The Hating Is The Hardest Part

I wrote you two months ago about a male co-worker who was flirting but never asking me out. You said to flirt with him, but date others. He's still flirting, and watches me like a hawk, but that's it. Yesterday, he overheard me talking about some date I had. Apparently, his face went beet red and he got all "weird." He didn't even come say goodbye before leaving, as he always does. I really like this guy -- he's such a sweetheart -- but I'm getting frustrated. Should I turn on more charm? Or even just ask him out?

--Still Interested

There are those things that are really hard to say: "I'm leaving you for your best friend." "A few lawyers might be dropping by about some downloads I made from your computer." And "You should probably get tested for Hepatitis C." And then there's "Hey, wanna grab a drink after work?" A guy who can't squeeze those last words out, especially to a girl who's been flirting with him for months, doesn't need to be charmed, he needs prosthetic testicles. But, wait! You've got a pair in your purse! You bring them out as needed, say, when the car mechanic tells you he has to put in new belts, and they have to be Gucci, imported overnight from Italy, only $500 a piece (he's giving you a break). That's when you slap your brassies on the counter and tell him how it's gonna be. Take charge. Just like you're tempted to do with the co-worker whose male role models are clearly less Navy SEAL than baby seal. So, should you ask the poor dear out? Grab his sweaty little hand and yank him over the hump? Surely he's got masculinity in there somewhere, like a zit that just needs to be popped. You'll be the guy for the first 20 seconds, and he can take over from there! Sorry, but if that's what you're thinking, it's probably because you're mistaking this guy's festering weirdness for shyness. Shy men have a tough time asking women out, but ultimately, they're men, and if they're into you enough, they'll find a way, even if they have to suck down so much powdered elk antler that they're likely to paw and snort a little if you say yes. This guy sounds like the type that therapist Robert A. Glover describes in No More Mr. Nice Guy -- a guy who's not nice at all, but is filled with "toxic shame," and is so desperate for approval, especially from women, that he hides who he is and never asks for what he wants. Not surprisingly, he doesn't get a lot of dates, and tends to be filled with repressed rage and hatred for women. Glover told me that, in a relationship, this passive guy often turns passive-aggressive: He's chronically late and "forgetful," puts the woman down in public, and he's generally passively manipulative "because he never gets his way -- even though he's never asked for it." Assuming you weren't flirting with great subtlety, like from the women's bathroom with the door closed and the hand dryer on, you should consider the guy a lost cause. Of course, it's got to be tempting to gather the girls for an afternoon of Chardonnay and analysis: Maybe Glover's explanation fits, maybe the guy wasn't breast-fed, or maybe he was -- until he was 8. Pondering what's wrong with the guy can be a productive endeavor....well, compared to continuing to turn on the charm to see if it'll eventually cause the guy's head to explode.