Ink Pen by Phil Dunlap for October 23, 2010

If you start out trying to be friends with a woman and then fall for her romantically, it ends badly (unless she likewise falls for you, in which case you might as well give it a shot). Similarly, if you start out romantically inclined towards a woman but you try to win her by being her friend, it also ends badly. If you’re “interested” in her, let her know it up front, because if she assigns you to the “friend” category that’s where you’re likely to stay, however much you wish it were otherwise (and no matter how many Rom-Coms end up differently). I’ve known some couples who would now be called “friends-with-benefits” (although I prefer the term “F- - - Buddies”), and it seems to work for them, but that can potentially go down in flames if one or the other party ends up in an outside, serious relationship…

My best friend for the last ten years was my girlfriend fifteen years ago. We’ve been through a lot together (and been there for each other when we went through hard times separately), and if I ever get married she’s going to be my “Best Man.” Of course, she’s bisexual, and one of the things we have in common is our taste in women. So far we’ve never been faced with the prospect of competing with each other for one (and I don’t think either of us could handle sharing one), but that just may be luck…