Dating a musician, providing he is Dan Costello, is a romantic adventure. Long ago, as newly-dates, we would drive all over—to Jackson Hole, to McCall, to Sun Valley—for wedding gigs, staying (not always sleeping…wink!) at whatever free lodging option came with the playing package.

The tradition continues 6 years later. A few weeks ago, Dan and his band, the Truck Stop Trio, headed up to Rocky Mountain Ranch in the Sawtooth Valley near Stanley, Idaho for a view-worthy wedding.

He plays, and wears hot western-infused outfits and hats. I am a hardcore groupie.
 I discretely chug Champagne. Victoria’s Secret grecian jersey dress (LUX). Angie snap button up (LUX).

Let’s hear it for the boys. Let’s hear it for the band.

And let’s hear it for the cheese tray. Hubbbbbba.

In sum, I may be dancing with myself, but time after time, it’s a total eclipse of the heart. Because love is a battlefield. Or just a pretty field, depending on your relationship.

High five for 80s dance music.

Ahoy matey. Welcome aboard the pirate ship…er…to the office for Story Story Night and Jessica Holmes Copywriting, where much mutiny and anarchy and unbridled cursing happens daily, but mostly in my mind. Conquistador painting by Toby Robin of Neighborhood All Stars ($125, Flying M art show)

Tenya by Laurieanne green silk shirt with gold buttons (<$20-with original tag for $250+, yikes! Buffalo Exchange, Portland). Country Suburbans parrot skirt (thrift store, $3). That is the best cheesy 80s brand name. Holy hell.

When I decided to go it alone (i.e. freelancing) 3 years ago after being laid off from an advertising agency, I didn’t realize the hardest part would be the vast and open and endless sea, sometimes calm, sometimes full of raging waters, where I am entirely responsible for and at the helm of my own little boat, with my little infinity awesome pen bird as my raised pirate flag, trying to find a way, and make it, and not get lost, or drown, or turn into a pillaging asshole.

Steve Madden bondage sandals (Ross Dress for Less). This sea feels so limitless and so oppressive all the time. And the work itself takes incredible focus and drive on a relentless daily basis. But I think of every day as practice for the place I eventually will be. Because it’s a pirate’s life for me.

And we’ll all float on alright.

In this post I will fail to show you this quite beautiful The Gilberts for Tally 70s pink disco dress (Acquired Again Antiques, Hyde Park, sale $28, original $40). I have already failed to post this on time. Story of my life.

First, meet the BPD officer who came up on stage during Story Story Night‘s FAIL: Stories of Mistakes and Misfires and told the audience that a packed bike rack outside was attacked by a slasher. Fail.

Too bad he didn’t show during featured storyteller Amanda Turner‘s story about not quite passing the sniff test for the police academy (hear her story).

Dudes, failure has defined so much about this whole rose period in my life, and I feel as if in the last few months all of my poor time and interpersonal management and other deeply embedded failures have been coming to a head. Saying, “Smell the roses, sista. And do something.”

After a lot of surface-level success undergirded by personal torment and much failure, I am essentially right back where I started from, but somewhere different. But it’s all good, in the end. And I am glad to be here. I am just ready to stop failing now.

So I am learning how to balance. Sometimes bloom. Then face another day to fail, fail, fail, and only then to win again. Armor Bijoux antique Afghanistani silver and glass necklace ($$$).

Also, I wear pretty things while I flop. It takes the sting off, just a little. Cindy Says heels: sale $60 (Original MSRP: $120, Piece Unique & Shoez).

I won’t fail to show you this dress for reals someday, promise.

Photos by Whitney Rearick.