Do you ever enter contests? If so, which ones?

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Could be anything from raffles to product giveaways to lotteries...

[HipChick]

1. sweepstakes...biggest prize was a car

had to pay taxes on it..

[femmocrat]

2. I play the state lottery in a pool at work.

I've been playing for years, but the most we ever won was about $2000 (split 13 ways).

[MrSlayer]

3. I play powerball and other various lottery games.

In a half hour I'll be $190 million richer.

[dembotoz]

4. enter various contests if the mood hits and the prize appeals

somebody has got to win it.

Couple years ago taking my kid to a hockey tournement he was playing in.
His hockey bag died just before we left and he ended up taking his gear in a suitcase--much to all his teams amusement. Raffle at tourney--I won the kid a new hockey bag..
worked out rather well

[Old Troop]

5. I buy lottery tickets from time to time and then never check whether

they're winners. Mentally spending the prize money for weeks is the cheapest entertainment I know of.