poor girl, she sounds really insecure like she has something to prove
My oppinion-- he still is madly in love with jessica and jessica is totally OVER him. In about 18-36mts he will totally get over jessica and enjoy being with other women, he may even reason that being with jessica was 'Puppy love' and insignificant. In the mean time, Jessica will realize that that not ALL men are just dying to be loving and caring and faithful and supportive, and that she let something very special go. Shell want him back, and hell be long gone.
I promise