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Ask The Good Enough Guy: Too Soon For Sex?


Hi Will,

Here’s my question…

How soon is too soon to sleep with a man? I mean, in college we held off because we didn’t want to get a bad reputation. But let’s face it, everybody needs to get their groove on every so often and women are no different. So honest answer Will, would you ask a woman who slept with you on the first date, out for a second?


Melissa, New Orleans


What a dilemma! Not for you; for me! If I tell you that I think women should hop into bed with guys on the first date, I’m not really being honest with you (or with myself), but if my guy friends find out that I said that women should wait, I could lose my man-license.

Seriously though, asking how soon is too soon is like asking how long a piece of string is. Every woman is different. Every man is different. Then you have variances in thinking between the different age groups, nationalities, races (who DO think differently on things), and, of course, the religious ideals, which range from the church-warrior zealot, down to the atheist’s “hey, whatever…” attitude. There are just too many variables, and I always sucked at math. So…

I talked to a LOT of guys on this, which made the math worse instead of better. The barber shop consensus (which actually did take place in my barber shop) was pretty one-sided. The eight barbers and various customers, nearly all under the age of 30 and all still very single, believed that sleeping with a woman, even on the very first date, was not a mark for or against the woman. My own barber remarked, “If you hit it off immediately, and it’s obvious that there’s a strong chemistry between the two of you, there’s nothing wrong with it. It’s not like we’re back in the 80’s.” (Yes, he actually said “back in the 80’s,” like I learned to drive in a covered wagon or something. Don’t you just hate young people?)

However, friends in my own age group (39…ish) seem to see things quite differently. Their opinion, and mine, is more of a “if you’ll sleep with me tonight, what did you do last night?” type of mindset. As men, even as gentlemen, we will do everything within our power to be as successful as you let us, but that does not necessarily mean that we want you to let us succeed. My best friend (41…ish) said this about his wife; “We talked on the phone for weeks before we met, so we already knew a lot about each other, and the night we met, she was so fine that I wanted to (*too hot for GEM!*) At the end of the date, she told me that she wanted that too, but she wanted to know me better first and if I really wanted her, I’d have to wait for her. Even as much as I wanted her, if she’d given in, I don’t think I would have seen her in the same way the next day.”

My feelings exactly (sorry, guy-friends.)

BUT!!! There are some new twists these days. With the advent of social media sites and internet dating comes some new questions. If you’ve chatted, messaged, texted and skyped for months on end, sent pics back and forth (not the status pics of you from college, the REAL pics of you), if you’ve talked on the phone for hours every night, and have even changed your FB status to “in a relationship with”… is the day you finally meet still considered only your first date? I say, YES IT IS. Although we may feel like we really know a person on line, it’s far too easy to hide the things about ourselves that we don’t want others to know. I may remind you of Denzel Washington on line, but I’ll probably look more like George Washington in the morning… and who really wants to wake up next to George Washington?

You ask how soon is too soon, and a lot of that depends on what you’ll want to happen the next day. If a man sleeps with a woman very early on, he’ll more than likely call her again… every time he wants to sleep with her again. And he’ll probably assume that he’s not the only one calling her for the same purpose. For me personally, it speaks volumes when a woman wouldn’t think of letting a man borrow her car, see where she lives, meet her family (or children), or even see into her purse… but is willing to give her body to him.

Now, if said woman is simply trying to “get her groove on” and have her needs met, then as long as she is taking precautions and doing so safely, than I’d have to say, good luck with that. But, without getting too graphic, isn’t that just another form of masturbation? I mean, it may feel good, but is it really leading anywhere? Wouldn’t it be easier and safer to by an electric “friend”… and then buy a Kindle to go with it? That way, the next morning, at least you wake up with “someone” who has something interesting to say.

Is there a big double standard when it comes to men and women and their sexual misadventures? Yeah, that’s not a news flash. Will society look down on a woman for some of the same things that it pats a man on the back for? Definitely. As my kids are tired of hearing me say, “It’s not fair… it just IS.” It’s the way of the world.

But you didn’t ask the world; you asked me, so here we go in black and white. First off, would I call a woman for a second date that had slept with me on the first? Easy answer: For more sex, yes, for anything else, NO. Next question.

