Elena Gilbert: You've lived in Mystic Falls for most of your life, and have known Elena for much of that time. You were both still kids when you met at school, but you left a lasting impression on each other.

 Bonnie Bennett: You were a friend of Stefan Salvatore and Lexi Branson who came to town with them. You met Bonnie through them, since she was Elena Gilbert's best friend. You instantly take a liking to her, and she seems to like you, too.

 Caroline Forbes: You've known her your entire life. You're Tyler's brother/sister, and you envied him for snagging a girl as great as her.

 Katherine Pierce: You met centuries ago, when Katherine was still human. You were a friend of the Mikaelsons, and met her when Elijah introduced you. Though she was more interested in Elijah at the time, you always liked each other.

 Jenna Sommers: You knew each other in high school, but didn't see each other again until Jenna came back to Mystic Falls after her sister's death to take care of Elena and Jeremy. You were both surprised to run into each other on the sidewalk, and you were impressed with the way she did what she could for her niece and nephew.

 Vicki Donovan: You meet when you go to the Mystic Grill one evening for a drink. You sit at the bar, she behind the counter, and the two of you start chatting, and find you have some things in common. You exchange phone numbers and agree to meet again sometime.