Here's a better fit version...

Code:
Dim l As New List(Of String)(New String() {"* This is a short one.", _
                                                    "* Another short one.", _
                                                    "* This is a very long one", _
                                                    "spanning a whopping", _
                                                    "three lines.", _
                                                    "* Still another.", _
                                                    "* Yet another.", _
                                                    "* Back to a short one.", _
                                                    "* And another short one.", _
                                                    "* Last one here."})
Dim count As Integer = l.Where(Function(sentence) sentence.StartsWith("*")).Count
Dim f As Integer = count \ 2
Do
    If (l(f).StartsWith("*") And l(f + 1).StartsWith("*")) Then
        Exit Do
    Else
        If l(f).EndsWith(".") Then
            Exit Do
        Else
            If l(f + 1).EndsWith(".") Then
                f += 1
                Exit Do
            Else
                f += 1
            End If
        End If
    End If
    If f = l.Count Then Exit Do
Loop
Dim firstList As List(Of String) = l.Take(f + 1).ToList
Dim secondList As List(Of String) = l.Skip(f + 1).ToList