WTF Wednesday: I’m crazy about him but he’s intimidated by me

single mom advice


Dear Emma, 

WTF?! I’m a single mom who has always been ambitious — but since my divorce 10 years ago my career really took off. Today I’m killing it as a Fortune 1,000 executive and despite your bashing of corporate jobs, I really love mine. 

Needless to say, I intimidate men — especially those I date. In fact, I was the breadwinner in my marriage and my husband told me flat-out that he couldn’t deal with it. I don’t have trouble meeting interesting or successful men and have had some short-term relationships over the years. But when it comes to long-term relationships, guys tend to shut down and freak out — even when they make more than I do. 

Case in point: I am currently seeing someone I really like, and sense a lot of relationship potential. He is a brilliant entrepreneur who is currently running a startup and launching a second. I’m pretty sure he doesn’t earn as much as I do, but we are clearly peers intellectually and in business — as well as in things like cultural tastes, values and all the good important stuff. Plus, I think he is really hot.

We’ve been seeing each other casually (but not yet sleeping together) for the past few weeks. We have really great conversations and enjoy going to the same restaurants and concerts. But I can tell he is really nervous around me, avoiding eye contact and acting shy sometimes, and when it comes to talking about our careers, sometimes he acts really interested in my work and says such flattering things about how pretty he finds me, and how amazing I am for my career while being a mom — it is music to my ears! But other times gets a little shifty-eyed when I talk about my accomplishments. I find I started to hold back and downplaying things that may hint at my success and act overly enthusiastic about his. 

The thing is that I don’t see myself as more successful than him even though I probably make more money — which I don’t care about at all! There is so much potential for this to grow into something meaningful but I worry that this will be a repeat of my past relationships — lots of potential and chemistry and ultimately a petering out when he faces the possibility of being with a woman like me.

Alpha woman in Alberta

Dear Alpha,

I am so grateful for this message. A lot of readers here will so relate — as do I. So my message to you is one part helping, one part therapy for me (cuz it’s all about me!).

When I hear anyone make broad generalizations about others, a red flags shoot up. ” I intimidate men — especially those I date.” I don’t doubt that some dudes are not sure how to date a successful woman. But if you keep experiencing the same thing again and again, there is just one common denominator: You.

I worry that you have not moved past your ex-husband’s insecurity around his success (because the problem was him — not your success!) and the role it played in the dissolution of your marriage. He was one man, and that was one relationship. There are other men and other ways of being with them. I firmly believe that the vibe we throw off is a giant, powerful force in who we attract to our lives and how those relationships play out. You have control over that vibe. You are attracting men who are just like your husband — men who are insecure with themselves, and therefor intimidated by you.

Also-slash-in addition: You may be inaccurately perceiving these men’s disinterest as intimidation. Maybe they are not into you for other reasons. Or maybe they actually really dig you, and you pre-emptively call things off for fear of being hurt again. This is so normal (and familiar!). It is also within your power to change.

Here is what I want you to do:

First, identify some happy marriages you know where the woman is a professional success — someone you admire and respect. Spend time with those people. Dissect how they tick — how they interact and share housework and talk about business. Surround yourself with the type of relationship you desire. See that it is possible. Learn the mechanics of those partnerships.

Second, give this guy a shot. It has only been a few weeks, and I agree — it sounds like the making of something special. Do not despair quite yet.

Third, turn it around. You already have established a certain, albeit awkward, flow with this man. That is difficult to undo. But it can be remedied.

Your next step:

Let him fuck you. Notice I didn’t say fuck him. No. Let him take over. Be the man. That means you are the woman.

What does that mean? The next time you are making out do not initiate a single thing. Every single step of intimacy is up to him. That does not mean you are a limp washcloth. That means you follow his lead. Is he unsure? Stumbles? Tell him how hot he is. How big. How much he turns you on. Mean it (because you do). Want him (because you do). Allow him to dominate in a way that is impossible for you to compete with.

