Wise Guys – Would You Accept a Free Pass for a One-Night Stand?

photo by balinto

Advice from three of our guy friends. This week they answer the following: “If a guy’s partner told him that he could have a one-night stand with a stranger, no questions asked, and it was guaranteed that his partner wouldn’t freak out about it later — would most guys take their partner up on the offer?” To ask the guys your own question, click here.

daniel_100Gay Single Guy (Daniel): Let me put it this way: if a guy’s partner gives him the okay for a one-night stand, he will keep it in his back pocket even if he never intends on cashing in on it. It isn’t really about going and doing it. It’s about having the option, and all men would reserve that option if you grant it to them.

mark_luczak_100Straight Single Guy (Mark Luczak): Wow, thanks to Em & Lo for waiting until I was actually in a relationship to hit me with this one — watch me tread like 7,000 times more delicately now. This falls under that always-entertaining “what if” umbrella — thought-provoking, revealing, even titillating, and always great conversation fodder.

My initial reaction was to latch onto the “stranger” aspect — does the fact that the guy wouldn’t know anything about the person beforehand actually lessen the appeal of the whole affair, or does it actually help with the disconnect of this one-time occurrence never to be spoken of again? It’s safe to say the whole idea would be incredibly tempting, especially since it includes the implicit approval of the partner (thereby distinguishing it from the same scenario but with the exception that the partner would never find out — a sequel for a future Wise Guys installment?). But if the relationship is strong enough, like mine — Hi Honey! — there’s no inclination to stray, even once, under any circumstances.

james_glazebrook_100Straight Married Guy (James Glazebrook): The only way I can picture this happening is in a similar scenario to the Curb Your Enthusiasm series when Cheryl permits Larry one last fling, safe in the knowledge that he won’t be able to pull it off. My wife knows better than anyone how little “game” I have – it took me long enough to pluck up the courage to even kiss her. Besides, even if I could “seal the deal” I’m a notoriously bad one-night stand, only capable of performing in that sweet spot between being drunk enough to feel nothing and so wasted that I spew and pass out. So, all ethical considerations aside, I wouldn’t bother, no.

Our “guys” are a rotating group of contributors. This week’s Straight Married Guy is James Glazebrook of Most Likely To; our Gay Guy is one-time stripper and sex columnist Daniel; and our Straight Single Guy is Mark Luczak, a tech geek at Carnegie Mellon University. To ask the guys your own question, click here.


  1. I don’t agree its a trap. While I would not want my husband running around with half the female US population, but I would like to see him have sex with another woman. Never told him this, but I’d find it a big turn on!! My only fear is that he would continue to use his ‘free pass’ repeatedly and I’d not be a fan of this. Who knows, maybe I’d join him and we’d make it a three-some!

  2. No woman is going to give her man a free pass. She will make sure he pays dearly for it the rest of his life.

  3. This wouldn’t work for us. I offered to do a two women on him threesome. He flat out told me NO WAY! If he isn’t willing to share, there is no way he would even consider a free pass.

  4. ^ Yeah, well… to quote Tony Soprano, “don’t put me to the test.” I don’t do tests. If a woman wants to test our connection, the right way is to ask me NOT to sleep with other women.

  5. Danger, Will Robinson!

    Anytime a woman makes an offer like this, it is a trap. for some reason, she’s feeling dwn and needs some kind of a boost from her partner, yet doesn’t cut him any slack in seeking it. The offer itself is a test of her man’s connection to her, and any interest shown in actually accepting this offer is seen as a betrayal and leads to a huge fight which destroys what intimacy might once have been possible. Be forewarned, guys!

  6. Like Mark I latched onto the “with a stranger” clause. Back in the 1980s one of the big researchers (Shere Hite, I think but please don’t quote me) noted that while fantasies are all over the map, women are more likely to fantasize about sex with strangers while men are more likely to fantasize about someone they know.

    To the extent those stereotypes would be true (however true a stereotype can be for any one individual) then I’d look at the offer as a very generous gesture based on the partner’s own Erica Jong-style ideals.

    For me, at least, the “one night with a stranger” scenario probably wouldn’t be as safe as the word “stranger” implies. Because while I’ve been pretty promiscuous I’ve never managed to have sex with someone without getting to know them. Even if you don’t get to know them beforehand it’s kind of hard not to get to know them during and after. Not to mention a little weird.

    So if it were me, rather than preferring Erica Jong style “zipless” no-strings sex with a stranger, I’d much rather have no-regrets sex with someone I knew and trusted enough that we could agree to, and stick to, a one-time thing.

    Cool question.


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