Bobby first laid eyes on Tiffany at a Trail Monkey's Jeep event, a event where Tiffany was going to see his friend. Later, Tiffany popped up on Bobby's suggested friends list on Facebook so he decided to start "poking" her. After a few pokes back and forth, Tiffany finally messaged Bobby telling him "Listen buddy, I don't know who you are but you will not win this poke war!" From there Bobby managed to get Tiffany phone number and the rest is history