Many of us know Eleanore Wells from previous WVFC pieces on shoes, fashionable dressing for airport security screenings, and living the child-free life. We’re delighted to present her latest as a sneak preview of our upcoming month-long focus on all things love-related–physical, emotional, and otherwise–for women over 40. It all kicks off on Tuesday, February 1. Meanwhile, enjoy Eleanore’s foray into applied managerial decision making.  –Ed.

As I’m writing this, I’m a little amused that my girlfriends and I are still discussing when to have sex with a new guy. But the other night, I had a long conversation with a good friend who was near tears because the man she slept with a couple of weeks ago has not called since. Yep, at this age we’re still having this conversation.

I have this conversation quite a bit and for some reason, I’m usually the one giving the advice. I say “for some reason,” but I actually know the reason: I’ve been single all my life, am good at dating, and I feel like I’ve got this aspect of dating all figured out. There are other parts of dating life that I don’t always get—like the way men want you to need them but don’t want you to be needy—but this one I do. So I’m going to take this opportunity to share with the many single women out there what I know about how to make the decision to roll around naked with the New Guy for the first time.

That’s right. A decision tree, for this not-usually-rational decision. When you have to make an important decision at work, you generally think about it ahead of time and seriously weigh the different outcomes. You don’t decide at the last minute. This decision should be no different.

Here’s a scenario. You’re at a bar/party/conference/car wash/restaurant…wherever. You and “Scott” strike up a conversation and seem to hit it off. There’s lots of laughing, flirting, and witty conversation. At some point it becomes clear to both of you that you may want to dial things up a bit, either right now or very soon.

The “sex too soon” thing is something that only women grapple with. I’ve never heard a guy wonder how “when to have sex” will impact the relationship-that-is-yet-to-be. But the world’s not fair—we already know that. Follow my advice, though, and it should help you avoid getting your feelings hurt.

The thought process is not a straight line, though. It’s more of a schematic. So pay attention, and be honest with yourself.

The first thing to ask yourself is: “What do I want from this guy?” (Caution: if you’re feeling really lonely, you probably should skip this exercise completely. Sex-because-you’re-lonely will probably make you feel even lonelier afterwards).

Once you decide what you want, you can decide your next course of action. Just click on the chart below to bring it up to full readable size.

Click to enlarge.

This is by no means foolproof. But I think it’s a pretty reasonable facsimile of the way things shake out much of the time. Go ahead and do your thing . . . and let me know if it works for you.

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  • Dr Pat Allen January 30, 2011 at 9:35 pm

    Dear Maggie,

    I do love good students! Men will appreciate the insistence that condoms be used if they are evaluating a woman as a longer term partner. “I never have intercourse unless a condom is used” means never and it isn’t personal. And, it means that the woman who is prepared with condoms and a calm request will be recognized as a woman who is careful and certain about her right to remain free of sexually transmitted diseases. Ergo, less likely to give the guy some disease. Trust me. This could be a revolution.

  • Maggie G January 30, 2011 at 7:07 am

    Very good analysis. As Dr. Allen would say, condoms should be a recommended action in all the scenarios.

  • eleanore wells January 28, 2011 at 9:17 am

    @Roz: Hey, don’t throw it in a drawer. Test-driving this could be your “excuse” for getting back in the game! Let us know how it worked…


  • Ted Cohen January 26, 2011 at 6:01 pm

    I had more fun – and learned more – reading Eleanore’s primer on dating than I’ve had on most dates! This should be required reading for everybody, whether they’re “in the fray” or not.

  • Elizabeth W January 26, 2011 at 1:59 pm

    On a personal level this was a well timed find, let us just say.
    I’ll be sharing this with friends, and definitely keeping the chart in my arsenal… for a chuckle as well as for excellent guidance.

  • Anonymous January 26, 2011 at 11:06 am

    Eleanore, the consummate sex strategist, is spot on. The fact that she views the world as one in which women are calling the plays is the best part. I am going to remember this should I reenter the fray.

  • roz warren January 26, 2011 at 10:17 am

    I’m definitely going to print this one out and throw it in a drawer to refer back to if I ever start dating again.