Dear Em & Lo – How Can I Connect with Someone Before Sex?

photo from Summit Entertainment
Hello Ladies!

I am a single thirty-year-old woman who hasn’t had sex in a year. The problem isn’t that I couldn’t be having sex, I’ve got prospects, the issue is my desire to avoid the same patterns my relationships have followed thus far. I am genuinely sexually adventurous but I have realized in retrospect that I have used sex as a means of power and control and in doing so neglected my own sexual needs in order to please my partner.

I have used this time to improve my self esteem and deal with my abandoment issues and have made many realizations. I have realized that I have made myself a sexual receptacle, more like a toilet than a human, and that it is easier for me to be a “dirty” fantasy fulfiller rather than be vulnerable and connect emotionally. These facts terrify me. Still, I am freakin’ horny! I want to move forward! I want to have sex! I just don’t know how to go about it the right way.

All my relationships have developed sexually before intellectually or emotionally. I don’t know how to do it the other way. I have scoured the internet, the library, and bookstores for some book to help me but it seems like everything I find is either a book of sex tips written for women who have never masturbated and need encouragement to explore their own bodies. I am not afraid of sex, I just want to be able to have a healthy sexual relationship, one with equality. So ladies, any advice or recommended reading?

— Lady in Waiting

Dear L.i.W.,

Wow, you definitely win our golden dildo award for Most Self-Aware Emotionally Mature Advice-Seeker of the Month! Are you sure you don’t have your own personal advice giver on staff full-time? Because what you have accomplished already is beyond impressive — many women make it to 70 without figuring so much about their sexual selves. We’d like to say “you go girl” but we’re afraid that would date us so we’ll have to make do with an all-caps YAY! instead. And if it makes you feel better, we’re pretty sure that the hard part is over already.

Well, sort of. The hard work on yourself is over already; now you’ve just got to convince a good man to see the world — or, at least, the bedroom — the way that you see it. But here’s the good news: Any guy who doesn’t go for your approach to sex would be the wrong guy for you anyway. So even though it may take a bit longer to find a sex partner now that you’ve completed your self-esteem year, at least you know that when you do eventually end up doing it, the chances that the guy is right for you are way higher.

First of all, we recommend not seeking Mr. Right in a bar. Sure, some beautiful marriages have blossomed out of boozy bar hook-ups, but many many many more unsatisfying one-night stands have resulted. May we introduce you, instead, to the date? Tell any good friends whose taste you trust that you are ready to date again, and let them know that you’re looking for a good guy, not a playa. We’re pretty sure that any woman worth her ovaries will know exactly what you’re talking about. With any luck, you’ll get a few blind dates out of this. Of course, they may all be terrible, but this is a numbers game, and you have to kiss (or, rather, not kiss) a bunch of frogs first, as the story goes.

If your friends are all terrible matchmakers, then go online instead. While we don’t recommend actually including the line “no playas, please” in your profile, there are other ways to convey this — as your English teacher told you, show, don’t tell. Describe the kind of guy you’re looking for, describe the kind of relationship and connection you’re looking for. And when you’re checking out guys’ ads, be sure to ignore any profile with the “interested in play” field checked. Duh.

Once you’re on a date, it’s pretty simple: Don’t have sex on the first date! Repeat: Do. Not. Have. Sex. On. The. First. Date. Or the second or third, for that matter. We hate to go all Rules-Girly on you, but if you want a relationship to develop intellectually and emotionally first, then you’ll have to actually spend time together, intellectually and emotionally, first. We don’t mean no body contact — feel free to make out or dry-hump or do whatever you’re comfortable with. But hold off on the actual naked time until you feel an intellectual or emotional connection starting to form. If a guy tries to pressure you, just explain, calmly and matter-of-factly, that you don’t feel comfortable having sex until you’ve got to know him a bit better. This process may take a few weeks or a few months or even longer — it’s completely up to you. If he’s really into you, he’ll stick around (okay, maybe not for nine months, but he’s not going to dump you after a few dates — and if he does, you’ll know he was only in it for the booty anyway).

On a practical note — if you think you’ll be tempted to sleep with a guy sooner, take the necessary precautions. Perhaps it’s setting yourself a two-drink limit on dates, or asking your best friend to text you at 8pm, 10pm, and midnight remind you to keep your chastity belt on. Also, staying out in public (i.e. dinner and a movie theater rather than Netflix and take-out) will help both of you — it’ll help lower his expectations of booty, and will limit your temptation. Of course, you could always blurt out on the second date (not the first!) that you’re not going to put out easily so he shouldn’t go invading your dance space anytime soon. And if you can pull that off with eclat, then come back and tell us because we’ve got another medal for you.

You go girl,

Em & Lo


  1. I totally relate to Lady in Waiting. I got burned terribly in my early 20’s (I am now 35), and I emotionally shut down myself. I went through quite a few men without expecting to have an emotional connection. I came to realize not too long ago that it was my way of controlling and avoiding emotional vulnerability.

