Friendship Suffering: I Hate His Girlfriend!

Dear Robin:

I have a long time pal of 35 years who is living with a woman I can’t stand. She is after his money, he knows it yet is too weak to care. I am incredibly disappointed in him as I have brutally frank about what I think of her. I am ready to throw our relationship into the trash bin. What are your thoughts?

Pissed in Portland

Dear Pissed:

I love your question because it shows both that men go through friendship problems too and that they tend to be more succinct than the fairer sex.  Unfortunately for you, I am not a succinct person so you will be forced to wade through paragraphs of my brilliant thoughts before I give you my advice.



I know the woman of whom you speak, and it is a well-known fact that she has fucked every wallet at the Multnomah Athletic Club.  While her previous victims wised up eventually, your friend (let’s call him Bill) has neither the self-esteem nor the will to boot this gold-digger (Goldie) from his home.

When you and I chatted, you mentioned that Bill had languished in a very unhappy marriage for many years, and it ended not with a divorce but with his wife’s death.  Lucky man.



Apparently it didn’t take long for Goldie to set her sights on Bill, and she went after him with the intent and fervor John Travolta engages in an all-male bathhouse.  Seeing as how she began her campaign before the wife actually died (she was sick for a long time and it was generally known her death was imminent) it seems pretty obvious she has put some thought into this endeavor.

Shit, I gotta give Goldie some props here.  Most gals would wait until the body was disposed of and bring around a Sympathy/I’m Available Casserole – this woman hopscotched backward and began the chase early enough to help pick out the wife’s funeral dress.  That shows ingenuity and drive, two characteristics not normally seen in gold-diggers.


I have a few thoughts on your friend so put on your readers and pay attention:

1. He suffered for years in a loveless marriage and never had the guts to leave;

2. He is a great guy but has always been a wee bit of a pussy;

3. He let his first wife push him around and continues this pattern with Goldie; and

4. He has no confidence when it comes to women, which is odd because he’s handsome and successful.

I gotta tell you, even if Bill broke up with Goldie I strongly suspect he would end up in a nearly identical situation with the next woman.



There are people in the world who don’t think they deserve to be happy, and a common manifestation of that condition is the repeated pattern of partnering with unsuitable people.  I don’t know Bill personally but I would not be surprised to learn he had a difficult relationship with his mother.

As of press time, you were not able to confirm or deny this assumption so let’s just go with it because it’s easy: his mommy hated and abused Bill and as a result, his preferred partner paradigm is an unloving bitch who is using him for his money.  That’s a tough pattern to break, but not impossible.  More on that later.

My advice for you is two-pronged, so if Part A is unsuccessful you move on to Part B.

Part A of AskDesCamp’s ingenious advice to Pissed in Portland:

Set her up and watch her fall.


You know when and where she works out every day.  Hire an actor, a really good-looking one, to accidentally bump into her outside the club.  Make sure he is dressed extremely well in fine expensive threads and most important: beautiful shoes.

A bona-fide gold-digger will assess the man from top to bottom, and shoes are often the giveaway of a man who dresses like he has money but really does not.  This is gold-digging 101, people, get with the program.

Your actor’s job then is to charm the panties off this woman and get her to agree to meet for coffee, during which time he will explain he just moved here from San Francisco after selling his software company to Microsoft.

He is a widower (no alimony, which is important to a professional Goldie) and has too much time and money on his hands, so he is considering starting a winery in Yamhill Valley.  In short, he is irresistible.



His job is to seduce Goldie over time (I suspect it won’t take long) and get it on tape.  I don’t mean a sex tape, because as I mentioned I know Goldie from the club and let’s just say I’m not sure how she keeps attracting these wealthy guys – nobody wants to see her sex video.

He just needs to get her on tape talking smack about poor Bill and expressing her affection for this man whom she thinks is another step on her ladder to wealth and prestige.

