There are two types of pain to deal with when gambling and losing.
1. The first one is the money you risk and lose.
2. When the money you almost win is very big.
I want to share my opinion by explaining this.
Like the first one it's just like you are a single person you don't have any girlfriend so it's will hurts when you are seeing the others with their girlfriend.
And for the second one it's just like that you was a single person and then you found one girl as your girlfriend and then after some days the girl cheated on you and also break up with you. So obviously here this one will be more painful for you and all the peoples.
Just like it is I also have the same opinion like the others already given in this thread that second one is more painful. Because it gives us hope and then takes that hope away.