One question never to ask your intended: “How many women have you slept with anyway?” Chances are pretty good that you don’t want to hear the answer. No, I don’t mean to imply that your beloved is easy. There are simply too many opportunities for things to go awry.

What if her number is higher than yours? Are you going to feel insecure? Threatened because she has more “experience,” leaving you suddenly feeling inadequate? What is she hasn’t slept with very many and you have? Are you going to be worried then about what she’ll think of you?

Don’t even get started on how many men they may have slept with before they came out. Sometimes, because I like to scandalize people, I will tell someone that I can’t remember the names of all the men that I had sex with let alone how many there were. That sounds pretty bad unless I also tell you that it has been more than 20 years since I’ve had sex with a man. Then it sounds less slutty and more menopausal. You can see, though, that it could be a showstopper if I were telling a person I was considering having sex with for the first time that I can’t remember how many men I’ve had sex with!

Since I will assume we are all beyond the Puritanical presumption of whoredom if a person has slept with “too many” people ( and I recognize that it’s a leap to make that presumption), I think that part of the reason a person might ask that is to gauge their level of experience as compared to their intended.

I would like to reassure you that the number of women you have slept with is not a guarantee of skill. The best sex I have ever had was with a woman for whom I was her first. The worst sex I have ever had is with a woman who had been with far more women that I.

The first woman was kind, thoughtful, experimental and fun. She liked sex, she liked sex *with me* and wanted to try absolutely everything. Some stuff she liked, some she didn’t but she was open to the experience. She also paid attention to me and what I responded to and what I actually said I liked.

The second was so sure that she knew what she was doing that she rarely asked what I wanted and often didn’t listen when I offered up the information myself. I can remember having an argument with her because I didn’t want her to do one particular thing that she really wanted to do. Well, if she hadn’t hurt me the first couple of times, I might have been more willing. She was selfish in bed. That’s no way to be. For those of you who know my personal life, no I am not talking about That Woman. I’m not *that* tacky.

You absolutely want to have the safer sex conversation but be careful about asking The Numbers Question. Think about what it is you really want to know and ask *that* question. It’s safer that way. My theory is that if you’re not comfortable *talking* to the person, should you really be having sex with them?