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Never let your girlfriend dress you

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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arrow60 Responses

  1. everysandwich
    74 mos, 3 wks ago

    I hate to laugh at your past pain, but, but. HAHAHAAHAHAHA!!! Oh, man. That played like a movie scene in my head. Some of the pics above didn’t work for me. Maybe yo can photoshop yourself into an approximation of your boyfriend uniform?

  2. 74 mos, 3 wks ago

    dude, i’m just glad i got out alive.

  3. 74 mos, 3 wks ago

    dude, i’m just glad i got out alive.

  4. ChicagoBeth
    74 mos, 3 wks ago

    Fun! Reminded me that there exists a picture of me and my then-fiance in 1965 wearing matching Madras shorts and polo shirts. Strangely, I think we both thought we looked good!

  5. ChicagoBeth
    74 mos, 3 wks ago

    Fun! Reminded me that there exists a picture of me and my then-fiance in 1965 wearing matching Madras shorts and polo shirts. Strangely, I think we both thought we looked good!

  6. everysandwich
    74 mos, 3 wks ago

    I hate to laugh at your past pain, but, but. HAHAHAAHAHAHA!!! Oh, man. That played like a movie scene in my head. Some of the pics above didn’t work for me. Maybe yo can photoshop yourself into an approximation of your boyfriend uniform?

  7. 74 mos, 3 wks ago

    Dude…HILARIOUS!….I totally remember that day! What are the odds? She had to believe you prompted me to say what I said. Oh well, as with all painful things, that too did pass. Fun-ny. Man, you are wrong. You always make me laugh. I mean, I’m always laughing at you. I kid you not, I had some of those Pilgrim buckle shoes. They matched the hat.

  8. 74 mos, 3 wks ago

    Dude…HILARIOUS!….I totally remember that day! What are the odds? She had to believe you prompted me to say what I said. Oh well, as with all painful things, that too did pass. Fun-ny. Man, you are wrong. You always make me laugh. I mean, I’m always laughing at you. I kid you not, I had some of those Pilgrim buckle shoes. They matched the hat.

  9. 74 mos, 3 wks ago

    Kevin, trust me – it’s funny!

  10. 74 mos, 3 wks ago

    Kevin, trust me – it’s funny!

  11. KittyKat
    74 mos, 3 wks ago

    It’s not the cloths that makes the person it’s what is in the heart and who they are. Poor guy. But it was funny…

  12. KittyKat
    74 mos, 3 wks ago

    It’s not the cloths that makes the person it’s what is in the heart and who they are. Poor guy. But it was funny…

  13. Gaynor
    74 mos, 3 wks ago

    :O)))) TOO FUUNY!! THAT’S A CARDINAL RULE THOUGH … NEVER change for anybody!! It just doesn’t work!! BUT you must have a photograph somewhere eh?? … ;O) Now it’ll forever be ‘Kenny Montgomery’ you realise!! HA!! Gaynor giggling ratter a lot :o ))

  14. Gaynor
    74 mos, 3 wks ago

    :O)))) TOO FUUNY!! THAT’S A CARDINAL RULE THOUGH … NEVER change for anybody!! It just doesn’t work!! BUT you must have a photograph somewhere eh?? … ;O) Now it’ll forever be ‘Kenny Montgomery’ you realise!! HA!! Gaynor giggling ratter a lot :o ))

  15. 74 mos, 3 wks ago

    Yes, kitty kat……….that is the point…..i just wear what i wear………..and am completely comfortable with that.
    She wanted something that i was not, and that is fine, too.

  16. 74 mos, 3 wks ago

    Yes, kitty kat……….that is the point…..i just wear what i wear………..and am completely comfortable with that.
    She wanted something that i was not, and that is fine, too.

  17. Annabelle
    74 mos, 3 wks ago

    I’m picturing those pilgrim shoes with white shorts…UGH! Looks very G-A- double Y’-ish to me or like something Alec Baldwin would wear! You’ve got a talent for descriptive writing Kevin!!

  18. Annabelle
    74 mos, 3 wks ago

    I’m picturing those pilgrim shoes with white shorts…UGH! Looks very G-A- double Y’-ish to me or like something Alec Baldwin would wear! You’ve got a talent for descriptive writing Kevin!!

  19. 74 mos, 3 wks ago

    Bahahaha! Seriously hysterical, Kevin. That said…when I first met my ex-husband, he dressed something dreadful…and was trying to be a successful musician. Not that you have to have a certain “style” to perform, but he was pretty far from stage-ready. He eventually let me “make him over” and after picking out his clothes for the next few years he eventually caught on. I just helped him match his clothes with his personality–relaxed and casual, but not ratty. Ha, but I never tried to make him waspy ;) .

  20. 74 mos, 3 wks ago

    Bahahaha! Seriously hysterical, Kevin. That said…when I first met my ex-husband, he dressed something dreadful…and was trying to be a successful musician. Not that you have to have a certain “style” to perform, but he was pretty far from stage-ready. He eventually let me “make him over” and after picking out his clothes for the next few years he eventually caught on. I just helped him match his clothes with his personality–relaxed and casual, but not ratty. Ha, but I never tried to make him waspy ;) .

