How Long To Wait?

I'm not a relationship expert.  I've never even taken a psychology class.  However, it seems to me that my friends usually come to me for relationship advice, and they all agree I'm probably right.  Why don't they take it?

I'll call my friend Jane for the sake of this blog.  Jane is 26 years old, and spent ten years with the same guy, John.  Her high school sweetheart, they planned to get married and have kids someday.  But someday was not soon enough for her, and it was too soon for him.  John has had many, many problems in the past five years.  Unfortunately, one of them includes drug use.  It hasn't been occasional, either.  Jane does not endorse drug use and asked him to stop or she would leave him five years ago.  He quit.

Until about four months ago, they were doing fine.  Suddenly, though, John began to forget to do things.  They lost their place together, and he had to move back in with his parents.  Jane wasn't sure what to do, so she gave him an ultimatum: it's me, or the drugs.

John chose the drugs.  That was two months ago.  Jane has been a wreck since then, and every time she seems to be doing okay, he seems to call or text message her, and she becomes an emotional wreck again.  This is not the topic, though.

How long should she wait before getting back into the dating scene?  Well, my answer to her was, "Dude, seriously, you've been in a relationship with the same guy for ten years.  You never even explored your options or had a chance to have fun.  I think you need a break." 

This lasted a week.  First, she hooked up with my boyfriend's brother for a short time, because they were both going through a hard time.  I understood that.  They connected and that is fine with me.  I knew it wouldn't last, and it didn't.  Thankfully.  Just a couple weeks later though, she started hanging out with a co-worker (whom also works with my boyfriend).  They basically are together all the time.  Every weekend we all get together and we have drinks and have fun.  We go bowling and barbeque and play cards and really, it's great to have another couple we get along with to hang out with.

The problem is this: this past weekend, Jane got a text message from John, telling her he misses her and hopes she is doing okay.  I wouldn't have said this was a problem.  However, the guy she is hanging out with (Joe, for the sake of this blog) was with us.  We were watching a movie and she gets this text, and suddenly Chris and Joe get up to go to the store. 

Jane bursts out in tears and says she doesn't know what John wants from her.  Why is he doing this?  Doesn't he know how much it hurts?

I can understand her pain; what I don't understand is why she is trying to distract herself from getting over him by using Joe.  She says they are in agreement that this is just hanging out for now and it's not serious, but Joe did say he'd like to settle down soon. 

It seems to me in this situation Jane needs to stand back and take things slower.  I haven't seen her without Joe for over a month now.  As far as I'm concerned, this is a relationship without the title, and Joe is playing along with it so she doesn't feel uncomfortable. 

How long should you wait to start seriously dating again?  How long should you give yourself before you jump back in the game?  I'm not sure what the correct answer is to that, really.  I'm not pretending to be an expert.  Since Jane has talked my ear off about this I figured it'd be a good blog.  She claims she is fine with how things are right now.  I say, she is only fine because she is hiding behind Joe.  As long as she is distracted, she doesn't have to deal with her feelings about breaking up with John in the first place.  I can see her, with Joe, in several months, and being happy, but then John coming back into the picture and making her break down because she never settled her feelings over him.

It is a very long and confusing road.  I am young, myself, and have only had one serious relationship before the one I'm in now.  I guess I just knew that I needed time to get over the ex before I tried dating again.  Otherwise, I'd break someone else's heart, and still have a broken heart, myself, and wind up right where I was.  I waited three years before settling down again.  It seemed an appropriate time length for me, because I'm an emotional person.  Jane is even moreso, but can't see that she is going to hurt herself even more.

Sigh.  If only everyone was as logical as I am.  What would you tell your friend if they were asking for your advice?  How long would you recommend waiting?  Or how would you know it was time to move on?