The Love of My Life is in Prison and That’s Just the Beginning

Dear Robin,

My dear sweet boyfriend was just sentenced to 16 years in prison for white collar crime. The case is too complex for me to explain in this letter so I will give you the “Readers Digest” version. I met “Jack” (that’s what I will call him) a little over 3 years ago. We became close friends and always had a fondness for each other. After the collapse of my 13 year marriage, Jack and I became much more than just friends. Jack was a full blown alcoholic during most of the 3 year friendship and the pressure of his upcoming trial fueled his disease big time.

About 7 months ago I got him into rehab. At the time he was drinking about 2 liters of vodka every 24 hours and was nearly dead. I won’t describe this in too much detail but lets just say, not so fresh! Since then we have been inseparable. I loved and supported him through his disease and his trial. He loved and supported me through my horrific divorce as well as the eminent blindness of my 10 year old daughter. (I don’t want to segue into that right now). I am 50 years old and it took me my whole life to find him. He is the kindest person I have ever met. As for his guilt or innocence I will not argue the case but he definitely got a raw deal while others simply walked away.

The appeal is in motion, then a sentence reduction hearing. Blah, Blah,Blah….His first parole hearing is scheduled for 2021. He calls me daily from the jail and he is terrified to say the least. Before he was sentenced I promised him I would wait for him. This was when the lawyers were saying that the he would probably just get one year or parole! I love him and miss him so much. I am consumed with helping him yet terrified this will take me down emotionally and consume my life.

What the hell do I do, and why does this shit always happen to me?

-Born Under a Bad Sign

Dear BUBS (hereinafter “Bubbles,” because that sounds nicer):

Were you under the impression that I was running a contest or something?  I hope I don’t disappoint you when I tell you that you don’t win anything for sending me the most outrageous question ever.


Seriously, ugh.  UGH!  I am so sorry about your troubles.  Readers, Bubbles and I had a long talk yesterday and she is the real deal – I confirmed this with google searches because I am a serious journalist and advice blogger.

The facts of the case brought against her boyfriend do not warrant the sentence he received, so I am hopeful he will get somewhere with his appeal.  Until then and even when he is set free, Bubbles has some serious issues to handle.  Fear not, honey, I’m here to help!

Bubbles’ ten year old daughter suffers from a horrendous disease called “Bardet-Biedl syndrome.”  Those of you with a curious mind can learn more about the condition here:  The rest of you (which I estimate to be about 99% of my audience) should know that the disease causes a host of health issues including blindness, obesity and complications with the heart, liver and digestive system.

How am I supposed to be funny here?  Shit.  Let’s pause for a moment to look at a funny cake, and then I’ll get to my advice for Bubbles.  Here is a photo of a cake they served during harassment training at my last job:*


HR at that company really understood about how to get a message across while still contributing to the obesity of the workforce.  I miss them so.

OK Bubbles, here’s my advice as it relates to your sweetie, which is why you sought my help.  I know you told me you have been looking for this man your whole life, and that he is your best friend and you want to wait for him.  I believe you are deeply in love with him and that if things were different, you could have a nice life together.  However, things aren’t different.


You are 50 years old and going through an extremely contentious and expensive divorce with a man dating a 28-year-old  whose Linkedin profile includes a photo of herself in a bikini.  You have a very sick daughter who will be blind within 5 years.  You are also in the middle of a major home remodel and you are handling your boyfriend’s bankruptcy and divorce while he is in prison for possibly 16 years in another state.


Listen up: when you are ready, you need to start dating other people.  You need to say goodbye, at least for now.  You have so much negative shit in your life right now and maintaining a romantic relationship with a jailbird is going to add to your stress and make personal growth impossible for you.

You told me yesterday that he did not ask you to wait for him, and that when you made the promise to wait everyone assumed the worst case scenario would be a year in prison.  Anyone can wait a year for the right person – you just buy a vibrator and a subscription to Netflix.  But several years?  No.


If he truly loves you, he won’t let you wait for him – he will encourage you to find love with someone who is available both emotionally and physically.  You are still young and very attractive (I stalked your Facebook page – sorry).  On the phone yesterday I was impressed by your wit and your smarts and frankly, I’d like you to be my new best friend.

I know you live in the OC but I’m going to come visit you some day and pour you a drink, because honey, you need one more than most people I know.


But my point is this: you have a lot to offer to a future partner.  If you maintain this connection with your boyfriend, you will be closing yourself off to opportunities to create a new life with a partner who can love and support you fully, especially when you are struggling with some of the problems you cannot control such as your daughter’s health and the fact that your ex is a Douche Bag Supreme who belongs on the cover of Mid-Life Crisis Magazine.


You certainly don’t need to leap into dating now, and in fact I don’t recommend it.  Your divorce is ongoing and nasty and  your boyfriend has only been gone one month.  The last thing you need now is to get on and start weeding through the dickweeds until you find Prince Charming.

But he’s out there, Bubbles.  You deserve to be happy and in love and I fear that your commitment to this man while he is in prison is not good for you in the long run.


Finally, I think it’s important for you to be keenly aware of the impact these circumstances are having on your life.  You told me you are a fairly controlling person, and yet you are saddled with horrible problems over which you can have little to no impact.  For anyone this would be difficult, but for a woman like you (and me) it is nearly impossible to accept that your role in changing the situation and outcome is largely limited.


(hahahahahahahahahahaha, wiping tears of laughter away)


Wouldn’t it be nice if this were true?  But God isn’t going to help you – you need to help yourself.  If you aren’t in counseling already I recommend it.  The right therapist could help you, and for at least an hour once in a while you would get to talk and think about YOU, not everyone else.

And you always have me, Bubbles.  Drive over and visit me in Palm Desert when I am there March 21 – 29.  I’ve rented a lovely home and will have my husband and son with me, plus many friends who will be vacationing there at the same time.  Let’s have a little party and take your mind off things for a while.  You deserve it.


Please write me again and let me know how you are doing.

*Take a joke, people.  And why are you still reading my blog?

This Post Has One Comment

  1. Chicken

    Well, at least your jokes are getting better. 😉

    And everyone should go to therapy…. everyone- especially this chick.

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