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Is Dating Your Best Friend a Good Idea?

Is Dating Your Best Friend a Good Idea?


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 I 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.



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