I am dating this guy I really like. We have been dating since November of last year. 

We both believe in being up-front about things so he made it a point to tell me he wanted to take it slow because he has rushed into relationships in the past. We do have sex and it is great!

The main issue I have with him however is that he talks about his ex-girlfriend a lot; I feel like he is still hung up on her. She is a drug user and he knows he’s better off without her, but is still drawn to her. Should I bail on this relationship or talk to him at length regarding this issue?

Lerene

Dear Lerene,

You’re probably asking the wrong person.

I’m serious.

I’m one of those people who doesn’t see anything wrong in dredging up the name of ex’s for one simple and obvious reason: THEY’RE EX’S!!! There’s a reason I’m not with them and whether they dumped me or I dumped them, it amounts to the same thing: the case is closed.

And if I’m in a committed relationship and I want my girlfriend to really understand me, she needs to hear my crazy stories. This is my history, this is my rocky path, this is my life. The mere concept that I shouldn’t mention how crazy this ex was, or how devotedly misguided I was to another ex, is silly. But again, I’m not pining for them, putting them up on a pedestal, or talking to them four times a day. I’m sharing a very important part of my past – like talking about the way I was in high school, or my deceased father. These are the facts; I hope you choose to accept them.

To my girlfriend’s credit, she is a virtual Rolodex of Evan’s ex- stories. And it doesn’t faze her in the least. Because she knows it has nothing to do with her. And I know – when she gets emotional or vulnerable when sharing the pain of her failed marriage – that it has nothing to do with ME. She doesn’t miss her ex-husband. She misses the innocence, happiness and security that she felt when she was in that relationship. As a result, I do everything I can to make her feel special – including not getting jealous if she talks about the good times she had before the marriage fell apart.

While it may not feel good to know that your guy has latent feelings for someone else, as long as you don’t think he’s going to act on them, you should probably get over it.

This is all about removing your ego from the equation and looking at the facts in front of you. You didn’t give me many details so it’s really up to you to decide:

Is he talking about her because he wants her back? Or is he saying that he really cared about her, but she was fatally flawed? Because those are two different things. While it may not feel good to know that your guy has latent feelings for someone else, as long as you don’t think he’s going to act on them, you should probably get over it.

Dear Evan,

What’s the truth? Should women ask men out on first dates? Is it true that a man is "really not that into you" if he’s not asking you out?

Thanks!

Danielle

Dear Danielle,

You asked me a question, but you really asked me two different questions which have two different answers:

1) Should women ask out men on first dates?

No. No, they should not. Women asking men on first dates can be taken as aggressive, desperate, and masculine. At the very least, it can signify a loss of power. So I wouldn’t recommend that you ever utter the words, “Would you like to go out with me?” to any men.

This doesn’t contradict anything I’ve said before, because God knows, I’m not an advocate of women acting like helpless shrinking violets. Not at all. But there’s a difference between asking a man out and getting a man to ask you out. I vote strongly for the latter.

Women asking men out? No.

Women using all their feminine wiles to get men to ask them out? Yes.

So let’s get this straight:

Women asking men out? No.

Women using all their feminine wiles to get men to ask them out? Yes.

So what are these feminine wiles of which I speak? Besides your everyday, run-of-the-mill flirtation, there are TONS of things a woman can do to aid in her own dating process.

Let’s say you’re at a party and you see a cute guy across the room. Your friend tells you to go up and ask him out. But you’ve read this article and you know that he probably won’t respond to such a direct approach. What are you gonna do? How can you take action to make HIM take action?

Well, you can click here to see how I answer it in a video clip (about 4 minutes in) – OR you can keep reading…

So, if you see a man  you want to meet, how can you meet him? By putting yourself in the position to meet him. You can cross the room, park yourself seven feet to his diagonal, turn and smile. Now that he’s in your line of sight, he has an opportunity to make eye contact with you. And when men make eye contact with you when you’re smiling, that’s their invitation to come over and introduce themselves.

Result: Woman takes action. Man makes a move. Woman stays in control and keeps her feminine energy.

It’s important to understand this dynamic when we get to Danielle’s next question:

2) Is it true that a man is "really not that into you" if he’s not asking you out?

