using System;
using System.Collections.Generic;
using System.IO;
using System.Linq;
using System.Text.RegularExpressions;
 
public class Test
{
	public static void Main()
	{
		var s = "Request closed by Jack Arm on 08/16/2018,Assignee #1 James Arye assigned by Scotty Shep on 08/16/2018,Request submitted by Mac Weaver on 08/16/2018,Request created by Mac Weaver on 08/16/2018";
    	var pattern = @"((?:[a-zA-Z'-]+[^a-zA-Z'-]+){0,2})assigned by((?:[^a-zA-Z'-]+[a-zA-Z'-]+){0,2})";
    	var matches = Regex.Matches(s, pattern);
        foreach (Match match in matches)
		{
        	Console.WriteLine(match.Groups[1].Value.Trim());
        	Console.WriteLine(match.Groups[2].Value.Trim());
		}
	}
}

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