When women get power at work, do they use it like men do?

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I told this guy who wrote to me that I do not remember ever actually meeting him, even though he says we had a great conversation.

He wrote back. He was relentless, so I asked him to tell me a bit about himself. He wrote, among other things, “I'm the guy you want to date.”

It was such a direct response. And I like direct. Plus, he was going to be in Madison. That never happens.

Two days before the date, I checked him out on Facebook.

Then I wrote him an email. “You are way too young. I can't go out with you.”

He wrote back, “You should know more than anyone else that online identities are deceiving. And anyway, I'm older than you think.”

That was a good response.

So we agreed to meet at a diner. For coffee. I walk in, and right away I know who he is: The guy with the backpack.

We sit down.

I lean across the table, and in a low voice I ask, “How old are you?”

He says, “I knew you'd ask that.” He says, “Twenty-five.”

I look around to see if people at the diner are staring at us.

He is surprisingly interesting. He's semi-pro in an odd sport, and he has a business plan to create a quirky application for the iPhone. We talk for an hour.

Outside he says, “I'd like to see you again.”

I think that's hilarious. I mean, I can't believe a 25-year-old wants to see me once, let alone again. And I can't imagine how things will unfold. So I say, “Okay.”

On the next date he knows the chef of the restaurant, so I think he does not totally have to pay for dinner, which is good, because he doesn't have the kind of job that could pay for this kind of dinner.

We talk about social media. He tells me about conferences he goes to in warm places with hipsters who live and breathe technology. Topics like iPhone applications for crowdsourcing get me excited. I am a sucker for someone who can teach me something.

After dinner he wants to go to a bar. We walk to one he can't find, and I am freezing and complaining and he slips his arm around my waist.

I think it was warmer with his arm there. Or maybe my body started sweating from the stress of walking through Madison with a twenty-five-year-old.

The bar is loud. I lean over, close to his cheek, and say, “I have to leave now. My ex-husband is with the kids and I told him he could leave at 10:30.”

The twenty-five-year-old looks at me.

I go on. “Maybe we need a plan or something. I mean, I need to either drive you back or drive you to my house.”

He says, “Let's go to your house.”

In the car I tell him it's crazy to take him to my house.

I look over at him. He looks back.

“Okay,” I say. “Okay. My house.”

In the car I imagine him at my house, and he will have to take a cab home, and it seems like a pain. And the potential for awkwardness is huge.

At a stop-sign on a dark road, I say, “I'm turning around and taking you back.”

He takes his seatbelt off, leans over and kisses me. It is a very good kiss, slow and soft, and a little bit wet. And it seems very hard to do that when the whole rest of the evening is riding on one kiss. I reward him by heading toward my house.

My Ex is at the house when we walk in. The guys I work with are the same age as the twenty-five-year-old, and they've been to my house late at night many times, so my Ex assumes I work with the twenty-five-year-old and he's chatty.

When the Ex leaves I take the twenty-five-year-old into the kitchen. I tell him, “It's my son's half-birthday tomorrow. He needs cupcakes for school. I have one more batch to make.” Then I start dripping gooey batter into superhero foils.

The twenty-five-year-old is patient. And anxious. I sit on the counter and watch him watch the cupcakes, and then when he's within reach, I scoop him over to me with my legs.

We cannot kiss too much because there's no extra batter if this batch burns. I am focused on cooking.

Then we go upstairs.

When he pins me against the wall, our age gap dissipates.

Fast-forward: I have seen him again. Though not a lot.

I've seen him enough to get flashbacks to when I dated guys a lot farther along in their career than I was. It was exciting. They knew a lot more about sex than I did, but you equalize on that pretty fast. And then, what's left in the inequality department is career stuff. And I could always figure out how to get stuff from them.

It was exciting to be the young girl who the older guys want to help, and date. At the same time. I was never sure how much I wanted either offering, but I knew that together, they were intoxicating. I want to see what that's like from the other side.

I am nervous with the twenty-five-year-old because of that. He asked me why I'm not following him on Twitter and I told him I forgot. But I didn't forget. I read his feed all the time. But I didn't want to look like a stalker, because so many times in my life, the older guys felt like stalkers to me.

