I'm over 35 and dating. One question I get asked a lot is about my past relationships.

The problem is, I haven't had any.

I've had one problem or head trip after another. I've also been a loner and a bit of nerd. I can honestly say that I am over all of that.

I know these women are asking me this question to screen me out, the way an employer would look at past work experience.

I know I am a sane, well-balanced guy who will be considerate, but I am afraid that if I am truthful before I get to know a woman I will get dumped by the second date.

Any advice on how to handle this question?

Robert

Dear Robert,

Among the most common advice given by relationship experts is this doozy:

“Just be yourself!”

Tell that to the guy who asks a first date if she likes anal sex. Or the woman who complains that all men are pigs before she’s even ordered her Caesar salad.

Encouraging these folks to be themselves is a crime against humanity. They’d be far more successful on dates if they were to try to be anybody else. Of course, these people never learn from their mistakes, since they never get any feedback. When others don’t return their calls, they assume that it’s the other person’s loss, and tell themselves others are crazy for not appreciating their “honesty” and “directness”.

“Hey, I’m just being MYSELF here. You don’t expect me to just LIE, do you?”

Uh, if not telling her that she looks fatter than her photo is a lie, then, yeah, lying’s not a bad idea.

Which is just a long way of saying, Robert, that full disclosure isn’t always the best idea. Listen, I’m not one to make dating sound like a series of job interviews, but if you think of each “interview” as a chance to make a strong first impression, you don’t go into an all-out confessional.

“Yeah, see that line on my resume that shows that I was employed at NorthStar Research in April ’97? That’s because my boss was a dick, who caught me surfing for porn during a sexual harassment training session. Plus, the job really sucked because he was always asking me to do stuff for him…. My greatest weakness? Probably that I’m lazy. And a stoner. A lazy stoner.”

This is not how to interview. We know this. But it doesn’t stop us from telling the whole truth on a date under the guise of “full disclosure”.

Dating has always been a perfect example of “don’t ask, don’t tell” and I’m always amazed when not everyone has read that same rulebook.

Dating has always been a perfect example of “don’t ask, don’t tell” and I’m always amazed when not everyone has read that same rulebook. Like when you go out with someone who says that she’s got another date tomorrow night. What good could POSSIBLY come out of me knowing that right now? Well, in her mind, she’s just telling the truth, letting me know that she’s got other options, perhaps informing me that she’s not that interested. But chances are, she’s not sending a message. She’s just being STUPID….

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I’m a 42 year old woman, newly single. I’m just re-entering the dating fray for the first time in many years, and I discovered very quickly that I have no idea how to identify men my age who are single and looking. They sure seem to be scarce, compared to when I was in my twenties! I’ve chatted up guys who turned out to be gay or attached – they were just extremely friendly/chatty, which I occasionally mistake for an interest in me. And I’m too shy to laugh off any misunderstanding with a comment like, “Well, if you have any single brothers or friends, here’s my card!”

I’m dating online, but I’d also like to meet people in other ways.  Yes, there are the singles events, the frozen food aisle during off-peak hours, etc. But for other situations I may find myself in – elevators, gyms, coffee shops – do you have any suggestions on how I could strike up a breezy, innocuous conversation and still be able to “out” single men?  The “Wow, nice jacket – did your partner pick that out for you?” line doesn’t seem too subtle.

Thanks very much for any insights.

Enjoy your blog, loved your book.

Linda

Love your attitude, Linda. It’s tough out there, all right, and the healthiest approach is to do exactly what you’re doing. A combination of online dating, singles events, and real-life interactions, all of which create the greatest number of opportunities to meet single men.

That said, it’s not your job to “out” single men.

Because single men have been socialized well enough to know that it’s their job to initiate conversation with you. And if they don’t, they’re going to go home alone AGAIN. I’m not suggesting that this is a biological imperative or that nothing good has ever come from women asking men out. Still, as a dating coach, I’m a big believer that your primary job is to create the opportunity, not to seal the deal.

Your primary job is to create the opportunity, not to seal the deal.

Check out this short clip from a presentation I made in which I discuss how women can create opportunities with men. It’s at the very end of the five minute montage and it starts with “So if you want to meet a guy at a party…”. To sum up, it’s not your position to ask him out. All you have to do is make eye contact and smile. This gives him  permission to come over without being afraid of being shot down. Because that’s every guy’s concern, especially nice guys. We HATE feeling like fools. We HATE rejection. And we’d just as soon not even approach you, since it’s easier to go home and say, “Man, I wish I said hi” than it is to put our fragile egos on the line. The only way to get an insecure guy to come over is to let him know it’s going to be okay if he does.