Yes. Kind of….

Continued on next page >>       Pages:   1 2

I hope you don’t find me to sound conceited or picky, but anyway I am hoping you can help me here. I am a 34-year-old single mom with a beautiful one year old daughter from a previous relationship that didn’t work out because my ex BF didn’t want the baby. I have never been married.

I am bothered by the fact that I’ve never been married. I SO desire to get married within the next couple of years or so, but I want it to be with the right person. I wish I was married about 5 years ago or so.  Like virtually all women, I would like to have my "princess day" of getting married before I go completely gray and I look too old. I am also very worried that if I don’t get married soon enough while my baby is young, she will never have a father figure in the picture whom she can comfortably bond with.

I believe I am reasonably attractive and on the "cute" side. I am five feet tall, a little over 100 pounds, and have very long dark hair.  But, to this day I have a hard time finding the right guy. I don’t feel any chemistry when I’m not with a guy I find equally attractive.  Sure, of course personality counts, but I just don’t feel comfortable with kissing a guy whom I don’t find attractive.

To sum things up, over the years I’ve found that the guys who are interested in dating me are either too "geeky" looking and unattractive, too old, or, if they ARE my age and I find them attractive– they don’t seem stable in life and don’t have a good job OR they’re just plain conceited jerks (like my baby’s father). I’m not kidding. I’ve been trying online dating with several different sites, but that hasn’t worked out for me.

Why am I having such a hard time in finding someone who is mutually interested in me whom I find attractive, who holds a steady decent job AND has a decent personality?  I don’t think I’m asking for too much here, or am I? Should I force myself to be in a relationship with someone whom I don’t find terribly attractive and I don’t feel any chemistry with (whom I just don’t want to be "intimate" with?).

Paula

Dear Paula,

We covered this recently, but since you speak for a lot of women out there, I wanted to try to tackle your question in a slightly different way.

First of all, I want to validate all of the women who feel just like Paula does. I know it’s not always easy to hear the other side of things – or even consider that there IS another side of things – but we’re here to try to get down to a core truth. This isn’t about right and wrong; this is about effective and ineffective. If your goal is to get married and find a father for your baby, you always have to keep that in mind.

If you want someone stable and kind and attractive and tall and personable and age-appropriate and financially well-off, and you can’t seem to find him? Maybe you need to compromise on SOMETHING.

And I think that’s where the Lori Gottlieb critics went a bit astray. See, if your primary desire is to lead an exciting, passionate life, then, well, you go, girl. But if you want someone stable and kind and attractive and tall and personable and age-appropriate and financially well-off, and you can’t seem to find him? Maybe you need to compromise on SOMETHING. You can transpose the world “settle” for compromise, if you like, but we’re talking about the same thing here: giving up one thing to get something else….

Continued on next page >>       Pages:   1 2

Hi Evan.

I’m 30 years old, European, attractive, tall girl. I have a strange situation. The same scenario happened to me at least 5 times in the last few months. I go on a first date and I can tell for sure that a guy is interested in me. He invites me for drinks after we had dinner and he makes plans for our future dates by saying "I should take you to this great restaurant or we should go to see this play…" And then I never hear back from him. My guy friends say that I just intimidate men or that I just meet the wrong guys and all they want is just sex. What do you think?

Thanks,

Alena

Thanks for the transcontinental note, Alena. Although I’ve answered this question before, it’s still a timeless one.

You have fallen victim to the most common mistake women make in dating. It’s the hardest message to hear, so please don’t shoot the messenger.

Mistake #10: Thinking That Your Great Date Actually Meant Something

Have you ever had a man say how much he likes you, how sexy you are, and how he’s serious about finding a long-term relationship? Ever have an amazing date where the chemistry was great, the conversation flowed, and you hooked up with him afterwards?

Have you ever had a man do all of these things and then NOT call?

No, you’re not crazy or delusional.

Your mistake is thinking that what a man says on a date actually means something. It doesn’t. It means he’s being in the moment. So don’t put too much weight on a great date. The only way you can tell how a man REALLY feels about you is by how quickly he follows up for another date.