  21. loulou
    74 mos, 3 wks ago

    Glad to hear she is your ex ..why try to change someone who you were quite happy with when you met ?????..anyway cant imagine any man wearing them cloths??? lol x do you think it a test of how much do you love me ha ha …could you ever love a woman THAT !!!much ha ha x

  22. loulou
    74 mos, 3 wks ago

    Glad to hear she is your ex ..why try to change someone who you were quite happy with when you met ?????..anyway cant imagine any man wearing them cloths??? lol x do you think it a test of how much do you love me ha ha …could you ever love a woman THAT !!!much ha ha x

  23. 74 mos, 3 wks ago

    Jaime, yes, that is what she was trying to make me. I hate those “uniforms” that people where to denote their lifestyle or place in the world.
    Of course, i reckon they would say that i was wearing a uniform of sorts………i’m not sure what it is, but it’s just me. Random.

  24. 74 mos, 3 wks ago

    Jaime, yes, that is what she was trying to make me. I hate those “uniforms” that people where to denote their lifestyle or place in the world.
    Of course, i reckon they would say that i was wearing a uniform of sorts………i’m not sure what it is, but it’s just me. Random.

  25. Stevie
    74 mos, 3 wks ago

    I have to ask, what were doing with her in the first place?

    That was never going to work. But then some of my choices haven’t been that good.

    That’s excluding my wife. I did okay on that one. Thankfully.

  26. Stevie
    74 mos, 3 wks ago

    I have to ask, what were doing with her in the first place?

    That was never going to work. But then some of my choices haven’t been that good.

    That’s excluding my wife. I did okay on that one. Thankfully.

  27. 74 mos, 3 wks ago

    Hahahahaha… funny all girlfriends want to dress their boyfriends and all boyfriends want to dress themselves. That’s yet another conflict between the sexes. Although I’m with you here. Your cowboy look is way sexier than the preppy boy look she picked for you. I think you just got paired up with the wrong girl (apparently so, since she’s now your ex). Perhaps if she was the right girl for you, she would have picked out a more flattering outfit!

  28. Alisa Bowman
    74 mos, 3 wks ago

    Hahahahaha… funny all girlfriends want to dress their boyfriends and all boyfriends want to dress themselves. That’s yet another conflict between the sexes. Although I’m with you here. Your cowboy look is way sexier than the preppy boy look she picked for you. I think you just got paired up with the wrong girl (apparently so, since she’s now your ex). Perhaps if she was the right girl for you, she would have picked out a more flattering outfit!

  29. Neil Newton
    74 mos, 2 wks ago

    My wife still tries to dress me – but not so much these days. Even she is starting to lose heart. She mentioned a family portrait the other day – now that DOES scare me..
    A friend of mine once told me about a colleague that decided he would never wear a different style of shoe. He worked out how long a single pair lasts, and how long he was likely to live, then went out and brought a lifetimes supply…. Freaky or farsighted ?

  30. Neil Newton
    74 mos, 2 wks ago

    My wife still tries to dress me – but not so much these days. Even she is starting to lose heart. She mentioned a family portrait the other day – now that DOES scare me..
    A friend of mine once told me about a colleague that decided he would never wear a different style of shoe. He worked out how long a single pair lasts, and how long he was likely to live, then went out and brought a lifetimes supply…. Freaky or farsighted ?

  31. 74 mos, 2 wks ago

    Yes, i never should have been with her in the first place……..she was the antithesis of what i’m about.
    I probably wouldn’t mind her dressing me if she didn’t try to dress me like an ex-frat boy.
    Bleck.
    Kevin

  32. 74 mos, 2 wks ago

    Yes, i never should have been with her in the first place……..she was the antithesis of what i’m about.
    I probably wouldn’t mind her dressing me if she didn’t try to dress me like an ex-frat boy.
    Bleck.
    Kevin

  33. Margaret
    74 mos, 2 wks ago

    Sooo funny! Just a quick insight to her motivation–she loved you and wanted her friends to see you as she saw you. Your everyday “whatever” clothes may not have impressed her shallow status-seeking college buddies, so she just wanted them to realize how wonderful and promising you were . Unfortunately, if they couldn’t see past the “uniform,” they missed out and their loss. Too bad (for her) she chose them over you, but it takes all kinds. Love you! Don’t ever change!

  34. Margaret
    74 mos, 2 wks ago

    Sooo funny! Just a quick insight to her motivation–she loved you and wanted her friends to see you as she saw you. Your everyday “whatever” clothes may not have impressed her shallow status-seeking college buddies, so she just wanted them to realize how wonderful and promising you were . Unfortunately, if they couldn’t see past the “uniform,” they missed out and their loss. Too bad (for her) she chose them over you, but it takes all kinds. Love you! Don’t ever change!

  35. 73 mos, 3 wks ago

    Hahahahahahaha…the part where you came walking out and the friend dies laughing! The vision is a gut buster! Yeah, she must have thought his comments were rigged. Just hilarious!! I agree with the rest…she was not the one for you. Best to stay with your own personal style!