Rachel Greenwald discusses her proactive approach for women in her book, and my friend David Wygant’s book “Always Talk to Strangers” is also illuminating, although it’s more written for men. But it sounds like you really have two questions, Linda – you want to “out” single men and you want to find pithy pick up lines as well….

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Evan,

I’ve just started dating a man I’ve known for several months. We both work in an industry that doesn’t pay much. My salary is good but normal for this profession and then with the supplement of my alimony settlement, I’m doing very well. He, on the other hand, is an artist/professional who has a hard time doing the whole "normal" work thing. Suffice it to say that he is dirt poor. Just tonight, he asked in a meandering sort of way, why I would want to date such a poor guy like him when I could have a rich man. He knows I was married to a man who made good money and that my last relationship was with a rich man.

I like this guy. He makes me laugh a lot, almost constantly. He’s delightful. He’s kind and generous and giving. He is compassionate and intellectual and kooky. I haven’t had this much fun with someone in years. Our dates last seven and ten hours. We like each other a lot. And we’ve yet to sleep together. He’s even thoughtful when it comes to sex and doesn’t push me at all. Well, hardly at all. My point is that he’s just delightful — why wouldn’t I choose him over some schmo with a fat bank account but a slim personality? It seems obvious to me — why doesn’t it to him?

So my questions are: how do you convince a poor guy that you really do like him? Will it niggle at the relationship forever or can you both get over it?

Samantha

What a wonderful question and a wonderful sentiment for the new year. I only hope you can spread some of that pixie dust on everyone around you, since you clearly know what relationships are all about.

But here’s the deal on your guy. He’s insecure. Insecure that he’s not a good provider – and insecure that a quality woman like you might not be open to dating him. Of course, there’s one other sentiment that bears mentioning, as much as we’d rather not acknowledge it: money actually matters in the long run. That’s why it’s one of the most common causes of divorce.

He’s insecure. Insecure that he’s not a good provider- and insecure that a quality woman like you might not be open to dating him. 

That said, I’m not here to convince you that money matters. You’ve been on both sides of the tracks and you’ve made a great case as to why you prefer this man. So why doesn’t he get how amazing he is?

Well, why does anybody lack in self-esteem? Mostly because society (or parents or peers) have pounded the idea “I’m not good enough” into most of our thick skulls. So women who are overweight have to deal with overweight men who crave airbrushed supermodels. And men who are short can’t get anyone to give ‘em a fair shake. And men who have no money are made to feel inadequate.

I know it well. I never made more than $39,000 until I was in my 30’s. In 2002, I was answering phones at an online dating company while I put myself through film school….

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Hi Evan,

I’ve enjoyed both your books and your blog, and have two questions regarding the email process of online dating:

1) If a man writes in his first email that he wants to meet and/or talk on the phone, is there a way to suggest a few emails first? Moving to phone right off seems to be the kiss of death.

2) In emails with men, at times they forget to ask any questions, so responding to their emails is a challenge. Is it best to just let those go – or is there a polite way to say “If you would like to keep communicating, a few questions from your side would help”?

Thanks

Joanna

Dear Joanna,

Let’s take this opportunity to talk to men, shall we?

Dear Men,

You’re bright. You make a decent living. You’ve been around the block once or twice. You’ve certainly been socialized well enough through school and work to know how people act.

So why would you think that a smart approach to charming women online is:

“Hey, great smile. Loved your profile. Think we have a lot in common. Call me at 323-555-1212.”

Could you imagine doing this in any other arena? Going up to a strange woman at a party and giving her your phone number before you got her name? Asking her for personal information before you’ve exchanged pleasantries? This is the equivalent of sex without foreplay, fellas, and women HATE it.

And rightfully so.

Any woman who has an ounce of self-esteem should value herself enough to turn all of you tactless, impatient, schmucks down. And you KNOW this. Which is why it kills me even worse that you don’t learn.

Seriously. Picture some woman coming up to you and asking you how much you made for a living. Or perhaps quickly trying to gauge your penis size. Her defense? “I don’t want to waste my time.” Which is pretty much your defense for offering to go to the phone before she’s comfortable.

And if simple courtesy isn’t enough reason to heed my advice, how about this: your way is ineffective. In fact, 80% of the men who put their phone number in a first email do NOT get emails back. You know why?