The twenty-five-year-old asks for a lot of advice with work. He is, after all, working in my field. Almost everyone he has needed to get in touch with is someone I've had lunch with. I'm also very hesitant to ask friends to help a guy I'm having sex with. In the past, when I have seen executives do this with marketing girls (I have seen this a lot, actually) I have been embarrassed for them.

So I have not helped him that much, honestly. And in bed one morning I say, “How come you haven't asked me to get you a job?

He says, “The thought's occurred to me. I figured it would eventually come up.”

I don't say anything. I don't want to help him get a job. I want this to not be about all the stuff I could do for him. But all the older men I dated when I was his age were people who helped me with my career; they it did gracefully, and I was so thankful.

I started writing career advice because in my career I found myself constantly in situations that made the old workplace rules seem irrelevant. I realized the workplace had changed, and I wrote advice as I lived through it so the next wave of workers would have a relevant guide.

Today I have an amazing network of men and women who help me guide my career. But periodically I find my career lands me in a spot I have not been before. Right now I feel clumsy. Like the people who write long emails to me, thinking I have not heard their career problem before.

When I started writing career advice, the questions I answered were is job hopping bad? Is being lost bad? Today I find myself wondering: When women get power at work, do they use it like men do?

117 replies
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  1. Melissa
    Melissa says:

    Wow. That’s a really difficult, challenging part about being a female with a career, that NOBODY IS TALKING ABOUT. I am so thankful that you’re talking about it.

    You are INCREDIBLE at talking about the things that people SHOULD talk about, but don’t. Which is detrimental, because it makes those tough things even more difficult, challenging, and terrifying to deal with.

    Remember when you blogged that the hardest thing about parenting is that nobody is honest about how hard it is? That is the absolute, single most difficult thing about being a female with a big, powerful career. Nobody is being honest about how hard it is. Nobody is talking about the unique sets of challenges that it presents to females.

    Sure, everybody has career advice. There are a lot of people writing about career advice. Intuitively, I know it must be a crowded field, because there must be plenty of people who realize that because they’re so good at marketing, they can talk about how to build a great career instead of actually, you know, building a great career.

    Because building a great career is HARD. For anybody, and not any more or less so for a female. But for a female, it’s not always as neat, because you can’t do it in a vacuum. You can’t just draw a clear little line between work and life as easily as men can, because there are children and complex issues of gender and sexuality involved.

    But it’d be so much easier if people stopped pretending woman can just be men. We can be in the leagues of men, of course, nobody is questioning that anymore. But that still doesn’t mean we can turn ourselves into men and cease to feel and think like a woman.

    Even still, that admission alone wouldn’t be enough to keep me reading someone’s blog and coming back every day for more. You let me get to know you as a person, and that’s why I come back. Most people are scared to let other people see them as a person, because then they’re exposed as (gasp!) HUMAN. Human like the rest of us. And they realize that once they’ve revealed that they’re human to the internet, they can’t take it back.

    I admire you so much. It’s really not easy to be brazen and blaze the path for the rest of us. The reason it’s that’s scary is because we’re not static people. We’re all fluid and constantly evolving. Because we’re human.

    But it’s hard, lonely, and sad to be human if everybody is pretending to be a superhero.

  2. Fabulously Broke
    Fabulously Broke says:

    I don’t think women use power at work the same way as men. But it really depends on the field and their personality. Some women shy away, not knowing how to wield the power, and others get power hungry, trying to be a dominatrix bitch (yeah, I said it), and in the end, achieving nothing.

    The best is having a firm hand and being clear about deadlines & responsibilities but being flexible at the same time.

  3. Pat
    Pat says:

    He must be hot for a line like “I'm the guy you want to date” to work. Sounds like he subscribes to the “Double Your Dating” eBooks. Not that I ever have. I’ve just heard about it. I swear.

    Will future Harlequin romance novels feature experienced career women meeting younger athletes? Maybe they do now?

  4. andrea
    andrea says:

    Penelope, I love your blog, but this post kind of creeps me out. You have absolutely no problem admitting that you used your prior intimate relationships to boost your career, but now that you’re in a position to help out someone you’re sleeping with, you’re having qualms. Well, at least you’ve realized two wrongs don’t make a right.

