In general, Jess's family does not have a big problem with Jess being friends with Leslie. That does not mean they are all completely supportive of Jess, though. Jess's dad is probably the least supportive of the friendship. He has some fairly archaic ideas about how boys and girls should associate. He also doesn't like how Leslie tends to pull his only son away from doing "manly" things. Brenda and Ellie don't seem to have a problem with Jess and Leslie being friends, either. They tease Jess a lot about it, but I don't believe that means they are against the friendship. I would say that they like that Jess and Leslie hang out together because it gives Brenda and Ellie the opportunity to tease Jess more. May Belle is the most positive about the friendship between Jess and Leslie. That's why she is always trying to tag along and find out what they do together in the woods.