I walked her to her car and we made out for ten minutes, standing on the street. I never heard from her again. 

One of the first JDates I ever went on was back in probably 1999. She was a doctor, went to Harvard, came from a similar East Coast family. We went out for drinks at a local hotel bar and stayed out until the place closed at 2. I walked her to her car and we made out for ten minutes, standing on the street.

I never heard from her again.

What does this MEAN?

Nothing. Absolutely nothing….

Continued on next page >>       Pages:   1 2

Over the last several months, I have dated 3 men (not simultaneously) that I met on Match.com. They all seem to have one thing in common:  after 2-4 dates, they like to touch base with me during the week by sending me text messages to my cell phone! Although I appreciate them thinking about me in the middle of the day, if we have gone out on several dates, at what point is it appropriate to expect a 5 minute phone call a few times a week? Is it too early in the dating process for phone contact? How are you supposed to progress the relationship if you never "touch-base" by actually speaking to one another? Is this typical of people you meet on line? Or, am I just old fashioned (39) and not used to this new aspect of dating?

Rikki

Dear Rikki,

You struck a chord with this email.

I HATE text messaging. I think it should be used exclusively for only a handful of things:

Letting someone know that you’re lost or running late.

Telling someone where you’re located in a crowded theater or bar.

Writing flirty or dirty notes to be provocative and naughty.

Everything else should be banned. I mean, email is bad enough. And I say this as a guy who lives by email. But anyone who’s ever used it knows how conversations can easily take a wrong turn. There’s no context, tone, voice, or facial expressions to modify your message. The next thing you know, you’re having a vicious argument that could have been easily avoided in person. Plus you have a transcript to commemorate it!

Texting is ten times worse. You’re encouraged to misspell, you’re discouraged from saying anything deep or meaningful. Essentially, texting is emailing for the lazy, illiterate and mobile. You send a text when you don’t want to talk to someone, but you want to let them know you’re thinking of them. And what can be more flattering than conveying, electronically, the idea that you DON’T want to talk to the woman you’re courting? Essentially, guys across America are saying, “Hey, babe. You’re not important enough to get five minutes of phone time. Please accept this weak form of communication and allow me to keep on sleeping with you.”

Guys across America are saying, “Hey, babe. You’re not important enough to get five minutes of phone time. Please accept this weak form of communication and allow me to keep on sleeping with you.”

And as long as you let them do it, they will continue to do it. Because texting is only enabled by the person who writes back to the text. If you don’t respond to texts, guess what? You’re letting him know that it’s a poor way to reach you.

Understand this about men: they will usually do the least that they can to maintain their relationship. So if he can text you at 11pm on Friday night after a week of silence and charm you with something like: “ UR 2 hott! Cum over now?”, well, you get what you deserve. But here’s the real problem: there are women everywhere who are complete suckers for this crap. Maybe it’s a low self esteem thing, but as long as some desperate girl lets him get away with it, he’ll always have a low-maintenance sexual outlet. Therefore, he’ll never feel the need to do all the heavy lifting of relationships such as “calling” and “dates”….

Continued on next page >>       Pages:   1 2

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 every come from women asking men out. Still, 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….

Continued on next page >>       Pages:   1 2

Hi Evan -

Really enjoy your blog. I found out a few months ago that I have herpes. After going through the normal flip out and that my dating life would now consist of Ben and Jerry’s and DVD’s every Saturday night, I’m ready to get out there again.

I have gone through "the conversation" a million times in my mind. I have seen men post on various dating sites where they come right out on their profile stating they have herpes. And before I found out about my little gem, I would immediately think, "not in my backyard". I think that is a TMI on a profile. I thought that if I meet someone, and there seems to be some sort of vibe, I would have the talk pretty quickly, possibly even the first date. And I wouldn’t be dramatic, just simply say, you need to know something, I have herpes. I control it with medication, but no matter how you slice it, it is what it is.

There are "herpes sites" but they kind of creep me out at this point.

I have enough common sense that I wouldn’t casually mention this as we are flinging clothing all over the room.

What are your thoughts? Is there a "right time or wrong time" to have this discussion?

