I just got this Facebook message, so I thought I’d share my “enlightened wisdom” with all of you.

“Cathy, I need your enlightened wisdom. I’m dating a wonderful woman that I am quickly falling in love with. My problem is that, while I love how liberated and wild she is, I sometimes feel really icky when I learn things about her past. I feel stupid for feeling icky, b/c part of what makes us so compatible is our amazing, taboo-busting sexual creativity. We do stuff together I’d never feel comfortable doing with someone else, and it doesn’t make any sense for me to feel jealous of things she did before she met me. But I can’t help feeling icky and sometimes I can’t stop thinking about it. I’m completely secure in our monogomish relationship (like, I have no trust issues at all). It’s just images in my mind that kind of haunt me sometimes, and I wish I could get over them because intellectually they don’t bother me at all. They bother my cave-man sensibilities. But I’m intellectually bothered with my cave-man self for being bothered. You write a lot about polyamory and jealousy and relationships, so I thought I’d get your take. Hope everything’s going well!”

While reading this I flashed back to 26 or 27-year-old me, showering with my live-in boyfriend, post-divorce, newish to D.C. Trendsetters that we are, we were discussing butt stuff three or four years before it became mainstream.

You guys, I got really upset that he’d done butt stuff without me. Like, sick to my stomach. I wasn’t judging him, I mean maybe I was a little. But I was mostly jealous. Jealous of a girl I’d never met, who posed zero threat to me, for taking his butt stuff virginity. I felt like a noob, and at the same time felt cheated. I was straight out of Alabama and I had hella boxes to check off and I wanted to check them off with someone who was also exploring. Not with someone who’d been there, done that, and bought the tee shirt. I worried he’d compare me to her, judge me less proficient at ass play.

That’s why I can’t help but laugh at men who go on about how they won’t have sex with women who have had sex before. Dude, your insecurity is showing.

Totally separate from sex, there’s an impulse to avoid being obviously bad at things. There’s a whole TED talk about it. But of course it applies to sex as well.

There’s also the impulse to equate scarcity with value and novelty with meaning. We consider “firsts” more significant because firsts tend to be more memorable. No one wants to feel like just another asshole (literally and figuratively). We all want to feel like special snowflakes.

Here’s another economic reality for you — Life requires tradeoffs. I’m not here to tell you what to value. But I am here to tell you that if you value experience, adventurousness, and open-mindedness, you’re going to have to let go of the idea of being someone’s first on a lot of stuff.

That doesn’t mean you have to love it. Being someone’s first DOES feel special. Knowing someone has no one to compare you to DOES feel more comfortable. But letting go of the fairytale of a life without tradeoffs is an essential part of growing up.

One tip for moving beyond the “ick” feeling is to eroticize the images. Practice listening to her talk about past experiences with the goal of getting turned on. I did it with my ex and learned how to get aroused by thinking about him with other women. Compersion has become one of my favorite parts of non-monogamy. It’s a free source of erotica in which I know and love the characters!

Whatever you do, forgive yourself for feeling threatened. It’s totally normal and natural. But I’d recommend that instead of denying the feeling or running away from it, that you lean into it and turn it into something good.

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