The Guilt of Letting Go


By Jess Barone

It's really easy to feel guilty after a breakup - you were too young, too in love, moved too fast, too slow, you should've known better. You blew it, and you feel guilty as hell.

But imagine the relationship was a delicate, beautiful silk dress you found.

You feel so lucky. It's the prettiest dress you've ever worn. It has all the right qualities; it makes you look grown up and stunning, accentuates all your good features, and even brings to light features you didn't even know you could like, that you didn’t even know you had.

So you wear it a lot.

Over time you discover its faults; it hugs too tight in places to be truly comfortable, to let you really move freely. One of the straps is unreliable; the zipper nips at you and gets caught in your hair and it hurts. You ignore the imperfections.

You wear it out to parties, to work events, to the park. You get so many compliments from friends (even family)! You love it so much. But you've never had a dress like this before. It gets stains and tears. Some rips come out of nowhere, and you curse yourself for not predicting this would happen, for not trying to prevent it.

You clumsily try to mend it. But after each repair session, it seems to lose a little more of its luster. The fabric doesn't hug as snugly as it once did. Some of the tears are so big that even your best stitching can't truly make them disappear. The original beautiful material is marred from inexperienced overuse.

It makes you incredibly sad, because you have the photos to prove what it used to be like to wear that dress. How perfect it once was. It drives you crazy to hold the garment in your hands now knowing it's the same dress, but irreparably different.

You research home remedies and watch informational videos, ask your friends for suggestions - you even try to take the dress to a professional seamstress. You try your hardest, all the while wishing more and more "if only I'd taken better care of it from the start; if only I hadn't worn it so carelessly."

You had so many good memories in that dress. But now that it's tattered and patched and discolored, you don't take it out of the closet as much. You don't wear it out on nights with friends, or wear it home for family holidays. You don't want others to see the stains and threadbare parts.

Finally, you admit it's time to say goodbye. You love the dress, but you know it's beyond saving.

You box it up and give it to Goodwill. You know it will make someone else very happy one day. You know to someone, it will be perfect and they'll know just how to wear it.

You wear jeans for a while.

Then one day you'll pass by a shop and be mesmerized by what's in the window. You'll rush inside to try on the new dress, and it's perfect. It will bring out the best in you, and hot damn, you didn't even know you liked that new color so much. But son of a bitch, it's now your new favorite color. You will buy it with a smile on your face.

You can't feel guilty about that. You did try. It's a learning process. This time around, you know what to do to make it last.

writer photo

Jess Barone

Jess is a San Franciscan, serial Silicon Valley start up chaser and writer on the mend. She loves being outside, and when she's not skiing, she's camping on top of El Capitan, or planning for Burning Man nine months ahead of time.