Я немного изменил вас, Regex, и я могу сопоставить обе строки. У меня есть регулярное выражение:
/On.* \d{1,2}\/\d{1,2}\/\d{1,4}(?:, at)? \d{1,2}:\d{1,2} (?:AM|PM),.*wrote:/
Сравнение результатов двух:
irb(main):023:0> s1 = "On 25/03/2011, at 2:19 AM, XXXXX XXXXXXXX wrote:"
=> "On 25/03/2011, at 2:19 AM, XXXXX XXXXXXXX wrote:"
irb(main):024:0> s2 = "On 3/14/11 2:55 PM, XXXXX XXXXXX wrote:"
=> "On 3/14/11 2:55 PM, XXXXX XXXXXX wrote:"
#Your previous Regex
irb(main):025:0> m = /On.* \d{1,2}\/\d{1,2}\/\d{1,4}(, at)? \d{1,2}:\d{1,2}(?:AM|PM),.*wrote:/
=> /On.* \d{1,2}\/\d{1,2}\/\d{1,4}(?:, at) \d{1,2}:\d{1,2} (?:AM|PM),.*wrote:/
irb(main):026:0> s1.match(m)
=> #<MatchData "On 25/03/2011, at 2:19 AM, XXXXX XXXXXXXX wrote">
irb(main):027:0> s2.match(m)
=> nil
#The updated Regex
irb(main):028:0> m = /On.* \d{1,2}\/\d{1,2}\/\d{1,4}(?:, at)? \d{1,2}:\d{1,2} (?:AM|PM),.*wrote/
=> /On.* \d{1,2}\/\d{1,2}\/\d{1,4}(?:, at)? \d{1,2}:\d{1,2} (?:AM|PM),.*wrote/
irb(main):029:0> s1.match(m)
=> #<MatchData "On 25/03/2011, at 2:19 AM, XXXXX XXXXXXXX wrote">
irb(main):030:0> s2.match(m)
=> #<MatchData "On 3/14/11 2:55 PM, XXXXX XXXXXX wrote">