The .NET DateTimetype has a whole set of parsing methods, including some that allow you to specify a pattern or several patterns, specifying the desired format. Having guessed a little about the format , you have:
$culture = Get-Culture
$format = "M'/'d'/'yyyy h':'mm':'ss tt"
$date1 = [DateTime]::ParseExact('6/16/2014 3:52:48 PM', $format, $culture)
$date2 = [DateTime]::ParseExact('6/16/2014 4:05:53 PM', $format, $culture)
DateTime , TimeSpan, PowerShell V3 , , .NET 4, ( "standard" "custom" , ), :
$between = $date2 - $date1
$between.ToString("hh':'mm':'ss")
$between
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