What to do about a recently divorced boss who’s dating a crazy woman?

Because no one asks me any questions here I recently signed up to be an "expert" on divorce and relationships on a web site full of people who love to answer questions located at http://www.allexperts.com/. I know, I know, I have to much time on my hands, but lo and behold within one day I received the following question from Lisa who lives in Somewhere, USA:

Question: One of our customers, I might as well call him a boss, was divorced about a year ago and has a 15 year old daughter.  He moved in a few months after leaving his wife with some bimbo who has kids from different fathers and is also recently divorced.  I’ve always had issues with women who jump into a relationship and have men move in or they move in with men when they have kids.  I’ve seen it often and it is generally a bad experience.  Our boss wants us to go out to dinner, etc with the new girlfriend who he lives with.  I’m not too impressed by her at all.  She seems like a jerk and I don’t have much respect for her.  While our boss is wonderful and has been great to us, to the point we consider him a friend, I have a hard time pretending to like someone who I think is a tramp.  I realize he can be looked down upon by moving in so quick with a woman like this, but it was a bad divorce where he lost a lot.  This girl is 20 years younger than him and I think she’s playing him.  So another issue, I think she’s a user!!  He seems like a HS kid who is in love for the first time.  I really don’t want to go out even one night.  Am I wrong to feel this way?  What should I do?

Answer: Hi Lisa — thanks for writing. I just signed up to be an expert and yours is my first question.

OK … so, when faced with any obstacle a person has three choices. The choices are:

1. Accept.
2. Change.
3. Eliminate.

In this case this means you could accept the situation the way that it is. Let me help you with this one…

Know that divorce triggers all sorts of primal fears — the fear of abandonment, rejection, and there are attachment issues playing a role as well. Breaking an attachment to someone you’ve been with a while is always extremely stressful, even when you know the break up is for the best. The combination of these issues (and more) mean that a person who goes through a divorce will be "off center" for about two years or so. In fact, I tell my clients to forgive the behavior of their divorcing friends and family during this time for they know not what they do, and i call it being temporarily insane, because basically that’s what it is. (Forgive so long as the behavior is not illegal!) This crazy time is when divorcing men and women do things out of character … like buy a motorcycle, get a tattoo, and yes, take on unexplainable partners — sometimes doing this is a rebellion against conformity, as they are telling themselves that they have fit themselves into society’s box for years, and now it is time to conform to nothing! As a result I have seen wealthy doctors date pizza deliver boys, housewives in gated communities date the yard man, and on and on … but basically, how it goes is that anything goes. Don’t worry, though, there is nothing you can do about this and almost everyone wakes up from this coma of craziness after about two years. With my own friends I usually go with the flow of whatever comes … knowing that they will almost certainly come back to their senses sooner or later.

Now, about No. 2, change. The change part means you can tell your friend to change, or you can change the way you view the situation. As far as asking the friend to change, I think it is arrogant to tell people that you know better than they do, so I don’t recommend this option. What you can do is approach it in a gentle manner ONE TIME as a caring and loving friend and tell your buddy that you are concerned about his relationship. If you do this, have no expectations as to what the outcome is. Just lovingly tell him and know that you did the best you could and that you were well-meaning. As far as changing how you view it, maybe you  can tell yourself that he is going through a change and is supposed to be learning something. Lovingly allow him to learn what he is supposed to be learning.

Eliminate is the last and most drastic option. If you can’t accept or change, then you eliminate. Eliminate what, you ask? The friendship … or if he is like a boss and you can’t totally break away, you can consider distancing yourself as a social friend, and just enjoy him at work.

One last thing. I’m not a huge fan of being judgmental. I see people who most of us might see as "messed up" as people who are emotionally wounded. Heaven forbid that we learn all the ways and reasons this person has been injured, neglected, and hurt in her life – it is probably too horrible a thing to even consider. Any of us could have been subjected to such unspeakable cruelty. Therefore, I can find compassion for the emotionally wounded, and if they allow me, I can be tender and caring toward them. Have you thought of doing that with this woman?

Good luck to you and I thank you for sending in this question.

So Struggle readers, what do YOU think, did I blow it?