Hi Doc, I wonder if you can write on the topic of getting over women’s sexual histories, especially when they’ve gone through long hook-up/casual dating periods and a man has not. Or maybe about guys who’re plagued by feelings of not measuring up in experience, number of partners, degrees of wildness, etc. I think many of your readers will be going through this as well, dealing with feelings of insecurity and perhaps craving some of the wild things or numbers of partners they hear of friends doing, hear of their dates or girlfriends doing, but none of which has ever been extended to them.

Obviously this is largely a personal request–I had a potential partner I was interested in tell me she’s been through a hook-up phase, had threesomes with previous boyfriends, but wouldn’t be doing any of that again. I didn’t press her on it, but it killed me to hear that, immediately and irrationally made me feel it’s about me. It made me feel like I’m not interesting or cool enough or exciting enough for her to be a bit wild with me, now that she’s had here YOLO moments. I think I’m really, maybe obsessively, struggling with thoughts of the ease with which many women can go wild if they so choose (I know that’s not the case for every or even most women, but it seems the case for those I’m attracted to). I am craving some wild experiences myself, if only so I no longer feel threatened by women who have had them and can graduate from feeling upset when I hear or suspect a woman I am interested in partook of orgies or something. For what it’s worth, I live in a major city where this kind of stuff is anecdotally not uncommon. Maybe I should be reading guides to make it happen for myself rather than tell myself I need to suppress these desires, though they are probably born of YOLO/FOMO, New York Times articles about orgies in NYC, porn, and a desire to make up for my entire 20s spent in depression despite having everything seemingly going for me.

Whatever thoughts you might share or write would be greatly appreciated.

Missing Out

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