How To Dump A Bridesmaid ... After The Wedding

In my best friend's greatest time of need, mere weeks after she helped me pull off a wedding beyond my highest hopes, I dumped her flat on her face.
03/23/2012 12:33 pm ET Updated May 22, 2012

So picture this: My best friend, a bridesmaid at my wedding who I've known since sixth grade and with whom I shared the following 13 years gossiping and partying and telling secrets, broke up with her longtime boyfriend the same week her favorite aunt died. You would think I, the devoted pal, would rush to her house with a pint of chocolate ice cream and a comfy shoulder on which to cry, right? You'd be wrong. In my best friend's greatest time of need, mere weeks after she helped me pull off a wedding beyond my highest hopes, I dumped her flat on her face.

It sounds harsh. I admit that. But the backstory, at least for me, puts it in perspective.

Ever since we graduated college in 2003, Jane had been unhappy with her life -- and she was never shy in sharing her sorrows. At first, I listened with a sympathetic ear. When she said she hated her living situation and wanted to move, I brainstormed ideas with her. She could go to Colorado and teach her favorite sport, snowboarding. Or she could take an internship in London, where she dreamed of living. Or she could even ship a few boxes to New York and room with me. Jane got excited by the ideas we bandied around, though never took a step to correct her very correctable situation.

The same held true of her job prospects. Jane held a fashion degree, but the corporate world frightened her. She never sent out a resume or went on a job interview and instead worked retail while bemoaning her circumstances. Take risks, I told her more than once, even if they're small and even if they terrify you. She always told me that I was right, that she just needed me to keep pushing her, that she would find an employment fit. That time has yet to come.

Much like the rest of her existence, Jane's romantic life flat-lined. She began dating Ryan the very night in 2005 that she met him at a local bar. He was nice enough and good-looking enough, but he already had one true love: music. Jane was a distant second to Ryan's band, and he made his hierarchy clear. Jane stuck it out because it seemed easier than meeting another guy in another bar.

All this was simmering at full heat by the time of my 2008 wedding. Though I was caught up in cake tastings and dress fittings and guest-list freak-outs, I still wanted to be there for her. I really did. The turning point came when a fellow bride-to-be asked how I had chosen my bridesmaids. I easily ticked off reasons for all my choices but faltered when I got to Jane. I had chosen her not because of our longtime friendship or because I couldn't imagine my day without her, but because she had asked and I had felt too sorry to say no. In that moment, I realized I couldn't be there for her until she was there for herself.

I know. Who was I to feel sorry? My life wasn't perfect, nor did I ever mean to imply it was. But after five long years of offering solicited advice knowing she wasn't going to take it, of sitting through dinners while she held back tears of aggravation, I finally understood that my role had changed. I was no longer the best friend. I was the enabler. Talking with me each week allowed Jane to air her frustrations and build up the courage to face another Monday. She wanted my guidance because she yearned to know there were ways out; she didn't, however, have the strength to follow those paths.

So when Ryan broke up with her and her aunt died, my first instinct, of course, was to bring over the ice cream and the shoulder. But I had to be tough when she couldn't. And so, in a desperate plea to move her forward, I first had to push her back. Hard.

I ate the ice cream myself (no more wedding dieting!) as I drafted a note: "Let me preface this letter," it began, "by saying that it's coming with the best intentions because I love you and worry about you." I outlined all the good I saw in her and how I cared too much to continue serving as her crutch. I wanted her to be happy, I wrote, and she needed to figure out what that meant. I asked her to call me when she was ready to talk. That was four years ago and she has not yet phoned. I don't know if she ever will.

Was it a terrible thing to do? Probably. My tactic was severe, for sure, but I don't regret my decision. If there's a chance she's living in a more meaningful way, I know I made the right choice. Ultimately, we were at a crossroads and I could pick between two paths: Jane's happiness or mine. I only hope she understands that I chose hers.

Oh, and that her bridesmaid dress is dry-clean only.

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