Never let your girlfriend dress you

by Kevin on April 3, 2009

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So, my ex-girlfriend tried to “dress” me once. I came home from work and she had bought all these clothes for me. I was not expecting that at all. I was appreciative, but a little perplexed.

It wasn’t my birthday, and there was no real reason why she should be buying me clothes……then it dawned on me. She was ashamed of how I dressed.

Now, at the time, I was working two jobs. I managed a valet service in Nashville at a hospital during the day. My day started at 7:30am and ended around 4:30pm……I would then drive home….take my dog for a walk, and then return to work valet parking at a powerhouse restaurant from 5:30pm until about 9:30pm. I worked the day job 5 days a week, and the night job 6 nights a week. Not a great schedule, but what one does when they are trying to make a living, plus fund an independent artist habit.

When I wasn’t wearing my valet uniform…..i was wearing my usual boots and jeans with some sort of casual shirt. I’m a singer-songwriter……non-conformist, artist type. I wear what I wear. I don’t dress like a slob, but I tend to be an individualist, and maybe even a little eccentric in my tastes.

I will wear a pair of boots until they have holes in them out of loyalty.

She worked in the corporate world, and her friends were the young, hip, happening, fast crowd that comes from a certain area of Nashville called Green Hills-snooty. I did not fit in. So, if we ever hung out with them…….she wanted to be able to dress  me up like a ken doll……in some kind of uniform that would make me more “acceptable” within her circle of friends (as i’m writing this…..I really don’t even know why we dated in the first place, but she could be a really funny, sweet person, so I held onto that.

Anyway, she bought me an outfit that looked something like this:

Now, I have hairy, skinny, chicken legs, so I NEVER look good in something like this, plus, it was just not me.

To make matters worse……she bought some shoes that she expected me to wear with the outfit that were literally almost like pilgrim shoes. They were very nice………and i’m sure some individual on earth might have really appreciated them.  They were black suede with a huge buckle on each shoe……shocking really.

She expected me to wear them with the above outfit. They looked something like this:

or this
I had a terrible vision of myself innocently going to Kroger’s for some late night shopping in this outfit, and getting the crap beaten out of me by some rednecks if i’d actually worn it. In my mind, I might as well be wearing this:

So, this is all transpiring on a saturday afternoon. The next day, Gary Jenkins, my best friend in the world since college, who happened to be between girlfriends and alone that weekend, came over to go to lunch with us. We happened to have a Sunday paper sitting out on the dining room table……..and the Dillard’s Department store ads were showing with the usual medium market male model-Ken doll posing in the exact clothes that my girlfriend had just brought home to me!!!!!!!

Gary just casually picked it up and without prompting, or knowing that I had just had a new wardrobe suggested to me by my girlfriend……..said, “how come every girl I ever date tries to dress me like that guy?”

I disappeared into the bedroom, and put on the outfit along with the pilgrim shoes, and came walking out very slowly, and in a uncomfortable, my-mom-just-dressed-me-in-these-clothes-and-I-hate-them manner……………..Gary literally fell down on the floor laughing.
Gary is a comedian, and comedians usually never laugh at anyone eles’s jokes……….so, I felt pretty good about it.
My girlfriend didn’t. Soon after, I started going on the road for 3 months at a time in Europe and Australia, so that she would hopefully have an affair and hate me. It worked. Not sure about the affair, but we broke up soon after.

For a slightly more earnest post…..well, basically, a post where I talk about the fear that comes before creativity……check this out.
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When i’m not trying to make people laugh……..I do actually do music. I’m working on the new record now. Listen.
Read “Sometimes getting fired is not such a bad thing………”

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{ 10 comments… read them below or add one }

kevinmontgomery March 1, 2010 at 4:00 pm


kevinmontgomery March 1, 2010 at 4:00 pm

Mary, I reckon that has been my problem. I'm a total non-conformist!

kevinmontgomery March 1, 2010 at 4:01 pm

I love people like that. It is what makes the world go 'round! We even need the conformists!

kevinmontgomery June 11, 2010 at 3:32 am

Ha! Not laughing “with” me?

kevinmontgomery June 11, 2010 at 3:33 am

Exactly, Alisa!

kevinmontgomery June 11, 2010 at 3:34 am

Oh no! The family portrait!!!

John Radcliff February 18, 2011 at 1:49 pm

Hahahahaha! I shouldn’t laugh. I’ve been through this and it was every bit as shameful as it is funny.

V February 18, 2011 at 2:31 pm

oh…my…god…this post is my life with my gf!

kevinmontgomery February 26, 2011 at 9:08 pm

Get out while you can!!!!!!

kevinmontgomery February 26, 2011 at 9:08 pm

It is crazy. Never again!

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