Anal Sex On A First Date

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Drew Barrymore and Adam Sandler star in Columbia Pictures romantic comedy "50 First Dates." (DARREN MICHAELS / Associated Press)
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Ask Anna is a sex column. Because of the nature of the topic, some columns contain language some readers may find graphic.
Is anal sex appropriate on the first date or should I just hold off for a few more dates, or just forget the hole thing? —Really Confused
I’m really amused by your “hole” typo, especially in regard to anal sex. Should you, indeed, forget the hole thing? Let’s get to the bottom of this (sorry).
First, what do you mean by “appropriate”? I’m guessing you’re wondering if such an ask is “suitable or proper” as defined by social or cultural norms. And the answer is: It depends.
Is the date in question a gay man, for instance? Is it more socially acceptable for gay men to have sex on first dates? Yes. That doesn’t mean they all want to, but the odds are more in your favor that you would get a yes than if you went on a date with, say, a straight ascetic monk.
If the date in question is a woman who likes men and you are a man and you have been flirting heavily prior to this date and she has enthusiastically mentioned how hot it would be to get canned in the can, then I would also say the odds are in your favor.
If, however, you have zero input as to the sexual preferences and proclivities of your lady date and you spring this question on her over a Bloomin’ Onion at Outback Steakhouse without context or foreplay or any regard for her sexual desires, then, no, you’re probably not going to receive a favorable response.
Context is everything, RC. Are you doing the work prior to this first date to ensure her maximum safety and enjoyment and trust? Are you expressing your desires to each other and finding where they might overlap?
But Anna, if I don’t know anything about my date can I still ask for butt sex?! I hear you whisper-screaming. You can ask for anything you want, RC. You can ask to be called Ronald McDonald and spanked with a gilded shovel, but that doesn’t mean you’ll get it.
I will say that your desire for anal on a first date is very much at odds with American sexual mores. For one, anal sex is still considered pretty taboo, though a study from a few years ago in the Journal of Sexual Medicine did note that 45 percent of women in their late 20s had tried anal sex at least once. That’s more than 0 percent! But it’s not 100 percent, and even if it was, it doesn’t mean these women want to do anal again or with you or on a first date.
And then, even if you do find an anal-lovin’ gal, there is another hurdle to overcome, and that is our tendency to slut-shame women who are even a little bit sexual. For instance, it’s still a stigma for a woman to sleep with a man on a first date. As long as that stigma lives, women will be less inclined to get down on a first date. Patriarchy! It ruins sex for everyone. The third hurdle is that some men don’t know how to ensure that anal sex is pleasurable for women, and, as such, women get hurt and don’t want to try it again.
As with any sexual entree, there will always be ladies out there who are fans of anal in any circumstance and with anyone, but there will also always be plenty of ladies (and men!) who are not. You could switch “anal” for literally any activity and the answer would be the same. It depends on the date and the circumstances and all the mad pathways and divisions that have made up your date’s sexual and emotional life.
Is hugging appropriate for a first date? Is kissing? Is oral? Is Outback Steakhouse? Maybe!
I would encourage you instead to ask different questions, ones that take into account the desires of others first and foremost. Such as: “What can I do to ensure you have the best first date ever?” And then do that. The more trust and care and compassion you put into your dates can only increase the odds that intimacy will follow.
Good luck, RC. May you find the hole package.
Anna Pulley is a RedEye contributor. Want to ask Anna an anonymous question about love, sex or dating? Send it below, or email redeyedating@gmail.com.



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