  36. 73 mos, 3 wks ago

    Hahahahahahaha…the part where you came walking out and the friend dies laughing! The vision is a gut buster! Yeah, she must have thought his comments were rigged. Just hilarious!! I agree with the rest…she was not the one for you. Best to stay with your own personal style!

  37. Kelly Goodrich
    73 mos, 2 wks ago

    Kevin~ i just now read this story and I cannot stop laughing…..great mental picture going on in my head of you modeling your new clothes for Gary. Reminded me of when I met my ex-husband (alot of those stories, huh?) in the late 1980′s and he was a non-conformist musician….beyond “individualist”…beyond “bohemian”…beyond homeless looking! I only wanted what was best for him~not to embarrass either of us -haha!! He begged me not to buy him “matching garanimals type stuff”, but me (being the cool gal that I am) actually bought pretty “groovy” (his word) stuff….and 20 years later – when I see him for our children-swapping – he’s still wearing the stuff!!!! Horrors!

  38. Kelly Goodrich
    73 mos, 2 wks ago

    Kevin~ i just now read this story and I cannot stop laughing…..great mental picture going on in my head of you modeling your new clothes for Gary. Reminded me of when I met my ex-husband (alot of those stories, huh?) in the late 1980′s and he was a non-conformist musician….beyond “individualist”…beyond “bohemian”…beyond homeless looking! I only wanted what was best for him~not to embarrass either of us -haha!! He begged me not to buy him “matching garanimals type stuff”, but me (being the cool gal that I am) actually bought pretty “groovy” (his word) stuff….and 20 years later – when I see him for our children-swapping – he’s still wearing the stuff!!!! Horrors!

  39. Mary
    73 mos, 2 wks ago

    Holy crap!! HAHAHAHAHAHAHAHAAAAA I finally got to read the ‘pilgrim shoe’ story!! (It was pretty awesome, by the way.)

    Yeah, totally cannot see you dressing like that. In fact, I think there are way too many who do dress like that and should be stopped, but what can you do?? I once dated a pro-golfer who expected me to dress like what he thought the girlfriend of a pro-golfer should dress like, I guess. Kind of the female equivalent of what you described above. It was awful. And just another reason our relationship did not last the summer.

  40. Mary
    73 mos, 2 wks ago

    Holy crap!! HAHAHAHAHAHAHAHAAAAA I finally got to read the ‘pilgrim shoe’ story!! (It was pretty awesome, by the way.)

    Yeah, totally cannot see you dressing like that. In fact, I think there are way too many who do dress like that and should be stopped, but what can you do?? I once dated a pro-golfer who expected me to dress like what he thought the girlfriend of a pro-golfer should dress like, I guess. Kind of the female equivalent of what you described above. It was awful. And just another reason our relationship did not last the summer.

  41. sherry
    73 mos ago

    Hilarious! Since I grew up in the Franklin and school in Green Hills, I could picture exactly what you were talking about.. Some of the guys driving pickups at the Franklin ‘s Kroger would had given you a hard time ( Mt juliet Too) and the guys at the Green Hills’ would had tried to show you a good time dressed like that . Honey, I have always liked Your style..never conform…

  42. sherry
    73 mos ago

    Hilarious! Since I grew up in the Franklin and school in Green Hills, I could picture exactly what you were talking about.. Some of the guys driving pickups at the Franklin ‘s Kroger would had given you a hard time ( Mt juliet Too) and the guys at the Green Hills’ would had tried to show you a good time dressed like that . Honey, I have always liked Your style..never conform…

  43. 71 mos, 3 wks ago

    this makes my weekend… I have laughed at you guys for at least an hour…

    *thank you for that*

  44. 71 mos, 3 wks ago

    this makes my weekend… I have laughed at you guys for at least an hour…

    *thank you for that*

  45. debbie_cianciulli
    67 mos, 1 wk ago

    Kevin that's one of the funniest things I have read in a while……never try and change someone…..

  46. debbie_cianciulli
    67 mos, 1 wk ago

    hahaha….that is mad funny…..never try to change a person…

  47. 67 mos, 1 wk ago

    Thanks…..just a silly story.

  48. 67 mos, 1 wk ago

    Yep.

  49. debbie_cianciulli
    67 mos, 1 wk ago

    I dont know what happened there with that comment twice, the first time my comp. stated it didn't go through then blam on there twice my computer at work is terrible……

  50. debbie_cianciulli
    67 mos, 1 wk ago

    I dont know what happened there with that comment twice, the first time my comp. stated it didn't go through then blam on there twice my computer at work is terrible……

  51. 63 mos, 3 wks ago

    Exactly!!!

  52. 63 mos, 3 wks ago

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

  53. 63 mos, 3 wks ago

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

  54. 60 mos, 2 wks ago

    Ha! Not laughing “with” me?

  55. 60 mos, 2 wks ago

    Exactly, Alisa!

  56. 60 mos, 2 wks ago

    Oh no! The family portrait!!!

  57. 52 mos ago

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

  58. V
    52 mos ago

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

  59. 51 mos, 3 wks ago

    Get out while you can!!!!!!

  60. 51 mos, 3 wks ago

    It is crazy. Never again!

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