public void Form1_Load(Object sender, EventArgs e) 
{
    ... // Other initialization code
    maskedTextBox1.Mask = "00/00/0000";
    maskedTextBox1.MaskInputRejected += new MaskInputRejectedEventHandler(maskedTextBox1_MaskInputRejected)
}

void maskedTextBox1_MaskInputRejected(object sender, MaskInputRejectedEventArgs e)
{
    toolTip1.ToolTipTitle = "Invalid Input";
    toolTip1.Show("We're sorry, but only digits (0-9) are allowed in dates.", maskedTextBox1, maskedTextBox1.Location, 5000);
}

Private Sub Form1_Load(ByVal sender As System.Object, ByVal e As System.EventArgs) Handles MyBase.Load
    Me.ToolTip1.IsBalloon = True
    Me.MaskedTextBox1.Mask = "00/00/0000"
End Sub

Private Sub MaskedTextBox1_MaskInputRejected(sender as Object, e as MaskInputRejectedEventArgs) Handles MaskedTextBox1.MaskInputRejected
    ToolTip1.ToolTipTitle = "Invalid Input"
    ToolTip1.Show("We're sorry, but only digits (0-9) are allowed in dates.", MaskedTextBox1, 5000)
End Sub

private void Form1_Load(Object sender, EventArgs e)
{
    // Other code
    maskedTextBox1.ValidatingType = typeof(System.DateTime);
    maskedTextBox1.TypeValidationCompleted += new TypeValidationEventHandler(maskedTextBox1_TypeValidationCompleted);
}

Private Sub Form1_Load(sender as Object, e as EventArgs)
    // Other code
    MaskedTextBox1.ValidatingType = GetType(System.DateTime)
End Sub

public void maskedTextBox1_TypeValidationCompleted(object sender, TypeValidationEventArgs e)
{
    if (!e.IsValidInput)
    {
       toolTip1.ToolTipTitle = "Invalid Date Value";
       toolTip1.Show("We're sorry, but the value you entered is not a valid date. Please change the value.", maskedTextBox1, 5000);
       e.Cancel = true;
    }
}

Public Sub MaskedTextBox1_TypeValidationCompleted(sender as Object, e as TypeValidationEventArgs)
    If Not e.IsValidInput Then
       ToolTip1.ToolTipTitle = "Invalid Date Value"
       ToolTip1.Show("We're sorry, but the value you entered is not a valid date. Please change the value.", maskedTextBox1, 5000)
       e.Cancel = True
    End If
End Sub