Let’s set the stage. You flopped a strong draw, such as an open-ended straight or flush draw, and called a bet or two in position against one other player. When the river comes, it doesn’t bring your draw. You’re holding a busted hand, and your opponent checks to you.
What do you do?
Of course, you have two clear options here. You can check behind and go to a showdown that you’ll most certainly lose, or you can make a bluff and try to steal the pot.
Weighing Each Factor
Just as with most things in poker, there’s no right or wrong answer to this question, at least in general. You need to weigh each factor, think through the possibilities, and, essentially, make a cost-benefit analysis.
The first thing that you need to think about is ranges. Start by working out your opponent’s range, beginning with any pre-flop action and narrowing it down based on the board run outs and their bets. How many high pair or two pair combos do they have? Could they also have a busted draw? Do they have any nutted hands? Is it polarized or merged? Once you’ve got them on a range, think about your own range, using much of the same logic.
If your range contains a lot of value and not a lot of bluffs, then it’s almost certainly correct to bet here, especially if your opponent has a lot of thin value. Also be sure to check if other draws besides the one you’re holding came out on the river—if you’re holding a busted flush but the river completed the straight, then your bluff may have more credibility.
You’re also going to need to assess your opponent's psychological profile based on your previous observations of them. If they’re a calling station who will call a shove with low pair, then you probably don’t want to risk any more chips. If they’re a nit, on the other hand, you can fire with impunity, knowing that you’re getting plenty of fold equity.
Another consideration is bet-sizing, which, again, will be informed by whether you can exploit an opponent and the action in the hand. However, your default is to make a small sized bet, around half-pot. This bet sizing is commonly used in value betting because it’s easier to call. If you’re playing against a savvy opponent, they may recognize it as a value bet, consider themselves beat, and give up the hand.
Of course, we can factor in everything from relative hand strength to stack sizes as well.
Even after you make these calculations, you still don’t want to do the same thing every time. To make it harder for other players to exploit us, we usually want to play a balanced game. If you always bluff in situations like this, then keen observers will pick up on this fact and call you down every time.
In summary, you want to think through all the information that you’ve gathered, make a careful analysis, and then weigh your options accordingly. If it’s almost certainly correct to bluff, then you may want to bluff 80% of the time and check the other 20%.