How soon is too soon? I’d say, at the very least, there should be seven dates, none of which can take place on the same day, at least one of which should include a close friend of his and one of which must take place at his home (and the one at his home should probably be a double-date or group-date-party-thing, for safety reasons.) Why seven dates? Because both men and fish get caught by their mouth, and if after seven dates, he hasn’t said anything really stupid, he’s probably a keeper.  Why meet his friend? Because if after seven dates, you haven’t met any of his friends, than he’s hiding something from you or he’s hiding you from something. Why one date at his home? Because if you’ve never been to his house, than either he’s married, he’s a pig, he still lives with mommy, or he’s homeless… and which one of those guys do you want to sleep with?

So there you have it, Melissa; Guy Sex Etiquette 101. I hope I helped. Now, if you see me next week, and my hair looks ridiculous, it’s because my man-license has been revoked, and I’m banned from my barber shop.

William Jones is originally from the tiny town of Alton, Illinois, and now lives in the tinier town of Reisterstown, Maryland. He is a happy husband and a proud father of three, and writes as a hobby, in those few, spare moments he finds between husbanding and daddy-ing.



  1. juli

    February 27, 2011 at 12:03 pm

    Nice answers Will; but I think you oughta know that this is 2011 and the toys are now battery the toys don’t kiss, or play with your hair, or snuggle a bit. If I’m looking to get my groove on, I don’t need witty conversation I just need sex. 😉
    But if I truly like a guy then yes I make him (and me) wait just so I’m not judged as a whore.

  2. Jennifer

    February 27, 2011 at 12:13 pm

    Excellent response. Excellent advice. I’ve never heard it put quite so well and I totally agree with you Will. Be well!

  3. Mia

    February 27, 2011 at 12:31 pm

    I agree with Will it all depends on what you are looking for, but I also think people are MUCH more OPEN-MINDED about sex, even older people.

    Be careful and be mindful. Run the scenario’s through your head on what you are looking for. I do think Will hit it on the head, asking questions like would you let them drive your car, have you been to their house, etc.

  4. LondonMUgirl

    February 27, 2011 at 2:23 pm

    I’m going to print this out and hand a copy to all my single friends. I totally agree about not being intimate with someone you wouldn’t let into your house.

  5. M.E. Johnson

    February 27, 2011 at 3:33 pm

    Great, Will, as usual. I’m glad you didn’t say do it when you’ll co-sign something (Never!). I watch too many judge shows.

  6. Kebran Alexander

    February 28, 2011 at 11:34 am

    I would add to Will’s comments that women set the table for their own happiness. While we all like intimate moments, women want stability and an emotional bond to follow. Men are generally content with the act, until he sees her differently. If a woman wants a man to be serious with her, she cannot allow him to enjoy her intimacy casually in the beginning. Once the bar of expectation is set with a man, you cannot ask him to endure more for the exact same benefits (If it was free before, why do I have to pay for it now?). She must require that he meets her standards of him over time before she does anything emotionally or physically intimate. If she requires nothing of him to receive benefits, she receives what she required. Anyone can be a star for a night. Can you keep my interest over time? I like a 90-day rule. It reduces the immediate impact of alcohol on judgment. He has to be present, active, and consistently meeting standards for 90 days before benefits. If she is content with him showing up before sex, she has a very low bar. If she wants conversation, sharing, and goals, she has time to discover the “real him”, if she asks the right questions and requires his answers to her questions. You have the right to place someone in situations that you like (movies, plays, opera, concerts, receptions, art shows, etc.) to see how this person complements your interests and to allow yourself the opportunity to see if you complement their interests. Worst case scenario, you find out that there is no sustaining interest. You may discover that they are more interesting than you thought that they might be. Either way, your decision over 90 days is with decidedly more information than one night, with or without drinks, provides.

  7. Shay

    March 1, 2011 at 2:05 pm

    As a single woman in my mid-30’s, I call bunk. A good man is a good man, regardless of when you sleep with him. If he’s going to be present, and interested, he will be. Period. Worrying about the “when” and “if” of sex puts pressure on your both that is really only wasted energy. If you’re dealing with an equally mature partner, then it’ll happen when it does, there is no rule you can state as being the “right” way.
    Should you set out to have sex the first night? Absolutely not. If you have that undeniable spark that just cannot be ignored, should you deny it just to prove some point? Absolutely not.

    One of the reasons women my age and older enjoy dating men in the 25-30 age range is their lack of caring about what society says that says about us. They typically don’t judge us based on when we sleep with them, or don’t, and they seem overall less concerned about whether we’re “good girls” or not.

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