When it comes to dating I feel bad for men

 Oh man, you just killed his boner. Or maybe gave him one? I don't know. I give up. 


Who initiates the date? Should he make a reservation then tell her where to meet  — or ask her favorite spot? Offer to pick her up? If he confirms beforehand does he sound needy? What should he wear? Is dressing up for a date passee?

Is it too presumptuous to suggest a bottle? What about a nightcap? 

Who pays?

Who makes the move?

Brings the condoms? Goes down first? Gets on top? Gets off first?

Does he assume he'll stay the night? Call the next day (or text?)? Is an invite to see her four days later too soon? She is still on Match.com. What does that mean? If she doesn't respond after six hours does he ping her again? Friend her on Facebook? Pretend it never happened? 

And that is just the first week. When it comes to dating, the feelings have been the same since the dawn of humanity: thrilling, intoxicating, humbling and humiliating. But the rules of dating have changed dramatically in the past few years. The advent of online dating, social media and texting mean that decorum dictating dating code has been turned on its ear.

I should know. I date. And I often find navigating courtship rules to be an amorphous landmine. And I'm a woman – I'm not expected to lead the courtship ritual. But I am expected to set the gender rules, and I'm not sure what those are. Mayhem ensues.

For example — the last time I was single 12 years ago, if I was sleeping with someone and going on proper dates (plural) with him, I was not seeing other people. Today, everyone is a free agent until all parties explicitly agree otherwise. That is a real game-changer — a memo that has not been delivered to every newly single person.

Case in point: A couple years ago I was dating someone I really liked – someone who fancied himself quite progressive (I concurred). I had been out there for a couple years, getting acclimated to the new dating world. He was fresh out of the shoot. It was hot and heavy and I eagerly awaited his play for exclusivity while I keep seeing other people, even though I was nearly certain he was not (being that he was still playing under those old rules from the early aughts), and I was only interested in dating him. The affair imploded in a burst of electric confusion when, in frustration and uncertainty, I declared: “You know I'm seeing other people, right?”

His reply:

“I would be seeing other people too if I weren't so busy I don't like the idea of you seeing other guys I assumed you were seeing other people and you totally should!”

That conflicted responses is a perfect example of how men — especially progressive, feminist men like you and I date — want to do right by women. There is a sense in the world and dating especially that is full of man-hate. Women oft declare — unabashedly — that men are patently unfaithful, childish, unhelpful and, in general, douches. There is a lot of pressure for men to overcompensate for their gender's perceived shortcomings — warranted or not.

These men I date, they want to do the right thing by feminist women, but they're not sure what that is. Because we're not sure what that is. Since women set the gender agenda, guys feel pressure to follow our lead. It is reasonable for them to expect us to know if they should pay or stay. But, if you're like me, sometimes I really want him get the fuck out, but feel bad saying so. But if he stays and I prefer he call Uber and leave me to a good night's sleep, I will so not respect him. So sometimes I let him think it's his idea to go, even though I worry I hurt his feelings while he worries he hurt my feelings — which I feel guilty about, and I imagine he does, too.

That is only where the problem begins. Because, as I said, they follow our lead. Me? I like him to lead, and so do you. And men like to lead. But that makes us bonkers. The refuse-to-ask-for-direction thing? It drives women crazy. Guys like to feel like they know what they're doing, and women like guys who know what they're doing. And a man who knows how to handle things? Super sexy. A guy flubbing around, unsure? Not so much.

As we're are all struggling to figure out how to get what we need and want at work, in Washington and in bed, it is tough to define exactly what “being a man” means — just as we struggle to define our femininity — and feminism.  After all, no matter how often I've sat back in my chair when the check arrives, no matter how many times I write about my certainty that man should pay on first dates, regardless if I cringe when on that all-important first encounter he says, “I'll get this one and you grab the next one, OK?” or even when it is so clear that he feels amazing for treating me to theater tickets  — I still suffer a twinge of post-feminist guilt for not insisting I pull my financial weight at all times.

So if I'm struggling to sort this out, and he's struggling to do right by me, well, it's a case of the blind-leading-the blind. And he's in a shitty position, because there is no right answer. And I feel bad for him, because all he wants to do is to feel confident he is doing the right thing.

I also feel bad for me, because I want to be with a man who feels confident and I realize that I totally contribute to a whole lot of the contrary. And I also feel bad for me because I want to feel confident I'm doing the right thing, too.