In fact, 80% of the men who put their phone number in a first email do NOT get emails back. You know why?

Because women want to be courted, needed, valued, and charmed. And just because you’re artlessly writing to dozens of people doesn’t mean that any of them want to feel like a piece of meat. Yet how else can one of your prospects feel? You’re not getting to know her, you’re not showcasing your wit, you’re not laying the groundwork for a great first date. You’re simply trying to secure her phone number with the minimal amount of time and investment.

Newsflash: women WANT you to invest time in them. That’s what shows them you’re serious.

I can’t believe I have to explain this to you!

Class dismissed.

Evan

So, Joanna, how do you deal with men who are clueless and pushy?…

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My boyfriend and I are both in our mid-40s and divorced.  We have been dating for 5 months and were friends for 5 months before that. 

Two years ago, when he was married, one of his staff, who was 17 years younger than him and engaged, invited him to a hotel room and so began a 5 month affair.  She broke it off with him to marry her fiance.  My beau was devastated and left his marriage. 

I met him a year after the break up with the mistress and he was still very much in recovery mode over this young woman.  I don’t think it helped matters that she stayed in touch with him and would invite him to lunch and coffee on occasion. As I got to know him, he seemed to finally recover and then we started dating.  But right at the beginning of the dating phase, I told him I would not get involved with him if he was still in contact with his former mistress. It made me uncomfortable. And for 3 months, he wasn’t.

But the former mistress (who thankfully now lives an hour away) was in town and invited him to lunch about a month ago. My beau decided then that he wanted to maintain a "casual intermittent" friendship with her.  I had been upfront with him in the beginning that I wouldn’t be comfortable with this so an argument ensued.  He assures me that he is crazy about me and feels nothing towards her and I believe him.  He says it’s a no big deal friendship – to which I pointed out that her husband and baby would probably feel differently (he knows nothing about her affair).  

My guy really is a great boyfriend and has been so good to me.  So what to do?  Why am I still so uncomfortable about this "friendship"?    

Thanks!!!

Jeannie

Dear Jeannie,

I’m on your team with this one. And I’m struggling with it.

Because there’s this voice in my head that says, “Trust is the basis of any relationship. If you can’t trust, you should get out.” But I don’t think you should get out. And I don’t think you should tolerate him being friends with his former homewrecker either.

Now, I’m all about letting people be. Call me a social libertarian, but I’m pretty much always going to side with the person who is asking for more freedom. If he likes to flirt, he’s going to flirt. If he likes to do drugs, he’s going to do drugs. It’s not your job to change him. All you can do is determine if you’re willing to put up with his behavior. And if you’re not, you’re well within your rights to leave.

But this situation strikes me as something more specific and insidious. Because you’re not trying to stop him from seeing his drinking buddy. You’re not jealous of his cute, young assistant. You’re not trying to keep him away from his ex-wife, with whom he shares custody of his child. You’re merely trying to keep him away from the very woman who (with his consent) RUINED his previous relationship. Not only should you be uncomfortable, but the mistress’ unwitting husband should be as well.

You’re merely trying to keep him away from the very woman who (with his consent) RUINED his previous relationship. 

And as much as I’m always going to tell women, “Don’t tell men what to do. We don’t respond to it,” I think you need to lay down the law on this one. Because, while it’s nice to trust, it’s also silly to leave your keys in your car….

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I’ve been dating this girl for two and a half years now – not just dating, but living with, I think that makes it all the more serious.  We were good friends for a year before all this, which is why we were comfortable with starting dating and living together at the same time…  The problem, I think, is that while I was her first, I had prior sexual experience with former girlfriends.  Maybe it’s my fault, for wanting to broaden her mind, but now she’s assured me she’s going to have sex with another man, no one in particular, but just because she wants to have a certain level of experience before she commits. 

Last summer, we had a "break", some time apart, and I know she’s been with another guy, though just oral sex.  Even though this devastated me, I agreed to get back together – she says she’s glad to have had time to figure things out, and in a sense, so am I.  But now I’ve become more insecure about all this, and certainly this jealousy is putting a strain on our relationship.  My problem is, she’s sure she’s going to sleep with another man, and that she doesn’t want to commit until she’s had "adequate" experience with sex and men; on the other hand at the moment we really are in love, and really enjoy being together – we can both imagine a long-term future together. Am I just avoiding future heart-break by not finishing it with her right now?  Are we too young to marry (we’re both in early early twenties)?

