It's hard to describe how Bailey would feel about the others. I've been racking my brain for a while and I think the best way I can describe it is that Bailey is very socially inept and lacks the proper empathy to really relate to others who are not invested in the same things that interest him. For that reason, Bailey and Lucille will probably get along due to them both liking video games. Though he will most likely be that one annoying friend who does nothing but talk about games.

On the other side of the coin, he's also quite self conscious and has a desire to be liked and understood even though he's not so great at the latter himself. As a result he comes off as someone who really tries too hard to make friends, but just says all the wrong things. He gets hung up on what he says easily and spends a lot of time worrying about how his words are perceived.

He basically thinks that he needs to continually prove himself to be worthy of the others friendship. How this is received by the others is dependent on their own respective personalities.

As for specific characters;

Bailey likes Lucille. She's nice and likes video games. Enough said. Her appearance took a bit of getting used to though.

Bailey sees Ken as a standard to hold himself to. Ken is a cool, pretty level headed guy who is also very physically able. Perhaps there's potential for a rivalry here?

Marlin is a freakin' wizard. Bailey thinks that's the coolest thing ever. Marlin is also pretty chill, but Bailey still keeps a distance for now.

Lilith scares Bailey. In her heroic persona, Bailey is terrified of her. Even her regular old nice self feels a little too unapproachable to him. Not to say it's because Lilith is like that, but rather Bailey doesn't see himself as someone she should waste her time on.