Barbara Hinkley is a woman Jack Schafer casually dated in book #77 Dawn and Whitney, Friends Forever . Jeff and Dawn went along with the couple on a family date to Cap'n Frank's Fun Fish Fry . Jack met Barbara at the dentist. Barbara seems to be an independent person who preferred to meet the Schafer family at the restaurant rather than go with them. She wore an expensive tailored suit to the date and looked down on everyone, including the Schafer family. She seems to also be very health conscious as she was very precise and picky about what she ordered.