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.