    • heaven's sake
      heaven's sake says:

      Great, Penelope, so you slept your way up in your career. So all the other women who did NOT sleep with the guys that were helping you talk to people were edged out. Thanks a lot. And now you’re cavalierly writing about it as if it were nothing, or even expected. Well, in case this comes as a shock to you or to any young women who read your blog, most women do not behave this way, and it is morally wrong. It hurts you, the man, and other women (and men). Shame on you.

      • SuzyQ_826
        SuzyQ_826 says:

        Andrea and Heaven’s Sake,

        I really think that you’re rushing to judgement in your responses of “you used your prior intimate relationships to boost your career” and “you slept your way up in your career”. I’m not sure that you thoroughly considered Penelope’s motives or intentions.

        Penelope writes about men she dated as who happened to be in a position to help her achieve her career advancement goals and possibly introduce her to new opportunities. Nowhere in her post does it say or imply that she purposely sought out men who could further her career and deliberately initiated a sexual relationship with them. Now, that would be considered “sleeping your way to the top”.

        You admonish Penelope as if she wantonly traded sexual encounters with directors and CEOs for career advancement. Just because men she dated could or did help her career doesn’t mean that was her only motive, so why do you assume that?

        It’s not a crime to help someone you care about, whether it’s a friend, sibling, or significant other. And who would not want to help someone they were dating, especially if they were in a good position to do so?

  5. Mike
    Mike says:

    Nothing like brazen candor in the morning!

    P – When you’re looking for an ego boost before those big investor pitches just remember there are more than a few mid to late twenty somethings that would happily step into new-guys shoes. Like me.


  6. Rachel - I Hate HR
    Rachel - I Hate HR says:

    This guy sounds like bad news. If this guy wasn’t 25 and was 50 instead you would be running in the opposite direction. He sounds like a cheap manipulator. He doesn’t have to ask you to get him a job because he’s manipulating you into doing it.

    • Brad Fults
      Brad Fults says:

      How conspicuous is the line between “manipulating” and, all else being equal, pursuing a path that will benefit you? I’m not convinced that deviousness can be so quickly ascribed to someone in his position.

      I think it all hinges on honesty: unless one party is lying to achieve manipulation, it can’t really be called manipulation. If both parties are honest and aware of their motives, it’s just cooperation.

  7. Holly Hoffman
    Holly Hoffman says:

    Lending Melissa’s comment a giant HEAR, HEAR!

    I haven’t read any blogs by male executives about the ethics of helping the careers of the young girls they’re diddling. I pretty much assume they’re too busy worrying about their own careers and how they’ll get some more hot young ass.

    The issue is interesting. Do you use what power and influence you’ve come into to help this guy out? Would you be doing it if you weren’t sleeping together? At some level, you must wonder if he’s sleeping with you as a means to an end (which is probably what all the male execs assume and are OK with).

    The dilemma is different for women, I think. We’ll question whether the one has to do with the other, and men assume that it does.

    Is the sex the perk, or is the career help?

  8. Kevin Marshall
    Kevin Marshall says:

    Not sure why, but I find my self rubber-necking this post big time!

    Anyway – a couple of my personal opinions/questions:

    1. Are you hesitant to help the hacker because you feel it would cheapen your relationship or because you think he would cheapen your business persona (ie. you would be getting him into something you don’t think he’s really ready to step up to?)

    2. When you’re in a position of power, you have the freedom to do as much or as little as you want…but in the end, I think it’s more about the person in the weaker position…if/when it was you, would you have wanted the help? Would you have taken the help? How much would you have wanted handed to you because of the situation, and how much would you have wanted to earn or maybe better stated, how much would have wanted to be recognized for?

    3. Being in an intimate situation/relationship, you have an opportunity to learn and recognize many of the strengths and weaknesses of another person…encouraging the strengths (via contacts, jobs, or what have you) or shielding the weakness (via avoiding certain introductions or exposure to events/people) is only natural and seems like the most human thing to do (regardless of the gender of the person in the power position)…

    4. What flavor were the cupcakes?

    Anyway – thanks for sharing another great personal story (scattered with lots of nuggets for the brain to chew on)…

  9. fanf
    fanf says:

    Thanks for the share.
    This is a kind of interesting situation :)
    Hope you’ll find a way out that you’ll be feeling good with.
    Keeping it simple works I think. Most of the time. But that’s my own opinion.

