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Lesbian 101: Rules for a One-Night Stand

by | Apr 24, 2008 | Dating & Relationships, Our Lives, Uncategorized | 5 comments

Today, we’re going to discuss one-night stands. Let me preface my remarks by making clear that what I’m about to tell you is not a moral indictment. Rather, it is a bit of wisdom earned from some very long nights spent with some very sad strangers.

That said, here’s my first piece of advice: Avoid one-night stands. They are no fun.

Another note: This advice applies to lesbians only. From what I understand, gay men have mastered the art of impersonal sex, and I salute them.

Before you march over to your computer to type out an angry rebuttal, I want you to take an honest assessment of your sexual past.

Ask yourself these questions:

• After a one-night stand, have you ever skipped down the street (still wearing the clothes you were wearing the night before), happily telling yourself, “Oooh, I just can’t wait to have sex with a stranger again!”

• Was the sex you engaged in anything other than awkward, confusing, and kind of icky? Did it leave you with the same emptiness you feel after eating fast food?

• Did one of the two women involved break out in tears at some point, bemoaning the recent loss of a cheating girlfriend?

• Did your initial feelings for this stranger (lustful) deepen into something more meaningful (affectionate) or sour (regret or disgust) following the encounter?

Considering that every lesbian I know is either in a relationship or longing to be in one, I suspect 99.9 percent of all lesbians have had a pretty miserable history with one-night stands.

Here’s the biggest problem with one-night stands: Women rarely enter a sexual encounter thinking it will be a one-time thing. We don’t determine that it has a limited shelf life until we’re well into the fumbling sex.

So, disappointment is inherent in the one-night-stand. We either (a) Want the stranger to fall in love with us; or (b) Want to fall in love with the stranger, and when that doesn’t happen it’s upsetting.

But, we never learn from our mistakes, and we’re going to keep having one-night stands.

So, here are a few rules that will enable you to handle them with grace, dignity, and a bit of fun.

(1) Insist on spending the night at her place, so you can make a quick escape the next morning.

(2) Do not cry at any point during the encounter.

(3) Keep the sex simple. Don’t try any fancy stuff. You don’t know what she likes, she doesn’t know what you like, and you’ve got only one night to figure it out. So, stick to the basics.

(4) I don’t care how drunk you are, do not invite her to have breakfast the next morning with your parents.

(5) Do not fall into a relationship with her pets.

(6) Do not feel bad about yourself the next day. Giggle at your naughtiness. And don’t forget to take a hot, cleansing bath.

(7) The next day, call all your friends who are in relationships, and tell them about your encounter. They’ll act outraged, but actually will be pea green with envy.

(8) Give her a call in a few days, and tell her that you had a nice time, but make no plans to meet. This simple courtesy will make you each reevaluate the disappointing evening, and allow you to greet each other with real affection when you bump into each other again. Then, you can share a giggle over your naughtiness, but don’t sleep with her again. Remember: “One-night” has a well-defined expiration date.


Hey! I wrote a book. You can buy Dateland on www.amazon.com.

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