Speak My Mind or Hold My Tongue?

Dear Robin-

My friend Shelby has been divorced for a few years, is lonely, and wants to find a new man.  Her ex has moved on, and when I say moved on I mean he’s remarried with a baby on the way.

This is especially hard on her because the marriage ended suddenly when her ex announced quite to her surprise he never wanted children, EVER.  She very much does but since her divorce hasn’t met anyone worthy of this aim, until recently when she met a guy she really likes named Rick.

Rick has some major baggage. He’s separated from his wife and has 2 small children. His family lives out-of-state and he has been working 4 days a week in Seattle (where we live). During this time Shelby has been spending a lot of time with him and is falling hard. He seems to really care for her too, although I haven’t spent a lot of time around them both so it’s hard to guess.

Also, even though he is separated when his wife found out he was dating her she freaked out so he had to race home to deal with the fallout.  

I am not sure what to say to her when she asks my advice about the situation. He won’t leave his kids to move to Seattle so what are her options, really? Just to get more and more wrapped up with him, only to have it fall apart miserably and put her back at square one?

I’d like to say something firm to her, but don’t want to sound unfeeling and hurt the friendship. Can you help?

Thanks much,


Dear Alicia:

American author and all around hottie Wes Moore once noted

“People need to think that you care before they care what you think.”  

I wish I thought of that one first, damn it.

Whether or not your advice carries any weight with your friend is debatable, but so long as she understands you are coming from a place of love and support I think you can impart your feelings to her without unduly straining the friendship.  

Therefore, your first objective should be to make it clear you want what is best for her and you are not criticizing Rick but rather making a pointed observation about the divergence between this relationship and her stated life goals.

There is certainly nothing wrong with a short-term dalliance so long as that is either the objective of both parties or the folks involved are OK with being hurt.  We know Shelby’s objective is to remarry someday and join the Pudding Club and we also know she has had enough of getting hurt lately.

Rick may be a hell of a nice guy, but he is unsuitable for several reasons:

  • He doesn’t live in Seattle; 
  • He is not divorced;
  • His wife seems to be under the impression that there is still a breath of hope living in their marriage despite the separation; 
  • He has young children;
  • He doesn’t live in Seattle. Yeah, I know I mentioned that, but it deserves another nod because she has no contacts in his hometown (but would consider moving) and there is zero chance he will leave his kids.

We all have one carry-on and some personal items, but Rick’s baggage fills up the hold.  I see their chances at a long-term successful relationship at exactly 0.0%.  Why?

Shelby is a JumpOff, pure and simple: the convenient vehicle by which he can ride to his new single status with as little emotional upheaval as possible.  


Some people immediately jump into a “relationship” when they separate from their spouse because it’s easier than processing what is happening to them.  It’s emotionally and intellectually lazy and never serves the purpose of avoiding the grief that comes with divorce but rather merely puts it off in time.  

Also, the sex is amazing.

Shelby has been through a tough rejection: her ex said he didn’t want to have children but what he really meant is he didn’t want to have children with her.  So why would she now subject herself to an almost certain heartbreak with a man who has little to offer her besides putting his bow in her quiver?

Perhaps Shelby can better compartmentalize her emotions than I can: maybe she can enjoy the ride for what it’s worth and move on when he leaves.  Maybe it’s true it is better to have loved and lost Rick than to back away now.  The problem with that is she’s cutting herself off from other opportunities as she falls deeper into this “relationship.”


Sometimes it’s easier to deliver hard advice in a metaphor. Or simile. Or is it analogy? Who knows – I’m an advice columnist, not an English professor.  

What I do know is it would be ill-advised to call her a JumpOff.  It sounds crass and cruel so let’s package your advice in a palatable form she can digest more easily.

I asked you what Shelby’s dream job would be and you told me her dream is to be a top-notch graphic designer: a leader in her field.  Using Shelby’s professional goals to draw comparisons with her personal ones may help her see that Rick just isn’t the guy for her.

In short I’d put it this way:

“Shelby, imagine you have a great job offer at the best graphic design company in Seattle working for a creative team of professional for more money than you have ever earned.

“So why are you filling out a job application to work at McDonald’s?”

Yeah, it really is that simple.  And like I said, let her know your opinion is borne from all she has told you about what she yearns for in her personal life and you only want her to be happy.

Then be there to serve her wine and wipe her tears when it ends badly, because the heart and the head rarely get along well enough to make a good decision together.  




This Post Has One Comment

  1. A Loyal Fan

    Sometimes, just sometimes, against all odds (San Francisco in our case), it works and 12 years later, it’s still working.

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