About four months ago, I reconnected with a college boyfriend on the Internet, and we began talking over the phone. Although we currently live 400 miles apart, I will be moving back home, near where he lives, in about six months to be with my family.

He has just recently gone through a hurtful divorce and is now battling to see his daughter. In the beginning, he and I just kept it pretty casual, venting, chatting and catching up. After a while, there were a couple of times he tried to seduce me over the phone. I asked him to not go there, because I was not comfortable going there just yet. He was persistent, and one night, he caught me at the right moment. I normally won’t allow myself to invest in a sexual relationship (if that is even what you call it) unless I am very clear of the boundaries. Also, I have never had a sexual phone relationship before.

I have noticed since this has happened that he is different with me. He still calls; however, now he tries to discuss sex often. And he complains that he has to sleep alone and doesn’t get to have sex because I live so far away and haven’t come to visit him. He’ll also go for periods of time without calling.

In a month, I am planning to go home for a week. I’ll have a chance to visit with him then. I find that I am pulling myself back emotionally many times because I am not sure what is happening. At times I want to just go the other way….far away and fast. However, I really feel like I could (and even think that sometimes I already do) care deeply for him. Yet, I do not want those emotions to cloud my reasoning or judgment. So here I am seeking your advice… can you please help me make sense of all of this?

Laurie

Apparently, it’s Sex Month on Advice from a Single Dating Expert.  And Laurie, I’m afraid I don’t have good news for you.

You’re the phone sex girl.

It’s sort of like being the out-of-town girl, except, well, you never actually see each other, you just make noises on the phone.

If you don’t recall or are too lazy to click on the above link, this is the definition of the out-of-town girl: If you’re an out of town girl, you have a guy who lives at least two hours away who has been sweet talking you for weeks or months. Finally, you let him visit you and you have an amazing, memorable, erotic weekend together. The second he goes home, he does the slow fade. No more inquiries about your day. No more cute text messages to say he’s thinking of you. He got what he wanted, and maybe, just maybe he’ll call you again the next time he’s in town. More likely, he’ll call you when the girl in his area dumps him and he needs a quick pick-me-up.

It’s that once you’ve broken the seal and established yourself as phone sex girl, it’s hard to be anything else.

If you’re reading this and it’s sounding familiar, look in the mirror. You’re being used right now. Which is fine, if you’re using him as well. However, if you’re anything like our sweet, original poster, Laurie, you probably have feelings for this cad, which are not being reciprocated. It’s time to cut bait.

Does this mean a woman should NEVER have phone sex with a guy, or NEVER sleep with a man after months of long-distance courtship? Not at all. If phone sex and long-distance never amounted to anything, the only businesses left standing would be AdultFriendfinder and some Russian mail order operation. Listen, I’ve driven to San Francisco to meet an online phone sex partner, and I’ve flown to New York to go on a four day date with an intense phone connection. They COULD have worked, but only when there’s intent on both sides to make it work.

As a woman, all you have to do is observe a man’s behavior and determine whether it’s the behavior of a man who desires a relationship with you. Exhibit A: he’s recently and bitterly divorced, he goes long periods of time without calling you, and when he does call, he goes straight for dirty talk. Does that sound like Mr. Right to you?

I think your solution is obvious, and the lesson goes out to anyone else reading this.

The problem with being the phone sex girl is not the phone sex. It’s that once you’ve broken the seal and established yourself as phone sex girl, it’s hard to be anything else.

Put it this way: while you’re emailing me about how you’re rekindling long-dormant feelings for an old flame, he’s probably bragging to his guy friends that his ex is getting him off on command.

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Hi Evan,

How do you avoid putting "notches on your headboard" while dating, yet still enjoy a satisfying physical, monogamous relationship? I am a 52 year old attractive woman, and I have been dating online for about 4 years. I haven't had a problem meeting lots of men with whom I have chemistry. While I don't jump in bed with them right away, we will have sex once we get to know each other.