Because you are the woman. And he is the man.

And that is what it is all about anyway.


Emma Johnson

Emma Johnson is a veteran money journalist, noted blogger, bestselling author and an host of the award-winning podcast, Like a Mother with Emma Johnson. A former Associated Press Financial Wire reporter and MSN Money columnist, Emma has written for the New York Times, Wall Street Journal, Forbes, Glamour,, U.S. News, Parenting, USA Today and others. Her #1 bestseller, The Kickass Single Mom (Penguin), was named to the New York Post’s ‘Must Read” list.

Emma regularly comments on issues of modern families, gender equality, divorce, sex and motherhood for outlets like CNN, Headline News, New York Times, Wall Street Journal, Fox & Friends, CNBC, NPR, TIME, MONEY, O, The Oprah Magazine and The Doctors. She was named Parents magazine’s “Best of the Web,” “Top 15 Personal Finance Podcasts” by U.S. News, and a “Most Eligible New Yorker” by New York Observer.

A popular speaker, Emma presented at the United Nations Summit for Gender Equality. Read more about Emma here.

20 thoughts on “WTF Wednesday: I’m crazy about him but he’s intimidated by me

  1. So the answer to all this is for her to act like a slut let the guy f—k her ? That’s part of the reason why women have such a hard time finding a good guy . Guys know these days that they can get what they want out of a woman without committing. Then as soon as she gives it up they’re gone . I think women should have more respect for themselves , and when they do they’ll start receiving more respect and commitment from men. When you have sex with someone you become one with that person . No one should be sleeping with every person they’ve ever dated .

      1. I liked that particular suggestion! As a strong woman who has a crazy (and many times unhealthy, thanks therapy!!) need to take of myself and NEED NO ONE…this is sound advice. It takes work for me to allow people to help me or “take care of me”. I take charge everywhere in my life, the bedroom is no exception. In my current relationship, my boyfriend loves that I’m “one of the guys”, and I certainly don’t downplay my accomplishments . He works for me, because he is probly the most laid back person I’ve ever met. And me…well…I’m kind of like an espresso shot. That being said, I let him do things for me. Pay for the sitter, dinner, get out and pump the gas. I let him drive! I always drive, this is a very, very big deal! I literally had to sit on my hands in the beginning to let him be this way. I still buy him dinner or bring over his favorite drink, cook him his favorite meal, but I don’t argue when he offers. As far as the bedroom…while I throw myself at him plenty, he’s the boss. It’s. Freaking. Awesome.

        1. I so identify with everything you said. There is so much pressure we put on ourselves to do it all — but it gets to be a point of ego and control and defensiveness at some point. You simply can’t be close with people — lovers or otherwise — unless there is a degree of mutual dependency. Also – it feels good to help. Allowing others to help and care for us is a gift to them, too.

    1. This is your opinion, Emma has hers. Which, I agree with. Being single and having sex in my mid…ok, late 30’s, has been such an empowering and awesome thing. I’m not self conscious, I know what I like, therefore it’s amazing. Totally different from in my 20s. People can explore their sexual needs. As far as “Guys know these days that they can get what they want out of a woman without committing”, we are all adults. I’m pretty sure only boys in highschool and college pull this crap. As adults, we can connect on a sexual level without total commitment and explore weather there is a connection. And a sexual connection is hugely important. I remember really liking this guy I dated before my ex husband. I waited awhile to have sex with him. He ended up being terrible in bed. I wasted alot of time, because we just weren’t compatiable sexually. I’ve never in my life heard an adult male say “You know, I would have committed if she just made me wait to have sex.” Uh no.

  2. Seriously? SERIOUSLY? Tell him how big he is? THIS is what we’ve come to? You have depressed me so much, I can’t even tell you. And you’ve missed the giant red flag in the letter — maybe she just talks about herself too much and never lets the other person speak. Maybe she’s just really boring.