  10. Barbara Ling, Virtual Coach
    Barbara Ling, Virtual Coach says:

    What a truly wonderful post! Your point:

    “But all the older men I dated when I was his age were people who helped me with my career; they did it gracefully, and I was so thankful.”

    Sums it up very well indeed. Back when I was in the corporate world, I had several friends who looked out for me (not dating, alas, but mentors all the same) …and I try to honor that and return that favor today by helping out the millenials who workout with me at the dojo. It’s called ‘passing on what you have learned’. Yoda certainly hit it square on the head.


  11. NYC Memories
    NYC Memories says:

    I don’t think women use power equally, at least I don’t. But, I don’t know if it’s purely an gender issue or gender + age. I think younger women in their 20’s really use power differently than men, but when I look at the older women in my company, they seem to utilize power sort of similarly as the older men.

    So maybe women change over time, and become like a man the longer they stay in business.

  12. XENCOR
    XENCOR says:

    I have half-a-mind to call you a selfish-whore…but atleast you are honest…and smart enough to tittilate the readership to more blog visits…only less than 25 comments so far….thats odd!!

  13. Stephanie
    Stephanie says:

    I was wondering what your kids think about you bringing home someone you just met on the internet and having sex while they are in the next room? Is that something that doesn’t bother you? You seem to introduce anyone you meet to your kids. This is something I am curious about as I am also a single parent and am the complete opposite. I feel I don’t want my kid to get attached to anyone unless I know the relationship is going somewhere.

    • Anna
      Anna says:

      What gave you the idea that Penelope’s kids are in the next room while she’s with the 25 year-old? They could be in a completely different area of the house. There’s no reason for Penelope to stop having an adult love life, just because she’s divorced, as long as she’s discreet about it with her young’uns.

      • Technologist
        Technologist says:

        If you actually think it’s about the location of the bedroom, you’re missing the point entirely. I suspect the commentor is more-so appalled at the lack of value that Penelope apparently views sex as having, hence she’s willing to “give it up” so easily for a quick endorphin rush. This isn’t advice, it’s a classic case of an emotionally damaged, ADHD person spewing miasma.

    • gregcnorca*AT*aim
      gregcnorca*AT*aim says:

      This particular blog probably wont satisfy a need for traditional values (I personally am taking no sides!).

    • Kandi
      Kandi says:

      You may not have as much power as she does. The more power, the greater the gender equality and responsibility sharing. The children’s father is actively in their lives (almost to the point of living with them), so I don’t think they’re phased. Plus, her being in a position of power usually means the kids don’t look down at her as if she’s JUST a mom who is there to cater to their every single need. They seem to have come to learn to rely on others as well as her and trust that their mother is a responsible human being. Because of the trust they have in their parents, they can handle the various types of contact they will have with people – short term, long term, personal, professional, etc. They’re not looking for a replacement daddy because they already have one. This is ideal. Very ideal. This is not to say that what you’re doing is wrong, but to show a perfect example of the freedom that can come of women being treated as human beings first, and how it doesn’t destroy kids lives *gasp* and enhances her own quality of life *double gasp*.

      • Stephanie
        Stephanie says:

        If I wasn’t so secure with my power I might be offended by that comment. ;) haha I think it’s great she is enjoying her life. She is open about a lot on her blog and was asking because I am always interested how different women handle that situation. My situation is also ideal. My ex lives 5 min away and is very involved in our daughter’s life. We attend her functions as a family, which includes his Wife and Step-Daughter. Am I protective of my Daughter? Yes I am. As a matter of fact yesterday I wanted to “Enhance my own quality of life” so she stayed with Dad and he took her to school in the morning.

    • Kandi
      Kandi says:

      Perhaps not sounding so judgmental next time might help (*gasp* sex. kids in house. *gasp*). And very glad to see you care about your quality of life as well.

