12/08/2008 05:12 am ET Updated May 25, 2011

Little Boy Blue

"Jamie, can we take you shopping for jeans?"

Tiffany said those words to me last Friday night, prior to a Halloween party. She was speaking for her and KC. This was not the first time a woman had asked that question, so I immediately knew what these ladies were talking about: my "fat jeans."


In February, my girlfriend at the time -- Ms. February, some of my pals call her, since we dated exclusively for those 28 days -- asked to take me shopping for jeans. She said all the right things, "The new style will show off your ass," etc, but I didn't take her up on her offer.

See, I'm a JT -- Jeans Traditionalist. I like 'em faded and comfy. Life used to be so easy: Gap or Levi. What investments! Those jeans outlasted senatorial terms. Those jeans worked for everything: Skybar and Skid Row, Homecoming and Habitat for Humanity.

A few years ago, the style switched to dark jeans. I balked. Until I realized my attachment to faded blue was costing me an attachment to bleached blondes. While I may be a JT, I'm also an HG (Horny Guy). The latter takes precedence. The ladies liked dark jeans, so that's what I bought.

This switch to the Dark Side highlights an important difference between the sexes. If a guy buys his significant other a bottle of perfume, but she doesn't like the fragrance... she is maybe wearing it on his birthday. Conversely, if a woman gives her man new cologne, but he doesn't like the aroma... that dude is bathing in it every day.

Fortunately, I found a way to rationalize the selling of my soul; faded or dark, I was still buying Gap and Levi's, right?

But the fashionistas weren't finished. Oh, no, they couldn't stop with just dark denim. Now, women like 'em tight, too. Excuse me, "skinny."

I do not know what man signed off on this, but he should be hung from a changing room clothes rack with a pair of True Religion. Let's see him find God then.

But what can I do? I'm a pale, bald guy chasing women above my pay-grade and security clearance. In this era of "Change," I had to change.

So I emailed Tiffany and KC.

OK, ladies. I may go shopping today. Macy's is having a big sale.

What brand of jean should I be looking for? Please keep in mind that I am not going to pay a lot of $$. (Of course, the earlier Macy's reference probably clued you into that!)

This was Tiffany's response:

I think you want a dark wash skinnier leg. And you want some bleaching that draws the eye to the package/crotch area.

Hmmm. So much for "eyes" and "sense of humor" being most important.

KC added to Tiff's advice:

It's called "whiskering", but don't tell the sales girl that; she'll try to set you up and not with a girl.

Whiskering. Seriously? I did not need to know that term.

Sad to report, I went to the mall yesterday.

I had some things to return to the Gap, so I stopped in there first. They were having a sale, which is never good for me. The Gap is like Target; I'll never just run in, grab the one thing I need, and get out.

Once I located the men's side of the store -- Am I crazy, or do they switch it, like, every other week? -- I found two pair of dark jeans. Different denims; one whiskered, one...shaven? (Ewww) Most importantly, both skinny.

Trying on the first pair nearly required a helper. How women do this everyday, I have no idea. Eventually I worked the jeans up my legs. But they wouldn't go past my hips. It took a while, but I finally realized they aren't supposed to go above my hips. The label said: "Waist: Low". Am I shopping in the f'ing Castro? I sat down on the bench. My boxers popped over the belt loop like a Jack-in-the-Box. Next!

The other pair took slightly less time to don. But I just didn't feel comfortable, which, as I recall, is the best part of wearing jeans. I picked up my fat jeans and looked at the inside tag. "Relaxed Fit." Ah ha. Now I know why they seem so baggy. These new jeans say, "Reticulated Python Fit".

In serious need of a second opinion, I hesitated to ask the sales woman. I mean, what if this turned into a "shoe store" thing? Remember when you were a kid and your mom would press down on the front of the shoe, asking, "Is this your toe? No? Oh, good. You'll have some room to grow into them." I really, really didn't want the Gap Girl going, "Is this your junk? No? Oh, good. You'll have some room..."

Despite the lack of blood flow to my feet, I decided to buy both pair. I figured they'd look better once I got them home. Say what? Never in the history of man has that reasoning worked. It doesn't work around closing time at a bar, so why would it work at 3:00 PM in a mall?

The jeans are going back to The Gap today. But I'm not giving up on the dark and skinny. I will exchange them for two of their bigger brothers.

Now, how to get Tiffany and KC into the changing room with me...