Dear Guy

Guy is a single 41-year-old Manhattan man who has had several successful long-term relationships. Readers may send him their questions at DearGuy@Observer.com.

Dear Guy,

I am a 34-year-old professional woman. I have always considered myself to be smart, hard-working and ambitious—qualities I’ve never felt I should have to apologize for. Unfortunately, because of the way I look (I’m half-Japanese, half-Dutch), I seem to attract a certain kind of man. On paper, they’re all exactly whom I would choose as a mate and father to my future children: driven, Ivy-educated and clean-cut. But I find that once I start dating them, they all seem to want me to be little more than arm candy. The last man was always asking me to wear backless dresses to his various functions, and then would stick me in the corner with the other girlfriends/wives and ignore me. I met Joel at a liquor store in Nolita a month ago. He’s 28, shorter than most guys I’ve dated, with an auburn beard. Even though he’s covered with tattoos, he made me laugh within minutes of meeting him. He’s different than anyone I’ve ever been with and makes me feel wonderful. Our main problem is how different our lifestyles are: He lives with five other people in a warehouse in Bushwick—I’ve lived alone since business school, and am saving to buy my apartment. Joel is a struggling—but brilliant—musician who hasn’t had a real job in a while and, truth be told, smokes a fair amount of pot. I don’t care how much money he makes, but I do care about the waking up in an apartment full of guys where every available surface is used as an ashtray! Anyway, Joel says I should try relaxing a bit more, that he’s happy with the way his life is. But I just know that it must bother him on some unconscious level that I make so much more money than he does. I think that if he just applied himself and found a job he really cared about, he would feel better about himself in general, and together we could afford a great apartment. I’ve started to make a few secret phone calls on his behalf. Should I tell him?

—Baffled in Battery Park City

Dear Baffled,

You’re crazy!

Sincerely,

Guy

Dear Guy,

What’s with all the men in this city? I’m a sexy 39-year-old woman looking for love. I go to the gym six days a week, can cook a gourmet meal, knit, speak four languages, have traveled in the Far East and went to Penn. You’d think that I’d have no problem, right? Wrong! I’ve been on Nerve, Match, JDate, The Right Stuff, EHarmony and even placed an ad in the back of The New York Review of Books and … nothing. Every man I’ve met has been a balding mouth-breather with a secret f-ck-buddy and mommy issues. I’ve had it! A friend told me that she knew a friend who moved out to Montana and within days met a handsome man who owns his own ranch and is about to separate from his wife as soon as he works out the details. I’m preparing to move there and try my luck. What do you think?

—Utterly Frustrated in
Fort Greene

Dear Utterly Frustrated,

You’re crazy!

Sincerely,

Guy

Dear Guy,

I never thought I’d be the kind of woman who would still be single at 34 (let alone writing to an advice column!). But here I am. I met Dave at a friend’s dinner party six months ago. We hit it off and agreed on everything from favorite movie (Philadelphia Story) to best Chinese food in the city (that hole-in-the-wall on Allen Street). Dave was unlike any other guy I’ve ever met in New York—ready to settle down and seemingly hard-wired for domestication. But that’s the thing …. All he seems to want to talk about now is having kids. By our second month together he was joking around about whether or not our hypothetical kids would inherit my terrible singing voice. At first I was impressed he was able to talk about such things—most men in this city would rather hit themselves in the face with a rake. But after a little while, it just started seeming weird. He has already bought three stuffed animals “as a goof,” he says. He also keeps mentioning statistics of “high-risk pregnancies after 35”—and we’re not even living together! But I wonder if I’ve been alone so long that I just can’t recognize a great man when I find one. Please help me get over my resistance!

—Feeling Fertile on Myrtle

Dear Feeling Fertile,

You’re crazy!

Sincerely,

Guy