T-Shirts to Tutus!

My girlfriend is a wonder. She's loving, smart, sensitive, athletic, sweet, has amazingly warm hands, and our bodies fit together when spooning like they were tailor-made. There's only one problem: She dresses like a boy!

There's nothing wrong with being comfortable. We both have jobs that don't demand that we show up in any more than a T-shirt and jeans. But when we go out, I think she'd be so freakin' hot if she put on something that didn't look like she's about to do yard work!

All of my female friends are somewhat stylish, as are most of the women I've dated previously. I'm no metrosexual, but I do pay attention to these things, even though I can't afford to be in the latest and greatest myself. Heck, I wouldn't ask her to do anything I wouldn't, so I'm going to be investing in some new duds as well.

My girlfriend is aware that clothes do matter, having been mistaken for a lesbian several times. And I think she's ready for a change . . . heck, we both are! Any advice?

Don't Wanna Date a Boy

Do not, under any circumstances, mention your ultra-femmy, glamour-girl exes to your current girlfriend. (Note that I skipped my normally knee-slapping introductory sentence in order to bring you this imperative piece of information immediately—that's how crucial it is!) Nothing—and I mean nothing—enrages a woman like being compared unfavorably to paramours past. I mean it. Do not test this theory or you will regret it. Got it? Excellent.

I've had several dozen sartorially challenged boyfriends and have found that the only sure-fire way to get them to dress better is to buy them new clothing. But that gets expensive and men are easier to manipulate than women anyway. Most (not all!) of you will choose outfits solely based on what smells the least foul and has the fewest ketchup stains.

I had one boyfriend who was convinced that fanny packs were the height of fashion and wore his constantly. This guy also rocked a rat tail and pleated trousers, but it was the black nylon sack strapped to his waist like a pen-and-wallet-filled colostomy bag that skeeved me the most. I tried every trick in the book to get him to give it up, but my pleading fell on obstinate ears. He flaunted it proudly until a very mean queen he worked with marched up to him, raised one eyebrow, and barked "Honey, the last thing you need is more hips." It was never seen again.

But I digress. As I mentioned, changing a woman's style is a far trickier matter. Begin with copious compliments. Tell her how hot you think she is and how you wish she'd wear clothes that show off her ass/legs/belly/body-part-of-choice. Then suck it up and go shopping with her. Lucky for you, she sounds like the kind of girl who looks at shopping as a chore, so maybe you can get away with doing most of it online.

Start off slow with a simple skirt and fitted T-shirt combo. She'll probably feel kind of uncomfortable at first, so immediately drop to your knees and go down on her. Once she notes how quickly and easily accessible her girl parts are in a skirt (as compared to clunky button flies or overalls), she'll start to think twice about her predilection for pants.

Once you've got her used to going sans slacks, work your way slowly up to a more revealing blouse and pair it with a slightly shorter skirt. Perhaps you should make this outfit a gift. Take a female friend (not an ex-girlfriend) shopping with you and buy whatever she tells you to. Including racy—yet still tasteful— underwear. Wrap it up and present. As she opens the gift, throw her down on the bed and once again go diving for pearls.

You see what I'm getting at here: positive reinforcement. Too many people dole out compliments like they would vital organs. So don't be stingy with the "you're prettys." Like flattery, fancy chocolates, pink peonies, and expensive champagne, there's no such thing as too much cunnilingus. She has to see that you not only think and say she looks hot when she dresses up all girlie, but that you are willing to use your oral skills to drive the point home.

Dos and don'ts? Write Dategirl at dategirl@seattleweekly.com or c/o Seattle Weekly, 1008 Western Ave., Ste. 300, Seattle, WA 98104.

 
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