    Recently, I met someone new. Immediately, he picked on my emotional guardedness and suggested that we nurture a relationship by first building a solid foundation of friendship as oppose to agreeing to get romantically involved right away. I was taken by surprise but impressed with his intuitiveness: I am grateful for how much he cares about my whole emotional and physical being. At this time, I have no idea where our friendship is going. I am trying to focus on letting down my guard and letting another individual into my life and heart. It has been a painful process, to say the least, but I really want to be happy and enjoy the companionship and togetherness.

    It is not that I have any advice to share with Lady in Waiting or other ladies out there. It is just that I feel relieved to know I am not alone…

  2. misspiggy, and man can be a “Bad Boy” and still a fundamentally “good guy.” (And still be NASTY as hell in the bedroom!) They are not always mutually exclusive. 🙂

    Thank Heaven.

  3. In relation to Johnny’s spot-on advice, it might also be worth adding that, if you do decide you like ‘dirty’ sex, but on equal terms, it’s perfectly likely that a ‘good guy’ will be into that too.

    But you won’t know until you really get to know him, because he won’t reveal it unless he trusts you, and unless it’s clear that you want it. (On the other hand, with practice it does get easier to read the subtle signs that are there.)

    The main thing is to decide what you want – is it ‘good guy + nice sex’, or ‘good guy + varied and sometimes dirty sex’, or ‘good guy + always dirty sex’? Then you can get much better at finding what you want as you date. Good luck!

  4. I think there might be a missing part of the equation here. Low self esteem and abandonment issues can explain dating player jerks, I believe(I’m assuming they were jerks). There’s not much risk of getting too attached to a guy like that, so there’s no real abandonment when he leaves. And low self esteem makes one vulnerable to being treated shabbily and submitting to someone. But the “dirty” sexuality I see as something else. I agree with you that you use this as a means of control, but only in the sense of having control over something that was previously uncontrollable. What I’m guessing is that you may have been sexually abused in the past. Abuse is a very scary situation where one doesn’t have control. It’s been my observation that a person grappling with past sex abuse may act to firmly establish sexuality in their social interactions, even if it’s in a way that others perceive negatively. It’s as if the mind is thinking, “Well, at least I made it happen and it wasn’t some scary unknown quantity”. If I’m off the mark, I apologize. And if it’s depressing to think that you now have more to figure out after having figured out so much already, I’m sorry as well. It’s true that your actions make situations physical rather than emotional, but I believe that such profound physicality is there for a reason. Oh, and while you may have some control, in my mind, power comes when you’re able to have things come out how you want them.

    I truly wish you well.

  5. After reading the last few comments by Johnny, in different sections, I keep thinking how well written they are; giving us a guy’s perspective with honesty and humor. So, I’m thinking…Johnny should be one of the “Wise Guys”!

  6. Dear LIW,

    You’re going to have to get used to a new type of guy. That’s going to be your biggest challenge.

    Based on your description of your sexual history, you’ve been dealing with players. Also, though you may look back on your experience as a promiscuous woman (I’m not going to call you a ‘toilet’) with some regret, clearly you are a sexual, naughty woman yourself. That means you’ve historically been attracted to the guys who bring that feeling out in you – the aforementioned players.

    The type of guy to take you on 4 dates with no sex is not going to be that type of guy. he’s going to be a “nice guy.” Nice guys aren’t seducers. Even if he’s cool, you’ll likely see him as naive, over-sensitive and bumbling compared to the guys you’re used to. You’ll have to deal with them being “respectful” when what you really want is nasty sex. You’ll be shocked by how clingy these guys can be. You’ll smell their inhibitions, their reluctance or inability to rapidly stir a woman’s sexuality.

    These guys are great rapport-builders. They can make friends. They can have intellectual and emotional conversations. They’re likeable. But they stall out when it comes to sexual escalation. This is going to be foreign territory for you. You’re going to have to take them by the hand and walk them there.

    Good luck.

  7. Em&Lo to the rescue! Fantastic advice, ladies!

    I would also like to add, in addition to “real dates” not meeting in bars, or hanging around in either of your homes, where there is…..a bed, couch or floor only a few feet away, and the temptation (and often boredom of a shitty Netflix movie) can remove your self control, have DAY dates. You know, go to the Zoo, the Natural History Museum, the Library (really, it can be fun) the Aquarium, see a movie in the daytime, take a walk in the local forest preserve, go to a local Historical House. I found this really cuts down on the expectation of immediate sex after the date stuff is nearing the end.

    Try to make a pact with yourself. No sex for, say, 4 dates or 5 dates. Then, decide WHAT you consider a date. (His dropping off the sweater you left in his car, while you are on your way out the door to the grocery store doesn’t count! Neither does accidentally bumping into him at Starbucks or the library.)

    Waiting 4 or 5 actual dates may allow you to get to know him. While attempting to wait too long may drive both of you insane. You need to find a happy medium, which you will only know when you try it. (Hint, you’ll know his last name, his siblings names, where he grew up, and where he went to school.)

    Try to envision sex as the two of you *sharing* something fantastic, and remembering there is NOTHING wrong with putting the focus on YOUR pleasure too. Good men want to please you in bed and out of it. Take away the idea of sex as “giving” and try to view it as “sharing.” You seem very self aware and I think you can do this easily.

    Good luck, sweetie!

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