I feel silly writing to an "internet dating expert" (don’t take this personally!) but I don’t know who else to turn to. 

Love is complicated.

Thanks,

Chris

Love is complicated, Chris, and I’m sad to report that it just gets more complicated. The more you know, the more baggage, the more responsibilities, the more you realize you don’t know.

The more you know, the more baggage, the more responsibilities, the more you realize you don’t know.  

So just be glad that you have many years to get burdened with the weight of life experience. In the meantime, to answer your questions in reverse order:

Yes, you’re silly for writing to an “internet dating expert”. As you know, everyone who dates online is a loser who couldn’t succeed with the opposite sex in real life. And when you account for the fact that I’m a 35-year-old single guy who has never had a relationship over a year – well, let’s just say you should be very embarrassed for even talking to me. I’m sure my clients, girlfriend, and mom all feel the same way.

Next: Yes, you are too young to marry. Sure, there are exceptions to every rule – my girlfriend just introduced me to her friend who got pregnant and married before she was 20 and they’re still together at 38. But this is beyond exceptional. Today’s generation – and even my generation – Gen X – can’t compare ourselves to our parents. The world has changed too much and everything seems to have been delayed ten years. I am of the full belief that 30 is the new 20, 40 the new 30, 50 the new 40, and so on. It takes longer to choose and establish a career; we have infinitely more dating choices; and gender roles and needs have morphed considerably. So while it would be nice and nostalgic to return to a time where 22 year olds had kids and grew up with them, like my parents did, it’s highly unusual. People simply change too much in their 20′s and 30′s….

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Hey Evan,

My boyfriend and I have been dating for almost two years now, and everything is great, I couldn’t have found a more caring, wonderful person. He even loves to spend time with my family. I know he is planning on proposing soon, and for the most part, I am really excited about this. I love him. But we have some really big issues when it comes to our sex life, or lack thereof.

A few months after we started dating, we had sex, or I guess that’s what you could call it. Anyway, I wasn't complaining, even at 27, I didn’t have a ton of experience – I had only been with two other men. But then he never wanted to work on this issue, never wanted to approach it. Instead we would make out and then he would just prematurely stop at a certain point. I felt like I was in high school again. Eventually, about a year into the relationship he came clean and admitted that he was a virgin, had lied to me and had sort of freaked out when we slept together. 

I was upset at first that he had been lying for an entire year, but I can understand how difficult it can be for a guy to admit that and then to admit that he was lying.  However, it’s been another year, and he hasn’t been able to get past this, and I have just about given up on ever having sex again. Actually, I put an end to any physical relationship between us almost 9 months ago just out of sheer frustration. 

I have tried talking to him about this so many times, I have tried everything short of counseling and I just don’t know what to do.  I have asked him if this is something he wants to wait till marriage for and he denies that…I guess I just don’t know what to do.  I love him, and I know he loves me…but how can I resign myself to this for the rest of my life, at the same time how can I break up with a guy that I so want to be with?

Desperate

Dear Desperate,

You’ve got a big problem, all right.

And if you’re gonna solve it, you have to put yourself outside your comfort zone.

See, the thing with comfort zones is that they’re, well, comfortable. But just because something is comfortable doesn’t mean it’s healthy or good or ideal. It just means it’s comfortable. And the longer you stay in that comfort zone, the harder it is to extricate yourself from it. Consider a job where you’re happy with your co-workers, but severely underpaid. Or a job where you’re paid well, but you hate your work. There’s a strange sort of comfort in grumbling about the same sticking point over and over – knowing full well that it will never change. Apparently, it beats the alternative of getting another job.

You can complain all you want about the state of your sexual relationship, but apparently it doesn’t matter all that much. Because next thing you know, you’ll be married. Married to a man who doesn’t want to sleep with you. And who’s fault will that be? Not his. He’s getting what he wants, a sexless relationship. You’re the only one who is silently suffering. You are what psychologists would call an enabler.

You are what psychologists would call an enabler.

Because it takes two to tango. A woman can’t be a battered wife unless she stays in a relationship with a man who beats her. A husband can’t continue to be emotionally abused by the wife he left behind. But people stay because we are in love and because we don’t know what we’d do if we left….

