|Diana and Grant|
Grant and Diana first met in the episode Lucky when Grant seems to have an interest on Diana and started to talk with her and Melissa. Grant later came to Casino night and give out hundred dollars bills where Diana was sitting, counting chips and Diana commented him by telling that is a lot of chips.</p> He later came back and asked Diana how many tickets does he need to get the monkey stuff animals.Diana said 50 tickets then Grant bought two of them, one for him and one for Diana. Later on when he was walking with Diana to her car (Diana is wearing his coat) they talked for awhile and kissed, Grant and Diana went ice-skating then Diana went to see him and discover he doesn't own a boat and that he is traveling with a crew. Grant tried to make Diana understand that he did it to impress her, but Diana was so mad so she walked away from him. He later asked her to give him a chance which she did.
In Crystal, Grant invited Diana on to the boat as a date and say that his captain allowed him to get the boat for a day. But it didn't turn out great when the circle kept needing Diana's help, this make Grant very suspicous and he asked for an explanation. She then promise him she will give him one day to explain, but Grant is unsure if he will return to Chance Harbor.
In the episode Prom, Diana and Cassie go to the coffee house where Diana runs into Grant. He explains how he is docked in Chance Harbor for a little while, Diana invites him over to her house after she gets back from the Prom at her school. Later in the episode Diana finds out that her father, Charles killed Cassie's mother, Amelia. Diana runs outside crying when Grant shows up in his car, he comforts her and tries to calm her down.
In Family, Diana finally decides to run away from Chance Harbor with Grant, as he had always joked about taking her across the country.