Advice: On interacting with someone on the rebound

A guy asked for my advice recently. A girl that he is
interested in just recently broke up with her boyfriend
of two years, and said she isn't interested in dating
anyone. He asked me what he should do.

My first comment to him was a question:
What do you want?

He didn't know.

I explained to him that it had to start there. He then
said that he just wanted to "hang out" with her.

I said that if he just wanted to "hang out" then he could
potentially tell her, "I know you just broke up with
someone, and I think you're cool. I'd like to just hang
out with you, if that would be OK." If he really wanted
to be brave, he could add, "Make no mistake, I am
attracted to you, and I respect where you are right
now, and should you change your mind we can talk
about it."

I told him that if he said those words he'd have to mean
all of them, otherwise she might see through him, and
he might wind up frustrated or disappointed. I also told
him that If he said those words, and meant them, he'd
also be OK with whatever her response was, even if she
wasn't interested.

He asked what the difference between just hanging out
and dating was. I said there may be no difference, that
each person's idea may vary. However he needed to
be honest with himself if he felt they were one in the
same, as the knowledge that she said she isn't interested
in dating right now tells him that they're in different
places. That alone is an answer.

Someone who is just coming out of a relationship is
going to be reactive. Many times you'll hear people say
that rebound relationships don't work out. You also run
the risk that the person could get back with their previous
partner. I once tried to end a relationship twice, before it
finally ended on the third attempt.

The dance of relationships is never easy, and it is made
more complicated when people aren't honest with themselves,
and/or they come with expectations that may or may not be
met. Even in the healthiest and best of situations, there is
a tendency to have expectations and often the one who
has them can wind up disappointed.

Some would say to stay away from a situation like this.
However, it all depends on what you want, and how you
walk into it. The relationship that I tried to get out of three
times was one that going into it I had questions. However
I felt at the time that what I was about to do was something
I felt I needed to do. If I didn't, I'd always wonder, "what if..."
So I made myself a promise that no matter what happened,
I would be OK with it and, in the end, I was.

He could also walk into it clear that he is OK with "just
hanging out," and find that he develops feelings for her in
the process that aren't reciprocated. He needs to realize
that this is a possibility, and he needs to take responsibility
for his experience, and be OK with whatever outcome results,
even one that he doesn't want.

Problems come when people aren't clear. I wish I could say
clarity negates disappointment, but unfortunately, things
don't always work out the way we want them to. Each person
needs to decide for themselves what is an acceptable course of
action, and it needs to start with an honest assessment of oneself
and the situation.

The beauty of life is that you just never know what can happen,
and if you listen to what others tell you, you may miss out on
pain and disappointment, and you also may miss out on
something pretty special.

No one ever said life was easy, or would be without pain, and to
avoid the possibilities of those things is sometimes to avoid the
possibility of some of life's greatest pleasures.

In the end, the value of anything is the worth you assign to it.
There may be more value for you in avoiding the pain than there
is in the possible pleasure. I wish I knew THE answer to give this
guy, or anyone, but I don't have it. Only he knows what the best
thing to do for him is, and it starts with asking the right questions.