HERE IS THE NEXT CLUE:
1) Riley's Secret Buddy weighs the same
OR Less than him...
2) Riley's Secret Buddy Lives In A State That Is Larger
Than His State [Washington, DC] ...
3) Riley's Secret Buddy's State has less letters than Riley's State [
District of Columbia]...

4) This is "NOT" Riley's Secret Buddy's first Gift Exchange...
5) Riley's Secret Buddy Is A Veeeeery Pretty Girl
6) Riley's Secret Buddy Lives to the South of him!!
7) Riley's Secret Buddy Shares at least one letter in their names...