The problem is, most people will put their best feet forward in the beginning, and so you start having the physical relationship, then at about the 6 month mark, the red flags start glowing. You may find out his idea a good credit score is being one step ahead of foreclosure or you may meet his family and you realize you aren't going to be happy listening to the banjo on the front porch.

While I think of myself as pretty discerning and have high expectations, I have taken your advice and widened my parameters. However, it seems in the last 4 years online dating is making me feel like an "Online Whore." What's a woman who enjoys a physical relationship and wants to be monogamous to do? Do I have to just think more like a man? It seems in this day and age, trying to wait for sex until you know someone thoroughly isn't realistic. I am right now taking a vow of celibacy.

Frustratingly yours,

What you call being an ‘online whore’ is what other people, including myself, call ‘dating’

Mary

Great letter, Mary. The banjo part nearly gave me the chills.

However, based on your text above, it doesn’t seem to me that there’s ANYTHING wrong. What you call being an ‘online whore’is what other people, including myself, call ‘dating’

That’s right, Mary. Unless you still buy into Mom’s explanation of sex – ‘When a man loves a woman’ intercourse tends to happen before marriage. It happens before the six month mark. It happens before the declaration of love. And hey, if you’re lucky, it can even happen before the entre. Point is, you’re conflating two different points and coming to the wacky conclusion that a vow of celibacy is just the right tonic.

Yeah, I can’t think of a better solution for a sensual woman than to swear off sex.

Your issue isn’t with sex. It’s with your antiquated, double-standard view of sex. That’s right. You’re still obsessed with the number of people you’ve slept with, when, you know what? Nobody else cares. ‘Notches on the bedpost’ Not even GUYS talk like that anymore. If you sleep with men you’re seeing for two months, four months, or six months, you’re not a slut. You’re a normal, sexually active woman. And you need to stop beating yourself up on yourself for racking up numbers. See, unless you get hit by a bus, your number just keeps going up and up and up. …

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My boyfriend and I have been together going on 4 years. We have moved in together and overall, it seems that we are making the steps to build a loving future together. Until, that is, the beginning of February.

While doing some maintenance work on his computer, I came across pictures of his sister’s friend, who was topless. He claimed he had asked her to stop sending them and had only saved the pictures as a way to insure she would. I accepted his explanation as I have never had reason to distrust him in the past.

Well, a couple months later, I found an inappropriate picture of a female coworker whom I thought had a crush on him. I talked to him about this, trying to be as emotionless and non confrontational as possible. I explained to him that I can’t stop some girl from sending him pictures, but HE has the power to delete them and put a stop to it.

Since that talk, I’ve found other pictures of his friends in various stages of undress: a high school friend laying in bed with her breasts exposed and another woman fully nude. We had a huge blow-out about it, and I told him I’m going to leave if it doesn’t stop. He begged me to stay, says he’s so sorry, that he didn’t mean to hurt me, doesn’t know why they send him pictures etc.

I’m pretty sure he’s not physically cheating on me. We spend almost all our time together, and besides these pictures, he behaves normally. Our sex life is good, we go out, we genuinely enjoy each others’ company. So what’s his deal? Does he just want to get pictures of girls he knows for fun? I mean, I don’t care about porn; that’s fantasy and healthy. But I do have a problem of pornographic photos of girls he knows! I just need some perspective as to why he’s doing this and is this a valid reason to end our relationship?

Nichole

You’ve come up with a real doozy! I mean your boyfriend, of course, not your story.

You ever hear the adage, “Fool me once, shame on – shame on you. Fool me… you can’t get fooled again. Wait, that was the George W. Bush version. What I meant to say, Nichole, is that your boyfriend is playing you for a fool, and, at a certain point, the responsibility falls upon you to take action. That point was about three nude women ago.