  14. Kevin
    Kevin says:

    Interesting post. This sort of behaviour has been perpetuated by men for millennia. Now as demographics are shifting, more women will find themselves in this situation. More women are going to college and graduating and assuming positions of power. Enjoy the perks, because you will also get more heart attacks, cancer, and all the diseases (or their equivalents) that men get with “power”. I wouldn’t help this guy at the moment. It’s what he wants. True “power” isn’t about the wants and needs of the supplicant, it’s about your wants/needs. So Penelope, if helping out is what you want, then go for it. If not, relish the moment.

  15. cd
    cd says:

    p – it would occur to me that perhaps it’s not you (in this situation) that has the power. you may be “traditionally” experienced and successful than your mate; but (the way i read it) im not sure youre calling the shots…

    the fact that youve written this down the way you have (i think) suggests youve been played right into something.

    • Janice
      Janice says:

      I second cd in that your tone in this piece suggests you’re not sure you’re the one calling the shots… Also second whoever asked if you felt hesitant to help this guy out for ethical (?) reasons OR if you feel hesitant because you don’t think he’s worthy of staking your professional reputation on him? If the latter, ethics shmethics, he doesn’t deserve it, period.

    • Anca
      Anca says:

      And I read it as her being excited by him calling the shots (at least romantically). Given that she calls the shots everywhere else in her life, I have a feeling this role-reversal is something she craves.

  16. Evelyn
    Evelyn says:

    I work in an industry where the old boys club is still in power, but most of the up & coming or assistant level positions are women. I agree with NYC memories that women in their 20’s will probably use power differently than the men in power now, but won’t men in their 20’s also end up using power differently?
    I’m on the VP track, and my style is very different than my middle-aged-guy boss on so many things. But when I’ve got his job, I’m going to be asked to do the same thing he does — that more than anything will affect the way I handle my power.

    About sex & wielding your power, get over it. It’s nothing new; a little role reversal is good for you.

  17. Carol Saha
    Carol Saha says:

    Older woman, younger guy or older guy, younger woman. The whole thing hinges on intent and expectation. Like with any other relationship. Enjoy the relationship as long as you can and use your power to help him out. My two cents.

  18. Karen
    Karen says:

    An interesting story to reach an even more intriguing question. I’m not sure if he’s trying to use you just because he thought about asking you to help him with the job market. I have young students asking me to do the same for them everyday, granted it’s my job, but regardless it is on everyone’s mind and at least he’s being honest.

    I would tell him what I tell everyone who wants me to hand them a job on a silver platter… I can’t do that because of EOE and ethical reasons. But, what I can do is introduce you to people with whom you can then network and possibly lead you to a job opening or offering. Basically I leave it in their hands to impress professionals in their field; because how can I vouch for someone I’ve never worked with or known in a professional manner? Penelope, I would consider bringing him to a local professional networking event and/or a luncheon or meeting out with colleagues. This way it looks more professional or like someone who is job shadowing you. Which isn’t a bad idea since he’s in the same field as you.

    I’ve always been a subscriber to the independence/stand-on-your-own-two-feet philosophy. I was raised that way and it’s actually a masculine quality instilled in me by my father and mother. So, I don’t know if men and women in the workforce really would react that differently but I do think the difference of responses rests partially on one’s level of education. It’s been shown, through gender studies, that women with higher levels of education will report more masculine qualities and possibly score more androgynous or masculine rather than feminine on the scale.

    Who knows, the men you’re referring to in the blog may have just been worn down by their significant other or felt the need to take care of them because of an age gap.

    And, since we’re talking about age gaps I think it’s only fair to bring up the differences between generations. The Millennial Generation attests to something called a “sense of entitlement.” Some, not all, of this generation believe that mediocrity should be rewarded and the minimum effort and work is good enough to get them into high level paying jobs. This is yet another reason why some may believe a job should be handed to them, because their mom thinks their “great!”

    Do men and women behave differently with power? Yes, I think they do but I don’t think it’s just because of their gender-role. I think there are a number of other factors that play into decision making, like education, status, and generation differences.

    • gregcnorca*AT*aim
      gregcnorca*AT*aim says:

      to Karen: I predict he was thinking sex first (by a longshot), then about getting a job. Twenty five year olds have fairly straight-forward needs hierarchy. But I shouldn’t generalize.

