Don't marry him! He's no good!

We all agree our best friend will be making a mistake if she marries this guy, but should I tell her?

Published August 12, 2010 1:01AM (EDT)

Dear Cary,

Your book has been a reliable and trusted friend in my life. The edition I have is now well-worn and dog-eared, but has provided so much clarity in what has been a tumultuous few years for me. I am writing you now because I need a fresh perspective and some sage advice -- I'm too close to this problem to know what to do.

My friend (let's call her CJ) has been in a relationship for over three years. She is part of an incredibly close circle of mostly female friends in their mid- to late 20s who care for her deeply and think the world of her. Throughout this relationship, there have been many conversations behind her back about the relationship between CJ and her boyfriend, whom we'll call "Randy." CJ is a beautiful girl (oozes pinup sex appeal), whip-smart (has her master's and a great full-time job), and is hysterically funny. Randy, on the other hand, is ... an odd one. He is humorless, has nothing approaching a job, and almost never talks. I'm not exaggerating. A typical meal out with them usually involves him staring off into space, making a fuss about the food not being right, and then grunting a goodbye. He is controlling (especially about her weight) and has just always made me uncomfortable in that indefinable but undeniable way. Mostly it just comes down to us all feeling that she could do so much better. She's a total catch! When he was out of town for a few weeks not long ago, it was the happiest we'd seen her in years. CJ will sometimes talk to us about her frustrations about how unsocial he is or that she's sick of completely supporting him financially, but it's hard to get her to open up about their relationship.

Our group of friends were all at their house yesterday celebrating CJ's birthday when out of nowhere, her boyfriend drops down and spits out a proposal so fast I thought at first he had just tripped and fallen on one knee. The mood in the room was utter shock -- we were horrified enough before by the vague idea of them getting married. Besides blindsiding her with this in front of a big group of people (half of whom he didn't know!), she clearly was terrified. She went white and started shaking so badly she had to sit down. It was a shock, without any of the much-hoped-for jubilation that should come along with a proposal.

However, she said yes to the proposal in front of all of us.

After departing, our friends quickly recongregated at a different house so we could all freak out together. The consensus is: This is going to ruin her life. We know CJ, though, and for a lot of complex reasons she feels if she's not married with kids by 30 she has somehow failed. There is pretty much zero chance she will back out on her own.

We pride ourselves on being best friends! Smart and loyal women who would never let petty drama ruin anything! But how can we possibly live up to that if we talk behind her back about feeling like we're slowly watching her spirit die out via this relationship, but then not actually tell her ourselves?

So the question is, who should tell her and how? For various reasons I seem like the logical choice. I want to tell her. I've wanted to tell her for a long time now and the engagement has made me feel like it's now or never. What I want to tell her is this: "I love you. I don't feel like I've seen you be your true self or grow with him, and I worry that you're doing this because you feel you need to be at a certain place in life and not because you really want to. Even though he asked you in front of all of us and now everybody knows, you do not have to do this. All that I ask, and all that your friends want, is for you to do what's right for you, and we would never judge you for walking away. I will always support you and be there for you, but I think marrying him is not what is best for you. Deep down I think you know all this, and I'm sorry if this is hurting you."

If I do this, I will do it with as much tact as possible and make it about her and not about disliking Randy. Yet I know that I am absolutely risking the end of our friendship. Even if she agrees with me deep down, I think this may upset her to a point where she hates me, even though I think I'm doing what a true friend should do.

My circle of friends has been somewhat hard to get a read on. At first everybody was gung-ho on the idea, but since logging into Facebook this morning and seeing they decided to tell everybody about the engagement, now we don't know what to do. We thought we had time to strategize. I am going to write the letter only from me and not mention that "by the way, your friends all feel this way." I know that they will be somewhat honest with her as to their concerns, but I'm going to be the one out on a limb telling her I think she's making a mistake. Everyone is devastated by the idea of them marrying, but I may be the only one voicing it.

I'm convinced that she will quickly have a child as the only way to justify this to herself, and then will never get a divorce, since for her that would be the ultimate "failure."

What does being a true friend mean? I think she's throwing her life away for somebody who will never do her justice. But at what point am I doing it for myself and not for her? Do I risk one of my closest friendships in the attempt to throw her a lifeline she may reject?

Bridesmaid or a Better Friend?

Dear Bridesmaid,

I say do it. Take the risk.

The bigger the stakes, the more important it is to step forward and try to avert catastrophe.

Marriage is up there with the highest-stakes decisions you can make. It's like, Should we invade Poland? It's not the kind of thing you keep quiet about, even if speaking up has consequences.

So I'll be interested to read, in the comments section, what others think, and especially what experiences others have had in such matters.

This is a short one because that's really about all I have to say on it. I think you should say what you have to say and see what happens.

I salute you for doing so.

The Best of Cary Tennis

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