Jabes.plays.RPG says:
Bobby went on to become a chef of some small renown but part of him feels like his entire life in this world is just a dream or a pale reflection of the one in the Realm. He's in a committed relationship with Terri, who has some appreciation for his attachment to his life in the Realm, although she has no desire to go back, and (Bobby suspects) only tolerates his need to adventure out of love for him.
Every part of that is me getting autobiographical. I realize if I put any more nuance to it, drawing from my own struggles with mental health and anger issues, this will get pretty grimdark. I think that would be neither healthy nor a good contribution to this game. So I'll leave it vague like that. And with that as a starting point for relationships:
Sheila: Bobby became much closer with Sheila as they grew up, and have supported each other through all of their individual struggles.
Eric: Bobby has had little contact with Eric. Most of what he knows, he heard through Hank.
Presto: For Boby, visiting Presto in the Realm is always a breath of fresh air. Even if it means, as it has countless times, having to face some unspeakable evil together. Presto is the only one besides Sheila and Terri that Bobby has confided in about feeling lost in the real world.
Diana: Despite his obvious athleticism, Bobby never got into sports, and has never felt comfortable around athletes. Still, he has followed Diana's gymnastics and MMA careers on the news enthusiasm.
Hank: As long as Hank lays off the guidance counselor crap, Bobby always looks forward his calls and visits. Even though it often makes him melancholy, he enjoys hearing those little tidbits about the others that Hank likes to share. Once, Bobby started to open up to Hank about feeling more attached to the Realm than their own world. What was Hank's response, @BedzoneII?