If ok, want to jump on my soapbox for a second, if anyone reading this has herpes, do the right thing, let people know. One of the most difficult things I had to do was call former boyfriends I may have exposed (think it was dormant in my system for quite sometime, I honestly did not know). None of these guys started screaming at me, they THANKED me and said they would get tested - none of them had it -YAY!!!!

This is forever, don’t make it forever for someone else - have "the talk".

Thanks Evan, happy new year!

Jen

Important question, Jen. And while I’m not an expert in herpes, per se, I do know a number of people who have it, and continue to lead rich, happy, limitless dating lives. So don’t worry. It’s all gonna be okay.

I do know a number of people who have it, and continue to lead rich, happy, limitless dating lives. 

I think all the readers should take a second to put themselves in your shoes for a moment. Because one second you’re saying “No way” to a guy with herpes, and the next, you’re praying that a guy doesn’t judge you for this one minor thing.

And let me be clear, it IS a minor thing.

According to Herpes.com, 50-80 percent of the American adult population has oral herpes. Ever had a cold sore? Congratulations. You probably have oral herpes. As far as genital herpes goes, we’re talking 205 of the population. That’s 50 MILLION people, a majority of whom don’t even know they’re infected. The scariest part of this whole thing is the staggering ignorance about herpes – a disease that undoubtedly affects someone that you know.

Don’t think so? Well, let’s just say that I have close friends, clients, and ex-girlfriends who have genital herpes, and none of them are traumatized, hospitalized or ostracized because of it. So let’s get past that.

Just know that if you have the disease, you may be entirely asymptomatic, which would mean that you could potentially transmit it without knowing. And if you do have symptoms, they are easily controlled with the use of drugs. The question is how do you explain this to someone else who is freaked out by this kind of stuff?…

Continued on next page >>       Pages:   1 2

Evan,

Over the past couple of weeks I’d been e-mailing a woman who initiated contact with me. It was pretty apparent from the timing of the mails that she didn’t always have access to the web which I, being in IT, do.

We had our first conversation on this past Tuesday night and it went well. We have a date scheduled for Saturday evening to get drinks. During the call she gave me her regular e-mail so we wouldn’t have to work through match. The next day I sent her a very short e-mail mostly to answer a question she had that I didn’t have the answer to Tuesday night. I also said I enjoyed talking with her. She responded that she enjoyed the conversation and was looking forward to Saturday.

Now, I thought it would be appropriate to speak one more time before Saturday. So yesterday (Thursday) I sent an e-mail asking if it would be better to call that night or Friday. That’s all the mail said. I didn’t get a response yesterday so I didn’t know if she got the mail or not. I posted this information on a forum I use - and while a couple of women said I should go ahead and call, several others said that I was appearing needy, that I shouldn’t have asked when a good time to call would be. Some even said that I shouldn’t have had any more contact until Saturday at all.

Now, I’ve heard plenty of horror stories about the guys that call several times a day but I don’t think I was approaching that territory. As far as I was concerned, I was being considerate in asking when a better time to call would be. Did I show weakness? Neediness? Expose my throat?

Has it really come to this, that it’s not just "don’t be a stalker" but that any sign of showing you want to talk to the person is a sign of weakness and grounds for elimination? If so, why do we have the audacity to wonder why so many of us are still single?

Thanks,

Markus

Dear Markus,

Thanks for the note. Since you’re a regular reader and commenter, I wanted to get back to you as quickly as I could.

Anyone who’s been here before knows that I never ever EVER validate the person asking me a question.

• If a woman says that her boyfriend is a jerk, I’ll ask why she’s dating a jerk.
• If a man says that women are fickle and judgmental, I’ll ask if he’s fickle and judgmental.

I think there’s nothing to learn from pointing fingers at the world’s injustices. The real power comes from seeing the world clearly, assessing your role in why things happen, and deciding if there’s anything within your power to alter the future outcome….

Continued on next page >>       Pages:   1 2

My question is this: is it wrong to date someone who is extremely similar, on paper, to the last person you dated? 

Would most people be uncomfortable to hear that their boyfriend/girlfriend’s last significant other was a clone of themself? 

