Hi! I have a kind of survey question that I'd love you to answer if you can.
With which 2 characters did Gilligan have his 2 most significant relationships
on the island--and how would you label each of these relationships? Thanks!

Well there's the Skipper of course, who was Gilligan's boss and also his roommate, confidant, father-figure, etc. This was sort of a love/hate relationship, as they got on each other's nerves frequently (e.g. Skipper calls Gilligan stupid, Gilligan calls Skipper fat).

The other one is either Mr. Howell or Ginger. I say Mr. Howell because there were episodes where he was more "fatherly" to Gilligan while the Skipper was more "bossy". Mr. H always called Gilligan "my boy" which I thought was kind of sweet and showed that deep down inside Mr. H did love and care about Gilligan, even though he got exasperated and made jokes at Gilligan's expense at times.

So why did pick Ginger too? I notice that Gilligan and Ginger had quite a lot of scenes together (fishing, hunting for seashells, etc.) and it seems like they were just really good friends, with Gilligan being intimidated yet at the same time facinated by her. Also, Ginger was kind of flakey and Gilligan was also kind of flakey (e.g. believing in magic, tarot [see "Ship Ahoax"]). Gilligan also has seen a lot of movies and believes that what goes on is real! :) So here was someone closer to his own age to "play" with, so to speak. As far as Mary Ann goes, seriously there aren't really all that many scenes I can remember that have Gilligan and Mary Ann alone together. The ones I can think of usually have Mary Ann rolling her eyes at Gilligan in the end. So I wouldn't put her as #2, even if Gilligan liked her cooking. Mrs. Howell was a motherly figure to him and I think that Gilligan just couldn't relate to the Professor very well.

So, really Gilligan considered himself to be friends with everyone on the island.

But didnt mary ann make a comment in 1 of the 1st episodes telling gilligan that she thought he was so sweet and gave him that I got a crush smile?

There were a few early episodes where Mary Ann indicated an attraction to Gilligan. For example:

1) Voodoo Something to Me - Gilligan describes how he "fought" off the "monster" in the supply hut and Mary Ann squeals "Isn't he wonderful!"

2) President Gilligan - Mary Ann inexplicably votes Gilligan for president saying "Gilligan is my man too!"

3) Goodbye Island - Gilligan and Mary Ann are extracting sap out of trees and Mary Ann says the sap is sweet "Just like you Gilligan".

I think that after the "Matchmaker" episode Mary Ann seemed to lose interest in Gilligan in that kind of way, although there was a scene in "Hair Today, Gone Tomorrow" (that must have been edited out on TV because I'd never seen it before I saw it on DVD) where Mary Ann (not Ginger, there's a switch) is trying to snap Gilligan out of thinking he's old by telling him she loves him and then kissing him.

There were a few early episodes where Mary Ann indicated an attraction to Gilligan. For example:

1) Voodoo Something to Me - Gilligan describes how he "fought" off the "monster" in the supply hut and Mary Ann squeals "Isn't he wonderful!"

2) President Gilligan - Mary Ann inexplicably votes Gilligan for president saying "Gilligan is my man too!"

3) Goodbye Island - Gilligan and Mary Ann are extracting sap out of trees and Mary Ann says the sap is sweet "Just like you Gilligan".

I think that after the "Matchmaker" episode Mary Ann seemed to lose interest in Gilligan in that kind of way, although there was a scene in "Hair Today, Gone Tomorrow" (that must have been edited out on TV because I'd never seen it before I saw it on DVD) where Mary Ann (not Ginger, there's a switch) is trying to snap Gilligan out of thinking he's old by telling him she loves him and then kissing him.Given the time and what they could or could not show maybe the decided to water Mary Ann's feelings for Gilligan down,it would be easier to imagine them as a couple than Gilligan and Ginger maybe the writers and producers decided to scrap that side of the Mary Ann/Gilligan relationship.I also think maybe she had a crush on in and in time it just faded away like most crushes do.
The Skipper was Gilligan's most important relationship,it was sort of uncle/nephew like of course Gilligan worked under him but clearly they were much more that just skipper and first mate to each other.
Second is difficult but probably Ginger,it seemed to be the safer way to go(no one could see them romantically) and they played off each other very well better than he did with Mary Ann I think.Ginger and Gilligan were a sort of brother/sister duo.