About 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, Oprah.com, 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.


  1. DarthW on August 25, 2014 at 7:44 am

    I do agree that the dating world is completely a confusing mess. And while I like many of the equality considerations in feminism it has become a warped mess in our society because women want to select only those parts of feminism that selfishly benefit them, and use that “man-hate” to think men should take a back seat to women in all situations, as if because you push kids our your “jines” that you are somehow demi-gods; Barf.
    When I tried to be a nice guy, I would fall into much of the confusion you mention in the blog. The sad reality is that it’s easier to be a “bad boy” and avoid the whole mess. It’s a lot less pressure, a lot less confusing, a lot more sexually “profitable”, and I empty my wallet of money a whole lot less often.

    1) “Since women set the gender agenda, guys follow our lead.” – At one time, guys did. Many times now it appears to you as if we are, but in reality we are playing a game to get sex from you. We have no intention of getting entangled in the confusing molasses of a committed relationship with you to have you take our money from us. Only Poindexters still believe women truly set a gender agenda.

    2) “Today, everyone is a free agent until all parties explicitly agree otherwise.” – In my experience, women think they are “free agents” even after everyone agrees otherwise, unless somehow a single mom isn’t a “free agent” when she’s still boinking her ex-husband every once in awhile. Besides, in “Surrender to Marriage” the author admits that up to 60% of spouses – regardless the gender -cheat in a marriage, so how faithful should anyone believe someone they are simply dating is going to be?

    3) “he’s struggling to do right by me” – If a guy is struggling, he still believes in some sort of chivalry from bygone days. All men should just do what they want. No need to make the effort to be a decent human being when women are drawn to bad boys like flies to dog poo. In doing so, I get more sex than I ever did being that chivalrous nice guy and trying to do the right thing for her on a date.

    4) “There is a sense in the world and dating life especially that is full of man-hate.” – In men’s world there is “woman-hate aplenty” as well. The difference is that at one time most men didn’t fulfill the perceived reasons that so many had “man-hate”, we were decent, nice guys. Ironically, women were more attracted and sexual with the guys who portrayed those very traits they hate so much, so now more men do the bad boy thing. “Woman-hate” is a newer phenomenon from the male dating perspective which perceives women as selfish, entitled, scandalous, cheaters, and gold-diggers. And here the difference from women’s “man-hate” is that men’s “woman-hate” is, and has always been, based in reality and truth about women for the last 20 years.

    5) “I totally contribute to a whole lot of the contrary” – All women contribute a whole lot to the contrary. They think they are entitled to a knight in shining armor whose wallet they can invade whenever they want, meanwhile they want to act like a spoiled, selfish princesses who makes him the last priority – especially if they have children from another man.

    6) “And he’s in a shitty position, because there is no right answer.” – He sure is, but we’ve found the solutions to the problem: Be a bad boy, and get the sex you want. Be a bad boy, and don’t EVER commit to her. Be a bad boy, and get her to pay most of the time, so she gets no access to your wallet. A Poindexter puts himself in a shitty position because he tries to be that nice guy and naively believe that most women are still decent. A sensible man knows most women aren’t decent, so doesn’t give her any influence or “power” in his life.

    • Emma on August 25, 2014 at 8:17 am

      “In reality we are playing a game to get sex from you. ”

      Dunno – sex is very easy for people to find, regardless of gender.

      • DarthW on August 25, 2014 at 9:54 am

        That’s been my experience as a “bad boy”, but again, it’s all a game. When I was the nice guy all I was doing was spending money, and a few dates later I might get in her pants. Meanwhile, more than once she was giving it up to some other bad boy – or her ex husband – because we hadn’t had that “exclusivity talk” that is so much bullshit. Now, by date #2, if not date #1, we’re back at her place. The bad boy persona works well. Very well.

        Regardless, many women give sex with the expectation the relationship is “going somewhere.” You may be one of the exceptions as there is to every rule, but the majority of women want more Of course, even in post-feminist America, women having a serious relationship still means “I get your wallet (for her and her kids by another man) while I can still go have my bad boy or ex-husband on the side.” And Poindexter is just supposed to be happy about it, and accept that she’s “liberated” now. Of course, if marriage is in the cards, Poindy is not supposed to expect her to spend HER money on maintaining the household (because, remember that liberation thing?), because -frowny face – “life has been so hard on me and my kids because I’m female.”

