Why does a "do until" loop stop the subroutine?

Hello,
Any idea why the first loop stops the sub, it doesn't proceed to the second loop..

    Do Until IsDate(EnteringDay) = True
        EnteringDay = InputBox(prompt:="What's the date? Enter in this format 01/01/2015", _
        Title:="Weight Watchers", Default:=Format(Now(), "dd/mm/yyyy"))
            If IsDate(EnteringDay) = False Then _
                EnteringDay = InputBox(prompt:="What's the date? Enter in this format 01/01/2015", _
                Title:="Weight Watchers", Default:=Format(Now(), "dd/mm/yyyy"))
    Loop
       
    Do Until IsNumeric(EnteringWeight) = True
        EnteringWeight = InputBox(prompt:="What's your weight? Enter in this format 75.00", _
        Title:="Weight Watchers", Default:="75.00")
            If IsNumeric(EnteringWeight) = False Then _
                EnteringWeight = InputBox(prompt:="What's your weight? Enter in this format 90.00", _
                Title:="Weight Watchers", Default:="90.00")
    Loop

It is not proceeding because you are asking for a string, and keeping it a string.

But also, you will always have problems with ambiguous dates - VBA is US-Centric for dates, so 5/7/2015 will be May, not July.

So try

    While Not IsDate(EnteringDay)
        EnteringDay = CDate(InputBox(prompt:="What's the date? Enter in this format: Nov 12, 2015"))
    Wend
        
    EnteringWeight = Application.InputBox(prompt:="What's your weight? Enter in this format 75.00", _
        Title:="Weight Watchers", Default:="75.00", Type:=1)

    MsgBox EnteringDay & " " & EnteringWeight

Better would be to use a calendar control - here's a workbook with an example that will work:

Simple Calendar.xlsm

@Bernie, Thx for your help! I'll use your method for the weight question also. But how do I verify that the user enters a valid date. Right now running your code, if I enter no date at all (into the input box) the code just stops.. the do until loop was intended originally to force the user to enter a correct value into the inputbox..

You need to handle that error:

    On Error GoTo ErrHandler
getDate:
    While Not IsDate(EnteringDay)
        EnteringDay = CDate(InputBox(prompt:="What's the date? Enter in this format: Nov 12, 2015"))
    Wend
    
    EnteringWeight = Application.InputBox(prompt:="What's your weight? Enter in this format 75.00", _
    Title:="Weight Watchers", Default:="75.00", Type:=1)
    
    MsgBox EnteringDay & " " & EnteringWeight
    
    Exit Sub
ErrHandler:
    Resume getDate

@Kyle - I'm trying to refrain from form in this specific case. Thanks anyway.
@Bernie - It works just fine! and i'll also seize the opportunity to learn more about "ErrHandler"..