Shopping 101 or Breaking Up Is Hard To Do

This morning, I entered my inner sanctum (a.k.a closet) hopeful for a miracle.

What kind of miracle? You know, the kind where that unloved article of clothing you’ve never worn suddenly is exactly what you need.

Glancing around, the first thing that caught my eye was a pair of gorgeous but one-size-too-small pants I picked up a few years back. I'm not sure what I was thinking when I bought them. Maybe that I'd finally lose those last few pounds and they'd suddenly fit perfectly, like a glove? As if.

And then there's the fabulous wool sweater I snagged at TJ Maxx. It was discounted so many times they were practically paying me to buy it. Even though, it felt like sandpaper when I tried it on, who could resist getting a three hundred dollar sweater for 15 bucks? Maybe clothing, like fine wine, improves with age. I told myself, one day I'd put it on and it would be baby-skin soft.

I'm still waiting for that day. If only there was a morning-after pill for bargains gone wrong.

At least half a dozen times now, I've sincerely tried to give away these painful reminders of what was I thinking? It always plays out the same way.

First, I'll grab a full-size trash bag. Not one of those wimpy kitchen ones. No, I'm going all the way this time, I tell myself. Bag in hand, I courageously enter the closet and begin the fashion inquisition.

“Have I outgrown you, are you outdated, will I ever wear you again?"

My favorites beam back at me through their cellophane wrappers, proof positive that they are truly loved because I take extra precaution to keep them safe. It starts to get harder when I get to the things I only wear occasionally, or that I've worn too much. Still, with each one I can imagine wearing them again, or at least one more time. This black dress might be a little too short now, but I wore it to that amazing party - the one where I danced all night long, ate too many desserts and didn’t gain an ounce! I can't possibly give that away.

Finally, I get to the whole point of the exercise - all of those purchases gone wild. 90% off, who could resist such a deal? Apparently, not me.

I pause on each article of clothing and try to imagine wearing them...one day...in a not too distant future. Maybe I will be invited to an event where this is the only perfect outfit. Plus, I have 3 different sets of jewelry to pair with it so it must have value. Doubt encircles and that little nagging voice “you’ll be sorry". Sometimes I'm strong enough to carelessly toss the item into a bag. Yes, carelessly, because if I express any hesitation the clothes will try to convince me to let them stay.

After an exhausting emotional battle with my closet, I stand there with a mostly-empty bag resting near my feet, filled with a mixed amount of desire and despair. I start to have second thoughts. With a sigh, I tenderly remove the cast-offs and hang them up again. And so the cycle begins anew.

How long do you hold onto a bad buying decision before letting it go?

Maybe that’s what retail therapy should really be about - the relationship between the buyer and the bought. Breaking up is hard to do, even when the object of your affection doesn't excite you like it used to and never really quite fit you in the first place.

Readers, please share your tips on how to let go without feeling the empty-hanger syndrome. How do you say goodbye to a good buy?

And by the way…what’s in your closet?