        You think I’m full of it? I’m thinking of the acquaintance who just told me last week is single mom girlfriend of two years – a 44 year old mother of a 20 year old drug addicted ex-con son, the mom still lives with her own mother because she has nothing financially to offer – told him she’s afraid he “won’t meet her financial needs”, which is her dream to live in a beachfront house. He makes 4X what she does, he pays for EVERYTHING, and that’s the consideration she gives him. Not to mention he has kids, and doesn’t want to move to the beach, so he can be near them…but those aren’t her kids, so she doesn’t care (hmmm, like most single moms I’ve met who feel entitled at the expense of men) In addition, she mentioned to him that he “should put me (her) on his life insurance policy in case anything should happen to him.” BULL EFFIN SHIT (sounds like an episode of “Forensic Files” in the making.) When he told her “No”, she mentioned how she’d called her ex-husband for “closure” (divorced for years) thinking that last jealous nerve in my acquaintance, might get him to reconsider. He’s been a real Poindexter, and hopefully he’s coming to the realization that no good deed goes unpunished in dating. In his “niceness” she sees weakness, and a man to be manipulated for his money.

        While I’m sure women see some of the same crap in dating, these types of scenarios are rampant. Why invest time into finding that person to commit to any more while all those dating rules are so confusing? No reason. Sex is fun. And best when there are few, if any, strings. When the Sun rises, she can go back to taking care of her ex-husband’s kids (and boink him if she wants), and paying her own bills. And I can be unencumbered by the choices she made in her past life. Nice guy no more.

  2. Alex Cockell on August 25, 2014 at 8:23 am

    if it’s confusing for neurotypicals – think how mindbending it is for autism-spectrum blokes like myself, who have AT BEST a “phrasebook” level of knowledge of the NT social sphere…

    • Emma on August 25, 2014 at 1:07 pm

      Darth, it is clear you have no problem getting pussy. But you never address the human need for companionship, conversation and a connection (alliteration accidental, sorry). Which, I sense, you find here on this blog. I also sense that you could use a hug. Can I give you a hug?

      • DarthW on August 25, 2014 at 2:07 pm

        Lol. We do agree on the three “c’s”. What i don’t see in my dating world is very many women who do any better at attempting to meet a man’s needs in those areas. Instead, most -not all, but most- of the women I’ve dated, and many who have married and divorced my friends, want the three C’s with bad boys, then with a nice guy they get selfish with the three C’s and only want the “fourth C”: cash.

        I do disagree that I need a hug, though.

      • Michelle Seener on August 26, 2014 at 10:30 am

        Darth definitely needs a hug!

    • Emma on August 26, 2014 at 11:05 am

      That sounds challenging Alex (learned something new today: I’m a neurotypical).

  3. Emma on August 26, 2014 at 10:49 am

    OK ladies — who wants to join me in a group hug for Darth?

    Darth – can you feel the love? Can ya?

    • DarthW on August 26, 2014 at 11:06 am

      Just like women. They think they can love a bad boy and change him. LOL.

      • Emma on August 26, 2014 at 11:08 am

        haha, touche’ ! I’m going to change you, Darth. Just watch me.

  4. Jason on August 26, 2014 at 5:33 pm

    I enjoyed reading this. You have a refreshing perspective. I think it comes down to connection and communication. I’ve been accused of being “brutally honest”, but that usually saves some time and energy for both parties involved. As an entrepreneur, time and energy is my lifeblood, so I want people around me who respect my time in all phases of my life. I appreciate people who value the same in return.

    • Emma on August 27, 2014 at 9:17 pm

      Thanks Jason – agree 100% with everything you wrote.

  5. Michelle Seener on August 27, 2014 at 2:58 pm

    Sometimes bad boys are bad boys because they don’t get enough love. I’m not sure Darth needs to necessarily be changed. Maybe just softened a little.

    • Mike Whelton on October 11, 2018 at 9:14 am

      That’s a really dangerous myth. “Bad boys” are “bad boys” because they’re jerks, and more often than not, jerks are abusive. There’s often an underlying untreated mental illness, such as narcissistic personality disorder or bipolar disorder. The fantasy that women can somehow “tame” bad boys with their hearts and parts has landed a lot of women in graves, even more in the hospital, and even more in emotionally miserable relationships. Trying to cure someone’s inability to take other people into consideration with love is like trying to cure depression with motivational posters. Don’t fall for the fantasy.

