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Ego boost required 

I am a happily married, happily nonmonogamous male. We are not wild swinger types. For us it's more about the fact that monogamy does not work than about nailing everything that walks by. Anyway, I have encountered an odd situation a few times now, and again last night, where I'll be flirting with a potential fling and she knows I'm married and she's very interested. But when she finds out my marriage is nonmonogamous, she suddenly backs out. Case in point, a coworker: We have been flirting since I started my new job a few months ago. Today she asked me what my wife would do if she found out I was sneaking around on her. Good time to make a full disclosure! But when I told her my situation, that was the end of our flirtation.

Any idea why women find the idea of cheating with me OK, but once they find out I have a free go of things, they walk?

No Figuring Women

This woman didn't find the idea of cheating with you "OK," NFW, she wanted to fuck you because you're married and presumably monogamous. Try to look at it from her perspective: When she thought you were willing to cheat on your wife to be with her, NFW, that meant you found her so attractive, so utterly irresistible, that you would break your marriage vows and risk everything to get into her pants. Sleeping with her with your wife's permission? Meh, where's the ego boost in that?

I am a 40-ish married straight woman living in New York. I have been happily married in a monogamous relationship for 11 years. My husband and I met when we were in our early 20s. After listening to all of the Savage Lovecasts together, we started to talk about the idea of "some degree of openness," as you put it.

In the past year, I have had a crush on a coworker. My husband is OK with me having something on the side with this coworker. This coworker is single (last I heard) and 17 years younger (yikes!), and he knows I am married. We had a great working relationship while we were assigned to a project together, but now he's in another department. My question is, how to go from here? After having a few good talks with my husband, I am excited about this idea and terrified. I'm having a private lunch with my coworker soon. This is fine with my husband. What can you tell me to calm me the hell down and not be so stressed? After being conditioned my whole life that monogamy is the only way to go, I am having a hard time shifting!

Newly Open Couple Lacks Understanding & Education

Have that lunch, and tell your coworker/crush that you and the husband are just beginning to explore the idea of openness. For all you know now, your much-younger coworker may not be interested in being your piece on the side. If it turns out that he is interested, take things very, very slowly and keep your husband fully informed. But even if I could relieve you of your stress and anxiety with a few words, NOCLUE, I wouldn't. You should be anxious and stressed out; it's appropriate to be anxious and stressed out. Your nervousness is prompting you to take things slowly and to be careful and conscientious about your husband's feelings. If this works out -- for you, for your coworker, for your husband -- it will be in large part thanks to the stress, NOCLUE, not despite it. Enjoy.

I have been considering becoming a woman. But the straight women I have talked to about this are very reluctant to assist me in my transition from being male to being female. I am wondering if you think that lesbians might be more open-minded in assisting me in my transition.

Gender Identity Readjustment Looming

You're considering becoming a woman -- that's wonderful, GIRL, very interesting, very compelling stuff, always a special time in a man's life. But it's not like you're rushing a sorority; current members -- the straight women you've approached, the lesbians you're thinking about approaching -- are not obligated to answer your questions, offer you assistance, host a tea, or take even the slightest interest in your transition. Find a support group for MTFs, GIRL, and you'll find plenty of women -- longtime members and new pledges -- interested in hearing about your journey. But leave the women you meet in the normal course of your life -- straight women and lesbians who are not your friends -- alone.

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