Q: I'm 32 and engaged to a great woman who is 29. Despite being younger, she has vastly more experience in the sex department, while I have been with only a handful of other women. To balance the scale a little, she has stated that it would be fine for me to have one last fling before our wedding, no questions asked. I appreciate the gesture, and I think I would be a fool not to take advantage of it. But how much information do I have to disclose to both my fiancée and the other woman? I don't think my fiancée wants to know the details, but it still feels dishonest not to share them with her. She doesn't want our friends or family to know about it, so this other woman would have to be a total stranger. Am I even obligated to tell a one-night stand that I'm engaged and my fiancée told me to have one last fling?
A: Those who have never engaged in impassioned conversation with me probably don't know that I have a minor speech impediment. When I'm trying to make a very important point, I stammer a little. More Joe Biden than Porky Pig, I can't seem to get the words out fast enough and I end up mushing them all together on the first try before getting it right. To you, sir, I say, "Bu-ma-sh-ma-wha?!"
If your idea of happily ever after includes the woman of your dreams banging you and only you for the rest of your lives, then don't marry this woman. At least not yet, until you have had a more serious conversation about your beliefs on monogamy. She's not batting an eye at the thought of you having sex with another woman of your choosing. She either has a disconnect between sex and love, or she's allowing you this fling because she feels it permits her to get some side action in the future. The reason she gave for letting you sleep with someone else is not a real reason. There's no score to even when it comes to the sexual histories of two people about to get married; you simply accept the other person and all the baggage they bring along. You can't see beyond the image of burying your balls into some random hottie, so you've eagerly agreed to your fiancée's proposition without questioning motives or repercussions. Meanwhile, you're feeding your own insecurity about her past. This is all very unhealthy.
"But Alexis," you might say, "I thought you were an advocate of open relationships." That is true; having sex is a basic human function that just has to happen sometimes, like eating when you're hungry or sleeping in when you're hungover. It doesn't have to be any more meaningful than that Cheesy Gordita Crunch you ate last night in desperation. However, open relationships aren't for every couple. You have to create and nurture an emotional bond first, then establish mutually agreed-upon conditions under which it's OK to nail other people. Her willingness to let you have sex with someone else may seem like honesty and trust to you, but it could also indicate that she believes what you don't know can't hurt you. We all know that if no one sees you stuffing Taco Bell in your face in the corner of a dark parking lot, it didn't happen. A lot of people also feel this way about sex, regardless of their partners' beliefs.
Your fiancée is more interested in protecting her secrets than protecting your relationship, and you have hangups about the notches in her bedpost. You both must go back to the monogamy drawing board before getting married. You're coming from two very different places on the matter, and I advise against taking the plunge until you're both completely honest about why you're even having this discussion.