Reality Check for a “Messy” Friend

Dear Dategirl,My friend "Joan" is in her late 40s, though she looks years younger and lies about her age. She works out constantly, has had some very good work done, and dresses well—so she's rarely called on it. Unfortunately, despite her beauty and bubbly personality, she's always had bad luck with men.I've always felt this is because Joan will only date model-handsome men, and refuses to consider anyone over 40. Right now she's with some young stud she met online. They started off hot and heavy until she found out he was still married to the wife he'd claimed he'd divorced after she got too fat. He and the "fat wife" eventually did get divorced, according to Joan, so they're back on. But he's already cheated on Joan twice, and lives rent-free in her condo.I'm trying to like him, so the other night my husband and I met the two of them for drinks. The bartender hadn't even taken our order when Joan announced that they were trying to get pregnant! I don't know how old the boyfriend is—early 30s?—but there's no way Joan can possibly carry a baby to term; she's almost 50! I'm afraid my friend has really lost her freakin' mind. I feel like I should talk to her, but what to say?—Am I an Enabler?

Everyone has a messy friend or two. The fun-haver who's always locking herself out of her apartment and ringing your doorbell at 3 a.m., or the drama queen whose collection of lovers and sworn enemies rivals All My Children's Erica Kane.Joan is your messy friend.Once you accept this, perhaps you'll be a little more patient with her. I've always felt that aging is much harder on women who've relied heavily on their looks. (Luckily, I've always been able to count on my staggering intellect.) My most beautiful pals have always had the roughest time with birthdays that end in zero. And sure, I will admit a certain unflattering sense of satisfaction that comes with witnessing the fallout.So Joan may pass for a lady in her 30s now, but how long do you think she can keep that up? This weird pregnancy twist makes it sound as if things are getting desperate. Getting involved with a much younger man who dumped his wife when she got fat? The pressure to stay perfect as her body is betraying her must be overwhelming.The problem with messy friends is that they aren't generally fans of the reality check. I know, because I've been that messy friend. I recall one instance in particular when a pal finally snapped and told me that a certain Swiss cartoonist had no intention of leaving his girlfriend—and Paris—to return to me. Did I take her advice and move on? Why, yes, I did—from my friendship with her.So sure, talk to her, but what will you say? "Joan, you do realize your ova are basically desiccated raisins, and the chances of you conceiving are about as good as the chances of you winning the next cycle of America's Next Top Model?" Even if you're tactful, she's probably not going to want to hear this.I think you need to be realistic about your friendship with Joan. She probably has a ton of great qualities, but she seems to have a tenuous grasp on reality. I highly doubt she'll welcome a visit from the Downer Squad. And besides—did she ask for your opinion? Nope. Doesn't sound like it. That's because I'm sure she already knows what you

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