Now, when you’re dealing with a four-year relationship in which you’re living together, “taking action” is not something that should be undertaken lightly. Before you pack up your things and move out, you need to have an authentic conversation with him. My concern, naturally, is that he’ll say all the right things to keep you, thereby setting you up for your fifth rendition of “fool me once”.

It’s clear, Nichole, that you WANT to believe him, because breaking up would send your life into turmoil, because blinding yourself to the truth is easier than facing it. Otherwise, I can’t think of any other reasons that a bright, self-aware woman who calls porn “healthy” would believe a whopper like:

He claimed he had asked her to stop sending them and had only saved the pictures as a way to insure she would.

Um, I don’t get it. I mean, I’m turning it over logically in my head, and I just can’t follow. If he retains the pictures on his hard drive, it PREVENTS more pictures from coming in? Who knew? …

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I’m 25, and Jewish but totally secular and non-practicing. I’ve been dating a Catholic guy for about two months. I knew he was Catholic at the outset, but I didn’t know quite how Catholic. Well, he’s pretty damn Catholic. I’m fine with the whole Jesus thing, but this guy doesn’t believe in pre-marital sex! But I really like him and want to be in a relationship with him. But…I don’t want to be in a relationship with someone who doesn’t believe in pre-marital sex! So I have a dilemma. I keep thinking that I can convince him, rationally, that the Catholic ban on pre-marital sex is a stupid, pointless anachronism that is not relevant to today’s world. He’s intelligent and educated and responds to reason; I think I have a shot at changing his mind. I’ve told him very explicitly that I think his beliefs are wrong and I plan to try to change his mind. He seems fine with that.

I mean, in some sense I’m tempted to just try and seduce him. (We haven’t done more than make out, at this point.) But I wouldn’t feel right about that, and I wouldn’t want to sleep with him if he would feel guilty or regret it afterwards.

I guess my question is, do you think it’s possible to talk to him about of it? Is it disrespectful to someone’s religion to set about convincing them that they’re wrong? (I really don’t respect religion very much, but I try not to be polite about it.) And, finally, even if I were to convince him and we did have sex, would he be constantly plagued by lingering guilt and fear due to the years of brainwashing he’s experienced? Is there hope for my project, or should I try to find someone whose beliefs are more compatible with mine? He’s really really great aside from the whole religion thing, and I think there’s serious potential here.

Just as background, he had a serious girlfriend for two and a half years. They never had intercourse, but did have oral sex, and he’s said he was "never really comfortable with it". He’s dated a few other girls but never so much as kissed them. So I take the fact that he’s willing to kiss me as an indication that he must like me…

Julia

Implicit in believing your own bullshit is the idea that people who disagree with you are WRONG.

I’m running your letter, Julia, because it’s a nice tie-in to the emails from virgins who are wrestling with their anachronistic worldview. You and me, Julia – we’ll corrupt all of their minds one of these days!

I’m kidding, of course, because, as you know, it is not your job to change anybody’s mind. I give advice for a living and, frankly, I don’t see it as MY job to change anybody’s mind. The difference between us, Julia, is that people come and ask me for advice because something isn’t working in their life. They’re looking for clarity, perspective, a kick in the ass. The Catholic guy isn’t looking for ANY of that with you. He isn’t asking you for spiritual guidance – he’s asking you to enjoy spending time with him and consider a life partnership. Thus, imposing your evolved point of view against his “brainwashing” is somewhat of an exercise in arrogance.

Believe me, I know. I’ve been called arrogant more than once, mostly because I so strongly believe in my views and can ably articulate them. However, implicit in believing your own bullshit is the idea that people who disagree with you are WRONG. And even if you’re an secular atheist Jew like me, it is certainly not your place to tell anyone in the world that they need to come around to your way of thinking. In fact, it sounds like a colossal waste of time and energy…. 

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Somehow, I’m one of them…

And as wary as I am of people who give advice, I suspect that out of 21 different authors, you’re bound to pick up a few golden nuggets of wisdom.

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Your friend,

Evan