This is my take on your question. For ease I'm using a checkbox array instead of individual controls.

Code:
Private Sub cboDays_Click()
Dim dteTemp As Date
Dim intMonth As Integer
Dim intYear As Integer
Dim i As Integer
    'find the first selected day of the month
    intMonth = Month(Date)
    intYear = Year(Date)
    dteTemp = DateSerial(intYear, intMonth, 1)
    
    Do While Format(dteTemp, "dddd") <> cboDays.Text
        dteTemp = DateAdd("d", 1, dteTemp)
    Loop
    
    ' Add tooltips to the checkboxes
    For i = 1 To 5
        chkWeek(i - 1).ToolTipText = DateAdd("ww", i - 1, dteTemp)
    Next i
End Sub

Private Sub Form_Load()
Dim i As Integer

    cboDays.AddItem "Sunday"
    cboDays.AddItem "Monday"
    cboDays.AddItem "Tuesday"
    cboDays.AddItem "Wednesday"
    cboDays.AddItem "Thursday"
    cboDays.AddItem "Friday"
    cboDays.AddItem "Saturday"
    
    For i = 1 To 5
        chkWeek(i - 1).Caption = "Week " & i
    Next i
End Sub