    1. Hi “Squanky” (can a person named Squanky be depressed? Is that possible?) — I addressed in this post that she may be the problem. Happy reading …

    2. Exactly what I was thinking! I was reading all the comments hoping that someone else picked up on that. I’ve noticed that I am guilty of talking myself up during a date. I was seeing an Irish girl and she said “you’re doing that Canadian thing, where you brag about how awesome you are”. Really I was just trying to convince her that I am a worthy addition to her life but at the end of the day I cringed when I thought about how much I bragged…. made it seem like I was in love with myself. My point is, maybe he looks away because he feels embarrassed for you when you start to brag.

  3. I guess everyone here is ok with sleeping around. Our society has taken a step backwards . We live in a world where women say they don’t want to be an object to men, yet they contradict that by sleeping with every guy they date.It’s naive to think you can give a man whatever he wants and he really respects you. Feminism has not changed the way men think. People do have sexual needs but that is a privilege to be satisfied within the bonds of marriage . Sleeping with several different people is why so many people can’t find satisfying love. Good sex comes with love . You should love deeply first then sex. The way people do things now makes it to where they are too focused on sex and comparing this or that guys sexual technique to the guy before . If you’re in love you are compatible sexually . People just don’t know that because they’ve slept with too many people to figure it out. A strong foundation for a good relationship is mutual love and respect first. I’m not saying this in judgement . I made the mistake of getting pregnant years ago before I was married but I’ve since repented . I’m saddened to see how much the world doesn’t realize how sacred, holy , and pure sex is and that it’s not meant to be given to several people. We are not meant to become one in body and spirit with everyone we date. Sex isn’t purely a physical act but a spiritual one. It is a gift . I’m saddened to think the best advice this woman could get here was to let the man sleep with her so she could keep him. Women keep sleeping with guys to keep them and most of the men keep leaving them anyway. Same reason why a lot of young girls keep ending up pregnant . The same theme keeps repeating itself . I wish more people could know Jesus and see the value and freedom in purity .

    1. Obviously we have different opinions on sex. I don’t believe it to be only given to one person. I do believe that with sex, comes great responcibility. Pregnancy, disease. You need to be educated. Also, very honest with yourself about how you feel about sex. You clearly believe in only marital sex. So you don’t have casual sex. I’m ok with casual sex. Is it better than being in love and having that deep, spiritual connection sex…depends on my mood. Neither of us are going to change each others minds. But I completely disagree with your blanket statements that premarital sex is responcible for relationship demises. Also, I was really had fallen in love with the guy I spoke of above. He really was terrible in bed. We did not connect on that level. It was devastating. Thank god I didn’t just marry him. I would have been miserable. I do believe it is special, and when you are in love…it’s can be amazing. I want to disguss my disagreement with you on these points.

      1. Emma was not suggesting to sleep with this man to keep him. That was not what I was getting out of it. She was suggesting that she let him take the lead. Be the alpha.

      2. Girls get pregnant because they aren’t using birth control. This has been happening since the dawn of time. You know who got pregnant in my all girl private catholic highschool? The girl who knew the least about birth control. She somehow thought you couldn’t get pregnant the first time. Wow. Teen births have been on the decline since 1990. I believe education has helped with that. I will have a very frank and educational talk with my 3 children about sex and birth control. Granted, there would not be any UNWED teen pregnancies if people waited until they got married. But, I believe we’d have teens running off and getting married and have an even higher divorce rate.

      I respect your beliefs for you and your life. It’s just not how I believe. Anywho, I’m going to finish up at work here, and spend my first weekend that my ex is in town and has the kids, having awsome, mindblowing sex with my boyfriend. Well, inbetween marathoning netflix and waiting for the walking dead on sunday!! We might even go out…gasp!

