Look who's caulking
My girlfriend of four months and I work in the same warehouse, and aren't required to dress up on the job. Although she's very attractive, she wears jeans everywhere: Levis to work, Levis cut-offs to swim, etc. The one time I asked her to dress up for a date, she wore a jean skirt. Am I far enough into this relationship to buy her an outfit or comment on her clothing? I don't want to hurt her feelings. We're very good together, and I can see us having a future. -- Girly Friendly
It all started in offices across America with "casual Friday." Like horror-movie ooze, Gap khaki spread across the work week, until casual Friday was preceded by casual Monday through Thursday. There was no place to go but down. Before long, casual Friday started looking more like sloppy Saturday, and your corporate lawyer was greeting you at the elevator in flip-flops and pajama bottoms.
Lately, it's increasingly hard to tell $20 million leading ladies from those earning $20 a day redeeming cans, and ragged, unshaven Hollywood moguls from ragged, unshaven Hollywood Boulevard bums. Since both often appear to be shouting at nobody in particular, it helps to look for the Bluetooth headset -- a sign that the guy probably has a real live person on the other end of his ravings, and parks something tagged "Jaguar" or "Mercedes," not "Please Return This Cart To Staples."
Back on warehouse row, you don't expect your girlfriend to spend her days pallet-hopping in a Roberto Cavalli evening dress and four-inch Marabou Mules. But, assuming you won't be transporting her to dinner on a forklift, you aren't out of line to want her to dress for dates as if she's aspiring to change your life, not your oil. Instead of despairing that she has yet to break the denim barrier, try to see the fact that she worked her way up to a jean skirt for what it is: a riveted, five-pocket ray of hope. Her effort suggests she isn't willfully ignoring what you want. She's simply ignorant of the obvious: You attract more men with lace than burlap.
The best way to tell somebody, "Here's how I'll find you attractive," is not to suggest that you have, for some time, been finding them not-so-attractive. Tell your girlfriend you're taking her someplace elegant, and want to buy her something special to wear, then make helping her pick it out part one of your date. Wax on about how beautiful she looks, and keep waxing after she's back in her barn-wear. Window-shop at establishments that do not feature denim, pointing out how hot she'd look in this or that. You get the drill. And she'll get the message, and without you ever saying you've kind of had it with greeting her at the door and wondering, "Do we have a date or a broken water main?"
Tempting as it may be to shrug off fashion intransigence as a petty idiosyncrasy, if you need eye candy to be happy, you two won't make it unless she starts dressing to the nines instead of the threes. Whether she can or will remains to be seen. While you're waiting to find out, try to incorporate her current look into your fantasies -- not the way it makes you picture her cleaning out the garage, but by fast-forwarding to the end of the day, when the jeans come off. A little overtime in the imagination department might be what it takes to have a future with this girl -- especially if she intends to start it off in a relaxed-fit, button-fly wedding gown.
Mash flow issues
I'm 40, the cute girl from upstairs is 23. When she stopped by to commiserate about loud neighbors, we had a beer, went dancing and then had sex. Afterward, she seemed weird and left abruptly. I wrote her a note, "Sorry if I made you uncomfortable, but I love you and look forward to seeing you again." She hasn't looked at me since. Where did I go wrong? -- Mr. Neighbor
Grateful as you may be to a girl for having sex with you, it's never a good idea to let on. You could've had a future with her -- the kind 40-year-old guys without handfuls of bling typically have with 23-year-old girls: jump-starting their cars, lugging their couches up four flights of stairs and maybe catching a little action when there are no hot young guys to be found. You blew it, though, with "I'm a lonely sack of emptiness!" -- which is how "I love you" translates after one beer, one dance and one roll in the sack. (You say, "I love you"; she says, "It seemed like a good idea at the time.")