Best Friend Engaged to a Creep

Dear Robin:

My best friend from college (“Kim”) divorced a year ago after a ten-year marriage (he left for someone else) and right away started dating someone else (“Chuck”) she met online.  None of her friends can stand this man: he is loud, obnoxious, rude, drinks too much, flirts with all the other women and is generally a giant douche bag, especially for someone almost 50 years old.

They went to Vegas for Thanksgiving and she came back sporting an engagement ring.  She tells me they are getting married on St. Patrick’s Day because they are both Irish. Classy.

She has no kids (she is 35) but he has four under 12, all of whom live with their mom. Thank God he had a vasectomy after the last kid.  She has a great job and owns her own home but he is an often-out-of-work software sales guy with child and spousal support.  I have noticed she ALWAYS picks up the check when we go out.

My question for you is should I keep my mouth shut, or should I tell my friend that marrying this guy is the biggest mistake she will ever make?  I don’t want to lose a friend but I feel weird not saying anything at all.


Dear Kathy:

Before you read any further, please click on the classic Elton John song, “Someone Saved My Life Tonight,” below:

Lyrics written by Elton John’s longtime musical partner Bernie Taupin, the words refer to Elton John’s engagement to his girlfriend in 1969.  Elton John was so distressed about the engagement (maybe because he’s gay?) that he considered suicide to escape the looming marriage.

His good friend Long John Baldry was smart and loving enough to convince Elton to break the engagement and pursue his musical career with full force and dedication.  Also, Elton was in love with Bernie, so the marriage would have been a challenge from the start.

Regardless, my point is that Baldry’s advice was so appreciated and on-point that Elton John credits Baldry for saving his life, AND he wrote an awesome song about him!

I want to address one specific point raised by your letter before I get to my advice, and that is the sexism inherent in your complaints about the financial disparity between Chuck and Kim.  For example: you noted Chuck doesn’t often pick up the bill.

If Kim has a lot more available cash than he does, I see no problem with that, nor do I think we should rule him out as a suitable partner because of his obligations to his children born from his first marriage.  The alimony is a slightly different story but Kim can try to contract around that – more on this in a moment.

If we are going to live in a truly equal society, we have to throw away the old construct that women should always marry “up” but never “down.”  Inherent in that paradigm is the notion that we women, child-like and helpless creatures such as we are, need someone to take care of us and that someone is a man.  I find such regressive reasoning outdated and insulting to my gender.


You have plenty of valid reasons to be concerned about this marriage, not the least of which is that he is a drunken boorish cad, so for the sake of your argument’s validity I would stick with the facts unrelated to his finances.

When we chatted last night you admitted you had never brought up your concerns about Chuck to Kim, even though they have been dating for several months.  I can understand why: your friend was fresh off a divorce, having a good time and you probably assumed she wouldn’t marry this guy so why rock the boat?

Now that she is engaged, it’s time to do that boat-rocking, but please be aware that your expression of your dislike of Chuck could very well result in the end of your friendship.  However, I think you know you can’t let her take this step without speaking your mind because it is just too serious a situation to ignore in the interests of keeping the peace.

First, take Kim to lunch.

No, on second thought, this talk requires a dinner.  Dinner allows for more wine and as usual with an AskDesCamp Talk by Numbers Conversation, wine is the lubricant that keeps the machine humming.

1. Ask Kim how she is processing her divorce and if she is over her first husband and the sudden end to their marriage via his affair.  Express sympathy and a concern that in her efforts to move past the pain she may be rushing into a second marriage without giving it the requisite amount of thought.

2. Ask her if she has truly reasoned through the aspects of being an instant stepmother to four young children.  Kim is in her mid-30s and certainly could still have children of her own.  I highly doubt she has thoroughly considered the implications of marrying an older man who cannot (without a very tricky surgery and even then the chances aren’t great) father any children she may want in the future.

3. Now for the hard part: express your specific concerns about his personality.  I am not above telling someone I think their beloved is an obnoxious prick if indeed he is one.  Tell your friend you love her and want what is best for her and you don’t think he is it.

4. Step aside and wait for the blowback.  People in love don’t like friends criticizing their partner choices.  I have to imagine Mr. Patience and Understanding dealt with a lot of this when we became engaged!


More specifically, people don’t like to hear hard truths.  In the past few years I was compelled to be brutally honest with two friends who I saw making catastrophic decisions in their personal lives.

One rejected my advice and never spoke to me again (her life subsequently went to complete and utter shit because of those exact decisions I was advising her against) and the other took my thoughts to heart and felt no anger towards me for expressing them, but rather gratitude that I raised issues he had not been able to see for himself.

The important takeaway for you, besides the fact that this blog is indeed all about me, is that unvarnished honesty must come with the realization that your words may either end the friendship or at least strain it for a significant period of time.  Many of us, myself included, go through periods in our lives when we cannot bear to face the truth inherent in our bad decision-making.

For people in your position, a decision must be made whether you value the friendship more than the friend.  Think on that for a spell.

5. If you can’t dissuade her from the marriage, help her find an attorney who can draft a pre-nup that will stand up in court in the inevitable divorce.  First, she should have one to protect her assets acquired before the marriage.  For example, you told me she owns a home.  I would want to carve that out in a pre-nup if I were her, including any subsequent increase in value.

Second, in many states she could end up paying Chuck’s alimony if he loses his job, because the courts will look at “total household income,” not just his income.  While a pre-nup may not be able to totally protect her in this circumstance, it’s better than nothing.  Many second wives unwittingly find themselves the target of first wives who feel that in the event the ex-husband can’t afford the welfare alimony anymore, his new love should pick up the tab (rather than Wife #1 actually earning a living).


Finally, advise her to keep her assets absolutely separate from Chuck’s (such as they are, anyway), even if they have a good prenup.  They should not co-mingle any funds, have a joint checking account, etc.  This will help her cause when she objects to Starter Wife’s discovery motions seeking information on Kim’s salary, the value of her home, how much she spent on Chuck’s birthday party and how much she paid for her labradoodle.*

6. If Kim takes a step back and does not go through with the marriage, you damn well better be there for her when she is lonely and needs a shoulder to cry on.  Be more than a friend – be a comprehensive support system.

7. If instead she marries this man, I offer the same advice as above.  Something tells me she is going to need a good friend if she goes through with this lunacy.

You have very little time to get your message across so start today.  Please let me know how it goes.


*I wish I were joking but requests like this are not only unheard of, I have seen them.