I think this is exactly what you want:)
int hitcounter = 0;
int lastHint = -1;
while (!GameOver)
{
Console.Write("Answer: ");
string answer = Console.ReadLine();
if (answer.ToLower() == "hint")
{
if (hitcounter < 10)
{
//preveintg double hint. something like that.
//you can use later array or list if you need more hint
int hint = generaterandomhints();
while (hint == lastHint)
{
hint = generaterandomhints();
}
hitcounter++;
//write the hints
}
else
{
//write you reached the maximum of the hints
}
}
}