What types of relationships does Holden attempt to create throughout the novel The Catcher in the Rye?

Holden vacillates between wanting relationships and
rejecting them, in a fashion perhaps that is a caricature of typical adolescent
behavior.  Holden does talk several times about being "alone" in the novel, and not
liking it, but then he does things which specifically create loneliness for himself. 
Holden has the desire to denigrate everything around him (calling people "phonies" for
example), while at the same time wishing to be part of something and have relationships
with other people.

One example would be the relationship
(or encounter) that Holden attempts to have with the prostitute Sunny.  Holden thought
that perhaps he would have his first sexual experience with her, but that does not
happen.  He tries to talk to her about his feelings, and make a friendly connection with
her, but she is not interested in talking to Holden.  She ends up cheating him and her
pimp demands double the fee that was originally agreed upon.  Holden fails utterly
to make any connection with Sunny.

Though Holden says a lot
of bad things about Sally Hayes, he tries to make a connection of a romantic kind with
her.  Though they neck in the cab, the fact that she enjoys things that he doesn't (like
the play they go to see, and the movies) alienates him from her.  He asks her to run
away with him, which of course she refuses.  Again, Holden fails to make any kind of
real connection with Sally, and succeeds only in making her angry and
frightened.

Holden wants, and achieves, a close
relationship with his sister Phoebe.  It is plain from the novel that Phoebe has always
been close to him, perhaps even more now after the death of their brother, Allie. 
Holden spends time in New York before seeing his sister, but he thinks about her often
and eventually makes goes home specifically to see her.   He reaches out to her and
tells her how distressed he is by telling her that he is going to run away.  Phoebe
responds loyally and lovingly, if misguidedly.  Phoebe and Holden's relationship is
continuous and successful. 

Holden does want some kind of
relationship with his overbearing roommate Stradlater, but it does not end up how he
wants it to be.  Stradlater dates a girl who Holden knows, which angers Holden. 
Stradlater uses Holden to do his homework for him, and then criticizes the paper Holden
writes for him.  Stradlater ends up by beating Holden up.  Any constructive relationship
is lost between the two boys, mostly because of their own problems with each other and
character failings.

Holden says he doesn't want to have a
friendship with the annoying hallmate at Pencey Ackley.  But Holden is very lonely, and
tries to alleviate this loneliness by hanging out in Ackley's room even after Ackley is
asleep.  This is more a relationship desired out of desperation; Holden doesn't really
like Ackley.

Holden wants a kind of mentor/fatherly type of
relationship with Mr. Antolini, which succeeds for part of the evening.  When Mr.
Antolini touches Holden (stroking his hair), however, Holden is convinced (possibly
correctly) that Mr. Antolini has homosexual desires for him.  This creates such a
problem for Holden that any further relationship with his ex-teacher is
ruined.

Holden attempts to have relationships of the
sexual, romantic, friendly, mentor, and familial kind, with varying
success.