  19. Tina
    Tina says:

    You are old enough where your personality is hard to change now, but you are too honest!!! This blog made your life wonderful, but it’s also going to cap your life until you get rid of it. You need another honesty outlet besides the WWW.

    You do know that if you weren’t semi-smoldering looking, you wouldn’t get to work that heated mind + physical chemistry you have with men, right?

    Stop sleeping around! I know, I know. It’s annoying when strangers tell you how to run your life and you want them to write you a 5 page proposal, so you can choose the best one or whatever.

    • gregcnorca*AT*aim
      gregcnorca*AT*aim says:

      “Semi-smoldering” (I’m laughing at such a phrase.) Words of a person on a fence!

    • Jean
      Jean says:

      Aren’t you smarter than to sleep with a guy you barely know? Seriously, where do you get the time to date/sleep with so many guys with your floundering start-up company, exercising everyday and raising children? It’s kind of hard to take you seriously when one week you’re crying to an investor about not being able to pay your employees and the next week you’re spending your nights hooking up with a guy almost half you age. What are your priorities?

      • Prettygeeky
        Prettygeeky says:

        Wow – apparently we are not past fratricidal morality that dictates that a woman should not have sex when & with whom she wishes… Though your math skills bear comment too…I cannot take a person seriously when they think that 25 is half Penelope’s age – argh!

      • Jean
        Jean says:

        I’m not crappy at math – I know that Penelope probably isn’t 50 (though who knows for sure). It’s called a hyperbole to make a point – this “relationship” clearly isn’t going anywhere – this 25 year old guy isn’t going to be a father to her children. I think that at a certain point in your life (like when you have children) you need to make the relationships in your life count for more than just sex. It isn’t a question of morality, it’s a matter of being responsible and respecting yourself and your family.

      • Jean
        Jean says:

        Prettygeeky – if we’re going to start questioning each others ability in basic skills (such as math), what exactly do you mean by fratricidal morality? Fratricide is the act of a person killing his or her brother. Am I supposed to take you less seriously now?

      • Peter
        Peter says:

        Jean, the kids already have a father. He seems to be doing a good job.

        What you are trying to do is impose your values and rules of conduct on Penelope, which is pretty close to what Merriam-Webster’s dictionary has to say about the word morality.

      • Jean
        Jean says:

        Yes, Peter I have values and yes, I am sharing them. I guess you are right that I should not judge, because Penelope is a person and sometimes I lose sight of that when reading a blog. Again, I would reiterate that it’s hard to take Penelope seriously when one week she’s crying over not being able to pay her employees and the next week she’s blogging about how she’s spending her nights sleeping with a guy she barely knows. Maybe I don’t value sex as much as you do, but I can’t respect someone who makes promises to people (i.e. employees) that they will get paid and can’t deliver but finds the time to get off.

      • Peter
        Peter says:

        It is not a question about how much you or I value sex Jean, the question is rather what Penelope does outside of her work hours and whether it is up to us to judge her.

        I personally believe that happy and balanced people perform better at work. I doubt that calling investors in the middle of the night is the right way to raise money to her company, which pretty much gives her three options for what to do with this time in the middle of the night: sleep; work on things that don’t require any direct communication; or have a personal life.

        If we accept the premise that happy and balanced people perform better the conclusion is clear: pick alternative one or three. In this case she chose the latter, and it’s her choice, whether we like it or not.

      • Jean
        Jean says:

        As far as I can tell, Penelope doesn’t have a normal 9 to 5 job anyway and it’s not crazy to work at all hours until you have funding to pay people who are counting on you for their livelihood. She wouldn’t be calling investors in the middle of the night, but she could be researching investors or writing emails or creating presentations or a million other things. If I couldn’t pay people that I had hired I wouldn’t have any social life until I fulfilled that commitment. That’s just me though. I would rather follow through with my commitments rather than satisfy my sexual needs. I couldn’t be happy or balanced if I didn’t pay people who relied on me.

        The hesitance that Penelope described in taking backpack boy back to her place was her conscience telling her it was a bad idea. If she wants to indulge in the love life she had in her twenties, that’s her prerogative, but that doesn’t make it questionable (she questioned it herself).