I’m about to date a girl who, on paper, is A LOT like the last girl I dated. I have a great deal in common with this girl, just like I had a lot in common with the last girl, but I’m worried that I’m not liking this new girl for herself. I think this new girl is the recipient of feelings I developed for the last one.

Mike

Dear Mike,

I’ve often said that we are the sum total of our experiences.

And when we look back on our lives, we can see patterns in our choices in partners. Often, we get it wrong. Sometimes, with practice, we can even get it right.

So the more salient question that I’m going to answer for you isn’t whether there’s anything wrong with dating a girl who is a lot like your last girlfriend. (There’s not. Case closed.)

What IS interesting, however, is whether these repeated patterns of girls are GOOD for you. That’s an entirely different story, and one worth exploring.

See, it’s not that your question isn’t relevant. It’s that, truly, if your last girlfriend was a wonderful person with whom you had an amicable breakup, there are no real warning signs that this “type” is wrong for you. Thus, finding a woman with similar characteristics on paper is not only fine, but probably a decent idea.

If your last girlfriend was a wonderful person with whom you had an amicable breakup, there are no real warning signs that this “type” is wrong for you.

As always, I speak from experience. For years and years, I chased the holy grail of East Coast Jewish intellectuals. I found that as much as I craved their company, they were usually too similar to me. They may have been interesting and successful, but they were also often hard-driving, opinionated, and selfish. Last year, I dated a woman who was the opposite. She was considerably younger. She didn’t have a big career. She was interested in doing everything I wanted to do, just so we could be around each other. With her big smile, generous heart, and accepting ways, she made me want to be a better boyfriend. We only broke up because she wasn’t seasoned enough – I didn’t feel like I was learning from her, although I’m sure she’s going to be an amazing woman in about five years.

Cut to six months after my breakup. I meet another woman with the same exact qualities – except this woman’s turning 38 tomorrow. Ten months later we’re still together. Have I fallen into a trap? No. I just discovered that it’s more important for me to be with a woman who makes me feel good than to be with a woman who fits that mental checklist we all have….

Continued on next page >>       Pages:   1 2

Dear Evan,

Why do dating experts for men teach them how to get the hottest women possible? Unlike women, they are rarely told to date someone they might not find attractive at first because she might grow on him. As an average looking woman (I am fit, well-groomed and fashionable, but I know that I am not a bombshell. I don’t make people gag, but I don’t turn heads either.), I feel that no man is going to find me desirable because all men feel that they deserve and can get the hottest woman out there. Just where does that leave women like me? 

Tia-Maria

Dear Tia-Maria,

Thank you, thank you, thank you for asking this question. A few months ago, I promised to write a post about shallow men, and this note from you is the perfect excuse.

First, a story:

When I started writing Why You’re Still Single, back in early 2005, I was working with a different woman than my eventual partner, Linda Holmes. This original partner was a noted matchmaker who brought a certain credibility to my pet project – she’s experienced in her field, she’s telegenic, she knows plenty about single people, etc.

One of the first chapters I completed was called “The Beauty Myth Is Not a Myth”. It didn’t necessarily debunk Naomi Wolf’s seminal work, but it did establish one very important concept that women need to understand: Men are as shallow as advertised. And while women can beat their heads against a wall, wishing that this were not true, they’re fighting a real losing battle if they expect men to stop worshipping at the altar of beauty.

Like much of my advice, it can rub a woman the wrong way. But I wasn’t condoning the behavior, I was merely reporting it. This is what men do, whether we like it or not. Yet my writing partner felt so unnerved by my stance, that her version of the “Beauty Myth” chapter only served to contradict everything I had written.

She mentioned that she was in the business of connecting souls.

She stated that as men mature, they learn to appreciate inner beauty.

She encouraged women to hold out for the kind of guy who isn’t as focused on the outer packaging.  

That’s when I fired her from the project.

I tell this story not to make myself look good (clearly), but because I refused to put out a book that gave bad advice. And make no mistake about it – telling women to hold out for men who don’t care about looks is BAD ADVICE. Why? Because men like this are as common as Halley’s Comet….

Continued on next page >>       Pages:   1 2 3