  6. Marissa on August 27, 2014 at 3:56 pm

    Oh, Darth. I’ll be the lone person here who says I absolutely don’t want to hug you.

    I do, however, feel…uh…uh…I don’t know if sad is the right word. You just have so much anger towards relationships with woman. I have only met a few woman out of thousands that sound like the ones you experience. I do hope some day you can find someone who is a match for you. Though with the jaded way you are talking…it’s gonna just be the same ole same ole. But…I have some hope.

    Ya, dating now is crazy. It was nice going on dates and getting to know people.I’m in a committed relationship now. It’s been great. We just started talking about the “future”. I don’t know if I’ll ever marry again, but I know these things.

    1. Never co-mingling money again.
    2. See number one

    The end!

  7. Marissa on August 27, 2014 at 3:56 pm

    (and I don’t want to hug you simply because I’m one of those crazy single moms…you might take my head off)

    • DarthW on August 27, 2014 at 10:54 pm

      Marissa, you are wise to 1) never co-mingle your money again, and 2) follow your rule #1 again and again. If you never insist to the guy that he co-mingle his money with yours, he will be impressed.

      Honestly, in my nice guy days I was overtly generous to a fault….my fault. It was always an easy trait of mine that enables a woman who feels entitled. It was always a way I showed my concern and affection.

      Interestingly, even as a “bad guy” I’m the guy my former girlfriend could have given that $100,000 trust fund, left by her dead father, in cash to take to her bank and deposit. AND every penny would have gotten to her account at the bank. Her ex husband was the type who went through that $100,000 trust fund long before I met her, AND took money from her children’s piggy banks. And yet she still struggled between choosing him or me: Mr Nice Guy. I believe she chose to have his penis inside her when I ended the relationship….Her tears about him betrayed her. And on that day I learned my own two rules:

      1) Always be a bad boy.
      2) See rule #2

  8. HarryBosch on August 30, 2014 at 7:57 pm

    @DarthW – A serious suggestion…get a copy of Robert Greene’s “The 48 Laws of Power” and read law #4, which is “always say less than necessary.” Then re-read it.

    When you go to such lengths to make your case, you come across as though you have something to prove.

    • DarthW on August 30, 2014 at 10:40 pm

      Hey Harry worry about yourself.

    • Emma on September 2, 2014 at 10:30 am

      Per my favorite quote of allest time:

      “Being powerful is like being a lady. If you have to say you are, you’re not.” – Margaret Thatcher

  9. High Heels Backwards on September 2, 2014 at 10:26 am

    I think Emma posted about just this issue the other day, but she focused on women. In any case, DarthW is writing about his own experiences/perceptions, and the mileage of the rest of us may differ. :-)

  10. B on October 13, 2014 at 1:57 pm

    This is exactly why men should not date feminists.

  11. Bill Bixby on December 16, 2014 at 5:03 am

    Your post sums up why I generally avoid dating feminists. Hold the door open for one and I’m oppressing her. Don’t hold it for another and I hear, “Just because I’m a feminist doesn’t mean I don’t appreciate a little chivalry now and then.”

    Trying to figure out what they want, or more typically, helping them figure it for themselves, requires so much effort that the effort becomes very obvious and forced. It then very easily begins to look desperate. “Is this what you want? How about this? Or this?”

    Meanwhile, my feminist date is wringing her hands, deliberating as to whether her paying the bill will make her look desperate to attract me or show her strong financial independence. Or whether sleeping with me too soon will prove her sexual independence, or is she just bowing to every man’s desire to sleep with anything that moves? What are the greater political implications for each and every tiny gesture? The fate of gender relationships for years or decades hangs in the balance!!

    That’s the problem: you’re not dating a person but an ideology. Once I pick up on this, I excuse myself to use the restroom, find our waiter and tell him to hurry with the check.

    Ironically, I do best when I simply ignore any pretense of worrying I might offend her somehow by paying or not paying, displaying my irreverent sense of humor, or whatever. After all, you’re a feminist, right? Fine, supposedly you’re tough then. You’ll get over it if I hold the door open for you. If you can’t, that’s fine too. Don’t let it hit you in the ass on the way out.

    • Emma on December 16, 2014 at 3:19 pm

      Look — shit is stacked against you. Do what you feel is right/enjoyable/maculating and then fuck her — literally and figuratively.

      Am I right?

Leave a Comment