Then you take Bill out, add whiskey, and play the tape.  Is this wrong?  Is this underhanded?  I sometimes wonder if I may have lost my moral compass…



There are three possible outcome here:

1. Bill wises up, kicks her out and gets some counseling (or just have him call me to knock some sense into him) so he can recognize this destructive pattern in his life and fix it; or

2. She doesn’t fall for it, in which case you engage Part B; or

3. She falls for it and Bill doesn’t break up with her, in which case you also engage Part B.



Part B of AskDesCamp’s ingenious advice to Pissed in Portland:

Don’t give up on your friend.  He needs you.

You’ve known Bill for a long time and he’s been through a lot over the past few years.  He may be a wimp with remarkably low self-esteem, but he’s still your friend.  35 years is a long time and with all the memories and good times you have shared together, it would be a shame to write him off because he has horrible taste in women.

In fact, I don’t think it’s much of a stretch to say your abandonment of Bill would be playing right into Goldie’s hand.  The more she can isolate him from his true friends, the better position she is in to become his sole source of emotional support and in turn the less likely he is to recognize how awful she is and dump that bitch.


You’ve said your peace (piece?) so let it go and be there for Bill when he needs you.  I know how much you hate Goldie, so part of me wants to suggest you only see Bill on his own and away from her.  However, I’m a horrible person, so I have another idea:

Be around.  Be around A LOT.  Show up unannounced with some wine and photos of you and Bill “back in the good old days.”  Annoy the shit out her.  Put your feet on the coffee table and since you smoke on occasion and she hates smokers, light one up in the living room and flick the ashes into the nearest orchid.

I have a strong sense that she likes you about as well as you do her, so it may be fun to fuck with her head and make some funny comments about gold-diggers when she is around.


For example:

“Hey, Goldie!  Did you hear the one about the South African gold miner who was injured at work and had to have his right leg amputated?  After the operation he was talking to a fellow miner and said, ‘I suppose I’m fucked now, who would ever want a one legged gold digger?’

His mate replied, ‘Try Paul McCartney.’

heather one leg mills

That’s a good one, right Goldie?  Oops, sorry, too close to home?”

Either way, whether in her company or without, be there for Bill and don’t toss the friendship in the bin just yet.  Perhaps someday you will be able to make him see that he is worthy and deserving of an equal and loving partnership with someone who isn’t using him.

I’d keep trying if I were you, and please write back and let me know how the plan to trap her goes.  I’d love to be a part of that if possible…



This Post Has 5 Comments

  1. ali whiting

    Plan B all the way. You don’t drop friends because you don’t like their current partner. Ever. You show up, you discuss past, really fun and crazy times – which completely excludes her. Again and again. Treat them to dinner, a play, whatever. Get tickets to sporting events (or poetry readings – whatever floats your boat) that she’ll hate so she’s forced to sit through them while you have a wonderful time with your friend – all the while ignoring her.

    Plan A? Nah. Bad call. It’s not good form to humiliate a friend. And be a witness no less. Although making comments about a fictitious attractive woman that you considered spending time with but decided that you deserved better than sloppy thirds, or didn’t want to always wonder how you’re sizing up compared to the 30 before you while sitting with both of them might be a fun alternative. May make Bill think for a minute and should piss Goldie off.

  2. Pissed in Portland

    Honestly I am not going to abandon my friend. that being said I will see him less as a result of his relationship and I won’t ever get together with the two of them. At my age life is too short to hang around a couple that sucks together like they do.

  3. Debbie

    I will personally fly into Portland to help coach the mole in the rich guy scheme. Love it!!!!!!! You are so evil…. I love it!!!!

  4. Chicken

    It’s when you start analyzing the parent/ childhood relationship shit that you lose me…. I hear ya on some of it, but I don’t think everyone’s issues go back to their relationship (or lack of thereof) with their parents.

    1. askdescamp

      I agree in this case because I found out after posting I was wrong. Critique noted.

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