the worst that was at all likely to happen would be having to get the first train the following day.

 
I've got some Premium Bonds and so has Lisa - it's a way we can have some funds off to one side for emergency use in separate accounts just in case one of us becomes no longer available and the other has to pick up the pieces.  And I will occasionally buy tickets for a prize draw; I will admit to that being either to support the old cause the money goes to, or because it's expected of me.  I will not gamble on going out and taking a punt on being able to get home if it's in doubt - in other words I will not take a significant risk in being stuck, unplanned, away from home.

Last night (and far from the first time), GWR cancelled but then re-instated the last train home, and that would have put me personally off even risking an evening out.  Sure, the train ran, BUT I wouldn't have risked it.  Posting a poll here to see if I'm unusually cautious on that, or if others would gamble being able to get home.