take a gamble
try one's luck
take a risk
chance
take a chance
go out on a limb
chance one's arm
take a flutter
roll the dice
lay on the line
gamble
tempt fate
run the risk
disaster waiting to happen
triable
throw caution to the wind
venture
high-wire
have a stab
riskily
riskable
venturesome
attempt
put one's ass on the line
high-risk
venturer
adventurer
risk
run a risk
dare
adventure
take chances
daring
candle in the wind
hazard
razor's edge
imperil
audaciousness
give something a try
bell the cat
bite of the cherry
retry
assay
safen
give something a shot
live dangerously
bid
fair go
stick one's neck out
forlorn hope