Thoughts From Guys On Our IM: When Do You Tell A Dude Sex Is Off The Table?

Ladies, get ready, I’m about to have a TMI moment with y’all. A couple of months ago, I went on a date with a guy, and we seemed to really be hitting it off. He made a comment about coming back to my house when we finished up our drinks, and I was really into the idea, but I didn’t want him to get the wrong vibe about what might go down, so I flirtatiously told him that I was up for it, but I wasn’t going to sleep with him. And. He. Flipped. Out.

He turned to me and said, “Just think about how this sounds” and then repeated my words back to me. “I’m not going to have sex with you tonight.” And oh, boy, was he right. It sounded HARSH. Way harsh, Tai. (“Clueless” reference alert!) I was suddenly on the verge of tears. I felt like a major jerk! And so presumptuous! Had I totally blown it? But then, what was I supposed to do? I mean, I was just trying to avoid some really awkward making out moment. My intentions were good!

So, I figured I’d ask a few of the thoughtful gents on my IM list what they prefer women do in those sorts of scenarios. And boy, were the results mixed. The general consensus though, was I probably shouldn’t have handled it quite that way. Lesson learned. It’s a good thing I’ve only been doing things this way for oh, the last 15 years or so. (Blergh).

After the jump, guy advice on how to handle the awkward first (or second date) sex chat.The Scenario: When you’re on a first or second or third date with a girl, do you prefer she say up front she isn’t going to sleep with you, or would you rather she set boundaries in the heat of the moment?


The Writer: I think I’m fine with either, but of the two, I guess up front. I mean, here’s the thing — a dude who’s cool should also be cool with it if you pull up short even in the clothes-off moment. If he’s playing the long game.

Me: They never are though.

The Writer: And if he’s not playing the long game, then you don’t need to sleep with him anyway. So as long as you were kind of flirty and fun about it and made it clear that you’re into him, I think what you said is fine and actually probably, as you said, kind of considerate. It might spare him a little embarrassment.


The Lawyer: If she wants to tell me upfront that’s never something I’ve asked for or expected, but I think I wouldn’t mind.

Me: Do you appreciate it?

The Lawyer: I might appreciate it IF, this is the obvious if, it were stated in a natural, non-offensive, appropriate way. If it were anything but, I think I’d probably immediately say, “What makes you think I wanted to f**k you, uggo?”

Me: Right.

The Lawyer: I really wouldn’t mind it if it were said appropriately. Like, if it fit the conversation. Something closer to, “It usually takes a while for me to get to the point where I’m ready to sleep with someone” versus “I don’t want to mislead you, so just so you know, we’re not having sex tonight.” That’s totally different and not okay. That’s the point where I tell her that I wouldn’t f**k her with Anthony Weiner’s dick.

Me: Why is it different?

The Lawyer: It’s making a huge assumption. Who said it was even on the table? That’s no different than me walking up to a random girl in a bar and saying, “Hey sorry, but FYI, we’re not getting married.”

Me: Ah.

The Lawyer: I just would object to the girl suggesting she’s taking something away that she thinks I wanted. If she presented it the other way, as a purely general comment, then that’s totally fine. And it would still communicate the message, and I think I would appreciate it.


Me: Would you prefer she tell you up front that she’s not going to have sex with you that night, or would you rather she wait until the heat of the moment?

The Editor: This question is problematic, as I would prefer neither. But if I had to choose, I’d choose the latter.

Me: Qhat would you prefer?

The Editor: I would prefer a magical reality where two people dating isn’t some kind of negotiation for sex. But that’s life! The problem with the first preference is it’s presumptuous. Well, maybe I didn’t want to have sex with you (a lie, but frequently are the lies we tell ourselves). The second preference suggests a person who is dishonest with themselves and their wants. Why are you dating if you can’t surrender to palpable chemistry? And if there is no chemistry, why are we on your couch, dry humping our brains out?

The Editor: Sex should happen, like a flash mob, only not so precious and liberal arts degree-y. Suddenly, you’re staring at the other, and then come the giggles, and then hot lava, only not hot lava, because that would burn the skin off your bones, but hot lava that is hot and fearsome but is actually more like a milkshake.


The Photographer: I think me personally, I’d rather know upfront. The reason being that if you’re in the heat of the moment and suddenly she pulls the e-brake you feel slapped across the face by rejection … not too pleasant. But if she tells you in the beginning it’s more or less rejection patting you on the shoulder saying “It’ll be okay … we can get through this” and you can still have a good time on the date … it’ll be awkward still but much more tolerable.


The Musician: I would rather wait until the heat of the moment for the following reasons: 1) I don’t like to schedule sex. It makes my dick soft, literally. Saying that, “I’m not going to sleep with you tonight” implies that it was pre-meditated an scheduled. 2) Women are known to change their minds. Maybe her opinion of you changes from the beginning of the night to the end of the night. I don’t mean that in a date rapey way. I mean. if it’s a first date or whatever, it is your job to shatter her ideas of who she thinks you are. So yeah … also if the relationship ends up going anywhere, the idea of sex being this thing that she can dangle in front of you will be a point of contention in the long run. I just prefer it to happen organically even if that means not getting any.

Me: Okay, so what do you do in the heat of the moment though, if there are moves made and then you’re rebuffed — isn’t that majorly awkward? To get less vague—you try sticking your dick in her vagina and she’s like, “NO.”

The Musician: I’m more of a slow moving kind of person in the heat of the moment … it takes me a while to even get there.

Me: You’re the slow loris of sex.

The Musician: So that way there is plenty of time for her to be like, “Let’s not sleep together, let’s just 69 or whatever.”

Me: Well, this has been very helpful, and now I’m going to picture you as an adorable slow loris. Win-win.

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