Is Dating Your Best Friend a Good Idea?

Did "When Harry Met Sally" Have it Right?

Dear lovelies:

Ah, the weekend! Being away was so good! We hiked; we swam in the Hudson River at a private swimming spot; we made fires; we sat in the hot tub and looked out at the nature preserve the house we'd rented was on. We drove underneath a small bridge and then trekked through the trees around it to reach a waterfall, where we hopped into the water and put our heads under the rapids. We went to a few yard sales (and I got some amazing stuff). We had cook-outs on the grill, made fires and roasted marshmallows, watched movies before bed. We listened to Sam Cooke, Patsy Cline and Department of Eagles (along with a mix that Arlo Pumpernickel made me for the trip). It was a gorgeous, idyllic, relaxing weekend--and the company was hard to beat. (Kermie Ottawa was there, among others, with his incredibly sweet new-ish girlfriend, a yoga teacher and massage therapist; as soon as she heard about names like Sir Hugo and Sean O'Shaughnessey--not to mention Arlo Pumpernickel--she wanted a pseudonym of her own.)

Among the attendees was good ol' Jake Stein. Those of you who have been reading the blog from the get-go might recall that Jake and I were best of friends for a year (while we were living in D.C.) ... and then we tried to date each other for a while, which wasn't such a great idea. Luckily, though, we were able to go back to being friends again afterwards.

Jake is hilariously funny, whip-smart and incredibly sweet. He's a guy's guy--he loves to drink beer and watch soccer games; to go to rock concerts and play pick-up football; to attend bachelor parties and stay out late at parties. But he's also a girl's guy, in the sense that he has a lot of patience for talk about the vagaries of love and relationships; he's a compassionate and careful listener, who's also perfectly good at offering up good, juicy stories from his own life; and he even likes to read the Weddings section of The New York Times!

All weekend, he had us cracking up constantly. For instance, at one point, when I first appeared before the group in my new Baywatch-red bathing suit, I said, "Is it just me, or do I look kind of Baywatch in this get-up?" Without missing a beat, Jake said, "Right color. Wrong tits." (I'm not exactly well-endowed in the breast-al area.)

I wish I could better describe Jake's hilarity, for the sake of your giggling enjoyment ... but for the moment, I hope it will suffice to say that once he gets me laughing, it's often days before I stop.

Jake just got engaged to a wonderful person (although his fiancee wasn't able to make the weekend away with us, because she was spending the weekend with her mother and sister). The romance unfolded perfectly naturally: They hit it off right away, quickly became exclusive, and moved in together before a year had passed. The engagement came shortly afterwards--and he seems so happy and contented with the relationship. Over the weekend, Jake was saying, "It's always just so smooth and easy with her. We never fight." I am confident that the two of them are the loves of each other's lives.

When Jake and were dating, on the other hand, things were not so easy. We didn't really fight, but there was a lot of tension--and maybe part of the pressure was my conviction that if things didn't work out between us, it would be a sure sign that I was inherently unloveable ...

Anyway, more about all this tomorrow--when I'll also (continue to) discuss the related question of chemistry. That strange, strange thing.