[Originally published December 4, 2008.]

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I hope I didn’t wake you, Eloise. Oh, you’ve been up for hours, thinking about Jake? Let me guess: You’re watching screwball comedies and eating a pint of Chunky Monkey straight from the carton.

C’mon, Louise, whenever you have guy problems, you always watch classic movies and pig out on Ben & Jerry’s, even though your willowy frame suggests you subsist on celery and laxatives. It’s one of your charming quirks that distinguish you from the other successful, attractive women in their 30s I’m friends with who inexplicably can’t hold on to a man. That, and your career-woman-but-glamorous hairstyle that should take an hour to prepare but looks perfect straight out of bed.

I’m so glad you met me for drinks in this funky downtown watering hole that plays well-known contemporary hip-hop songs. By the way, mazel tov on your promotion at that chic company you work for, girlfriend—a round of sake on me! Boy, as a wisecracking half-Japanese, half-black Jewish woman, I love being a nonthreatening “ethnic” blend, because I get to order exotic foods and say all these trailer-worthy one-liners.

Oh, did I say “trailer”? I meant sailor-worthy. My jibes are worthy of sailors. Except I never curse!

The thing you have to remember about men, Weezie, is they want Pamela Anderson in the bedroom and June Cleaver in the kitchen. It’s in my new book, Sardonic Aphorisms About Gender Relations as Codified Through Accessible Popular-Culture References.

Another way of looking at it, which might appeal more to a hypothetical 18-to-34-year-old male overhearing our conversation on a date, is that men equate women with cars. Wait for it … And, honey, you’ve got a Range Rover engine with a Firebird chassis! I’m not even sure what that means, but I’ll dispense another one in 15 minutes.

Although we were roommates at NYU and now hang out all the time for brunch and lunch and dinner on the Upper West Side despite our insanely busy professional lives, let me barrage you with questions about your personal history while we saunter through the autumn foliage of Central Park, just so I, and anyone within earshot, can understand you better.

Since you’re being introspective, I can’t help but think about my parents’ divorce, and whether that’s responsible for making me so cynical about romantic possibil—

Whoops, I don’t know what I was thinking, talking about my problems when you’re so much more lovably flawed. Let’s get back to you, Weezie. Isn’t it nice how my casual nicknames for you authentically express our deep intimacy born of a lifelong friendship?

It seems like your defining romantic hang-up—your “hook,” so to speak—stems either from your strained relationship with your father or from the guy who humiliated you at senior prom. If you think about it, every single relationship of yours has always followed the pattern set by your father / prom date. And now it’s jeopardizing your relationship with Jake, a handsome, gentlemanly environmental lawyer from somewhere in the South who’s proven his moral worth by being super-nice to an elderly woman when you first met him. Plus, the fact that he’s still pursuing you despite your obsessive, neurotic, and, frankly, rather off-putting behavior means he must be “the one,” or maybe just a dimwitted romantic masochist. I can’t count the number of times you’ve fled wordlessly from a date with him because of an ultimately explainable thing he did that any normal person would take the time to inquire about.

Well, I hope you eventually get over your issues with your father or the prom date, in a moving and/or hilariously redemptive way, and that it coincides with your finding romantic fulfillment while someone plays a tender easy-listening song in the background.

This flea market we’re walking through while gabbing makes for such an interesting and detail-heavy scene! Do you want to buy this lamp that, as described by the sage elderly man selling it, clearly symbolizes your problems with intimacy? Oh, it’s so cute how you always flip your hair that way to convey indecision. Yes, always—remember, I’ve known you for years and, since you’re a real, three-dimensional person who actually exists, I can catalogue all your long-standing peccadilloes.

Look, there’s Jake, shooting hoops—with what looks like his best friend! They’re so cute, in their sweat-soaked gray T-shirts and weekend stubble and backward-turned local- and Southern-team baseball caps, as his jocular, vaguely Italian friend undoubtedly compares Jake’s romantic quandaries to basketball! His sports analogies are surely just as pithy and accurate as the corollaries in my book. Is he single? Hey, what if the best friend and I began a relationship that thematically informed your and Jake’s? Like, if we got together and then broke up, it might make you rethink your long-term commitment to Jake. Or, if we got married, it might make you rethink your lack of a long-term commitment to Jake. Either way, our relationship will make you contemplate yourself and Jake—and I’ll be there every step of the way, Eeze, prompting you with irrepressible quips and soul-searching questions and constantly shrinking pet names.

Yep, I’ve got a feeling everything will work out just fine for you, you effortlessly thin blonde. Well, I’m going back to my apartment now to cry myself to sleep. Coffee tomorrow?