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Evan,

Hoping you can give me some advice.  I dated this girl for 2 years and we broke up last year.  We broke up because she realized that she was no longer "in love" with me and that she felt there wasn’t enough of a spark.  Truth be told, there was another guy in the picture who she obviously had a bigger spark with.   This wasn’t my first breakup but it hit me really hard because I was so in love with her.  In my mind she was perfect in every way, (except for the part where she just wasn’t that into me).  I’ve been dating on and off the past year and I have two main problems:

1.  I’ve gone from being a serial monogamist to becoming completely commitment phobic.  The minute a girl starts to get serious with me, I want to run away. 

2.  I compare every girl to her and all I see is flaws in other people.  I keep waiting to have that "feeling" I had with her, because I’m scared that without that feeling, I will not be able to commit.

I’m worried I’m never going to get over this.  Any help is much appreciated.

Ken

I would be much more concerned with your second problem than your first.

Your first issue is that you’re commitment phobic. This is a common problem, one that is usually remedied by falling in love with someone. Once you’re crazy about a girl, you won’t have to think twice as to whether you want to be in a relationship with her. Which brings us back to your second problem:

I compare every girl to her and all I see are flaws in other people.  I keep waiting to have that "feeling" I had with her, because I’m scared that without that feeling, I will not be able to commit.

Let’s take these assertions line by line.

I compare every girl to her and all I see are flaws in other people.

Yeah. This isn’t good. Because it’s not real. It’s a rose-colored view of your ex, one that you’re having a hard time letting go of. Do yourself a favor and think of the things that you didn’t like about your ex. Now, I understand that she broke up with you, so you never really developed a chance to hate her. But that doesn’t mean she’s perfect – not by a long shot. Her main flaw, of course, is that she didn’t want to marry you. And any woman who doesn’t want to marry you isn’t really a very good choice for a wife. There are probably many, many more flaws that you glossed over due to your passion for her.

Being “in love” does this to people. In fact, Helen Fisher theorizes in “Why We Love” that being “in love” may be an evolutionary function that causes irrational thinking. In other words, in order to commit to something as irrational as monogamy, we’d sure has hell BETTER be blinded by love. Of course, that blindness wears off, which is why, when you talk to older couples who have been married for 30+ years, they’ll almost always tell you some version of “It’s hard work/We’re really just best friends/We know how to communicate and argue well/We support each other when it’s tough.” Etc, etc….

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My fiance of one and a half year will not commit to a date. He has postponed the wedding once (due to a very real financial crisis). We agreed on a timeline for us to set the next date and he is stalling again.

I want to be proactive about this but I don’t want to force him into a wedding he doesn’t want. We will have been together for 7 years in Jan 2008 and I know he loves me but is he waiting for the second coming to fix the date?

Sheena

Dear Sheena,

First of all, I want to acknowledge you for writing to me regarding such a sensitive topic. You’ve invested a lot of time with this guy, and I don’t want to gloss over your very serious issue. But it seems that since we can all be a little too close to our own problems, it might be easier if I give you one of mine to solve. The topic is a little touchy, so be gentle with me, okay? Okay.

So…

Dear Sheena,

My girlfriend will not give me oral sex.

She really loves me and said that she will one day be interested in performing it. It just hasn’t happened yet.

I try not to bug her too much about it because I don’t want her to feel pressured. But I’m beginning to think that, at this pace, I might never get sucked off again.

I know it’s possible to have a relationship without oral sex, but regular hummers are something I’ve always dreamed of. I’m not sure if she’s afraid of penises, had a bad childhood experience, or is just shy, but, after seven years of dating her, I’m starting to feel like a blue-balled chump.

What do you think I should I do?

Evan

First, a few things to note:

Marriage is more important and high-stakes than blowjobs.

My girlfriend and I have been together for 11 months, not 7 years.

She would not be my girlfriend if the above problem were true.

Despite the jokes, Sheena, I really, truly believe that our disparate situations have the same exact solutions.

Simply put, if you and I are not satisfied with the status of our relationships, we must have authentic conversations with our partners about how they’re not living up to our needs and expectations.

And if our partners tell us that things will change but they don’t, we’re faced with two choices:

Stay or Go.

That’s it. Two options. Nothing else.

By staying in a relationship that’s not meeting your needs, you become an enabler who allows your commitment phobic boyfriend to take advantage of you. And by threatening to walk and not walking, you establish yourself as a powerless victim and a doormat. That’s where you’ve been for seven years and that’s where you’ll be in seven years unless you do something differently. ‘Cause clearly, he’s in no rush to change….

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