Dear Ms Know it all,

I have a very dear girlfriend of 13 years. She is my soul sister and I adore her. Unfortunately, for the past three years, she has been totally obsessed with gaining the affections of a guy she works with (note that I didn’t call him a “man” but a “guy”) who I feel is unworthy of all the time and effort she has invested in him. They are work friends who hang out outside of work, mainly happy hour type social stuff in groups, but he is a 40-something cad who prefers much younger women. To his credit and the discredit of young women everywhere, he is very successful in bagging the young babes because I guess they find him attractive – I just don’t see it! Anyway, what can I do to help my friend move on? I’ve tried being brutally honest but she deflects and justifies and denies and then falls into the same old patterns of obsessing over what every nuance with him means. It’s really an unhealthy waste of time how doing this has become her hobby, almost. I mean, I just think he isn’t interested and it would have happened by now if it was going to happen. IT’S BEEN THREE YEARS. I’ve tried coaching and being supportive but frankly, I’m sick of hearing about the guy! HELP. 

-Austin L

Dear Austin L,

Hia! Awwww….love you so much and of course you have put up with her (at this point, there is no other word) pitiful self because that’s the kind of friend that you are and that’s the very definition of a good friend. Saddest part of all of this is that there is absolutely nothing which you can do, my love.

The bottom line here is that she sounds a little obsessed with this guy and a part of her must absolutely get off on him not actually wanting her — because if he did, he would have already engaged. There’s nothing about this that smells good except perhaps your intention to try and help your friend.

I know that you don’t want for her to go through this alone. I also know that you don’t want for her to feel alienated. But knowing you, which I do, you have likely approached this from every single possible angle available to you, running the spectrum from compassion to  brutality. After 3 years, it’s time for you to tap out. Here’s the confusion about being a friend; people think that to be a good friend, you have to always be there for the other person, but sometimes the best thing a friend can do is to no longer engage a particular subject matter. Essentially, it’s knowing where to draw the line so that you are not enabling destructive behavior.

Consider the following — if she were cutting herself with a knife, you wouldn’t hand her the knife would you? This is the same thing, except the cutting is emotional, soul and heart-directed.

After 3 years, I will say (very gently) to you that at this point, any room which you give her to talk about this subject is in fact room that you give her to think, engage, dissect, consider as a viable option, a seemingly very very bad decision on her part to continue to pursue a thing which is not available. To continue this conversation is to keep helping her cut herself.

Reality is that no matter how much we would like to, we can’t make anyone we love be healthy. We can’t make them choose better, or behave healthy, or engage only goodness. All we can do is be there quietly and steadily and help them when the time is right. You have said your piece repeatedly and in different ways. Now, you have to have an extremely difficult conversation and say clearly that this topic about this guy is off the table. That you love her deeply and because you love her, you have given her as much as you can, and you will no longer enable her own emotional self-cutting. Should she one day choose to extract herself, then you will step back in and help her in every and any way that you can.

To our own heart-ache and completely beyond our control, we must often allow our loved ones to be the architects of their own demise. Sometimes, it’s only when people shatter at rock-bottom that they can rebuild cleanly and in healthy manner. After three years, it is her choice to do so and your only role at this point is to sit back and let her engage in this destruction as she has clearly chosen to make this her only path. It will be painful for you to do so, but this is the only thing which you can do in order to help her right now, and then…be there for her when she crashes and burns (which she will). Help her pick up the pieces and love her at that point as ferociously as you do right now.

Pray it doesn’t take her another wasted 3 years to get to her rock-bottom.

Keep me posted, please.

All my love,

M