      1. Hopefully when it comes to your kids that you aren’t saying, “Do as I say, not as I do”. I always wondered what promiscuous women teach their children. So do you have sex with other guys while you date your boyfriend? If you don’t believe in only having sex with one person how long before you dump him. Unless you are a cheater. And congratulations on contributing to more out of wed lock births. This whole nation will be full of bastards in the future.

        1. If you read my comments, I never once said sleeping with more than one person. I just said out of wedlock. I don’t cheat. I’m a very monogmous person. I’m not a do as I say, not as I do person. I will actually educate my children on sex and reproduction. Have a nice day!

  4. When you rub your success in someone else’s face you might as well take a big pile of crap and shove it into their face. She is obviously doing this. I don’t care about money because I make a lot of it. She seems arrogant and obnoxious. Maybe she should try being a woman.

    I don’t understand you Emma. You wrote a whole piece about breadwinning wives and all the problems it causes and then here you say that her previous husband was insecure and it’s his problem that he couldn’t deal with her success. From your article you should already know a lot of men can’t deal with it. And a lot of women can’t deal with it either. And as you said that relationships where the breadwinning wife earns more it is more prone to divorce. And here is a classic example of that. She probably made the guy feel like a loser and emasculated. And he hated it. And who divorced who? She probably resented him too. Breadwinning wives are trouble.

    And she is a divorced single mother career woman? Run buddy. Get the hell out of there.

        1. LMAO. No!! That wasn’t me, merely someone else who makes similar points. I’ve just been off cooling down for a while. :)…and working working working….

          And Marissa, I don’t believe you are a cheater at all. On this point we agree.

          Actually, my first thought on the article was to advise that if she gets serious with guy – meaning marriage – she better get a pre-nup to protect herself financially. I told a guy at work today if I ever come into the office and tell my co-workers that I’m getting married they need to call the authorities as my fiance’ will most certainly be putting something in my food and drink to drug me to such stupidity. Ha!

          Honestly, I fully agree with casual sexual relationships, and, mostly (I suppose there is the very rare exception….but that’s the hopeful side of me that rarely appears.), think all men and women should stay out of serious relationships. Although, if I am involved in some type of FWB situations I generally do stay monogamous as I simply don’t have time to bounce around if I’ve got some “trim comin’ in” all regular. Obviously, if 70 percent of people in “monogamous” relationships cheat, why get one’s hopes up trusting anyone? Trust short-term I say, until it gets old.

          As for “Alpha”, in my serious relationship days I wouldn’t have had much of a concern if she earned more than me (and my own ethics would never let me take financial advantage of the situation I would add.) I think any guy feels some concern that a more successful woman may think he’s not “up to snuff” due to his earning power, and most women’s actions in my dating life only reinforce that most women aren’t concerned about a guy’s work ethic, rather they are concerned about what’s in his wallet. So, a guys “intimidation” in the matter is to be expected.

          In her Alpha-ness, I wonder if she puts on too strong the “Alpha” airs. I know in my serious relationships, I’ve always been a “helper” type, liking to identify areas where I can show my willingness and ability to assist. I don’t think all guys are like this, but perhaps at least in some situations it’s less the financial position of Alpha, and more the day to day “powerful woman” she exudes that may come across as lacking sensitivity and affection – the Glenn Close stereotypical characters as high-powered, executive bitch comes to mind. So, Emma’s advice to let him “fuck” her literally and symbolically isn’t totally off the wall. It may be that the guy needs to feel “needed” on many levels as a guy, and she jumps in to control too much.

          “identify some happy marriages” – LMAO……Sure, good luck identifying “some happy marriages”. She better just look for one or two; finding “some” is a real stretch. I can think of about three couples out of dozens who I truly believe to be in “happy marriages”, and only one is in step parent role.

  5. As a guy, this is good fucking advice. You want to get a man, do this. Why do some women have a problem being a woman when theyre dating a guy??? it baffles me. If you dont want a relationship, hire someone. If you do, wtf are you doing?

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