  20. PCD
    PCD says:

    Well, that’s one way to justify prostituting your way to the ‘top’. How many therapy sessions does it take to erase the memories of those men that traded career help for sex though?

  21. John Erik Metcalf
    John Erik Metcalf says:

    Great post. I’m always a fan of people who can say things like this. Who can be honest with the world about events and happenings that are kept hush-hush, but actually happen all the time.

    One point I wanted to make is to the people in the comments who are wrongly accusing you of “sleeping with him on the first date.”

    Do first dates even exist any more? Legitimate first dates, that is. I think the concept is made totally obsolete by the internet.

    The phrase “first date” used to denote that you had no prior knowledge or experience with that person. And of course, you would never sleep with someone in this type of situation because that would be reckless and possibly dangerous. It would show that you make weighty decisions without ample information. But that’s not what either of you did here.

    He’s had the chance to get to know you through your blog. Which chronicles your entire life, in a way so honest that other people can’t manage it or aren’t brave enough to attempt it.

    And you’ve had the chance to get to know him through Facebook and Twitter and all of the email and text and phone calls you likely had with him. He probably has a blog too. And even if he didn’t, you could Google him and then be perfectly able to piece together parts of his life and character.

    “First dates” will never mean the same thing.

    So, I have admiration for you both, for embracing the new standards of dating. Thanks for sharing it with us.

  22. DC
    DC says:

    I wonder, if in the case of power, do women really want to act like men did/do? Why would you copy the morality of those whom you don’t admire?

    @ John Erik Metcalf Your question, “Do first dates even exist any more? Legitimate first dates, that is. I think the concept is made totally obsolete by the internet.”
    –That’s so sad. I feel sorry for those who’ve never had a real first date. I’m not talking about blind dates, but true first dates…something lost? I hope not.

    • Holly Hoffman
      Holly Hoffman says:

      I’ll verify @ John Erik Metcalf – First dates don’t exist anymore, not in the traditional sense. There’s email, there’s text, there’s Facebook. In my generation’s logic, why would you want to go into without knowing enough to know you’d like to date this person?

      And it’s not sad. It’s reality. Just think of all the horrible first dates we’ve been spared by finding out he’s actually 44 on his Facebook page.

    • John Erik Metcalf
      John Erik Metcalf says:

      @DC – Don’t be sad. Things are not worse, just different.

      Think of it this way instead. Be happy that generation to come will be able to start interactions at a higher, deeper, more meaningful level.

      • Ian Selvarajah
        Ian Selvarajah says:

        “Be happy that generation to come will be able to start interactions at a higher, deeper, more meaningful level.”

        I would argue that the exact opposite is happening. Someone’s blog is still a *window* into their life, not the full picture. I hope someone doesn’t actually think they know me based on what they read on my blog.

  23. Grace
    Grace says:

    I think women do use their power the way that men do.

    The only reason Penelope is unsure about how to proceed is because she remembers how she felt and thought when she was the younger one in the scenario.

    If she hadn’t experienced it from the “trainee’s” perspective, I think she would probably pull all her strings to help this fellow, as she would for anyone she had developed a caring relationship with.

  24. Randy Zeitman
    Randy Zeitman says:

    I maintain my theory that one way women maintain control by choosing the circumstances of which they allow themselves to be seduced.

  25. Brenda
    Brenda says:

    P: I can’t help but think Brad Pitt in Thelma and Louise. Do it on your own terms!

    I believe in paying it forward; those who helped me are being re-paid by me in the currency of those who (whom?) I am helping now.

    So, if you truly believe he honestly is worth the currency that you have gathered from those who helped you, spend it. Otherwise, keep it in the bank for someone else. Only you will know the answer (and I sense from your post that you already do…)

  26. DC
    DC says:

    @Holly and John Erik

    I don’t know, you learn a lot from first dates–about yourself, about others. There’s that sense of anticipation and, yes, dread, that’s exciting. I’m mean you’ve talked to them. You’ve seen them in class, the diner, or in the office building. It’s chemistry, it’s attraction, the adventure, the racing heart, it’s the things that aren’t said. There’s something about this person that makes you want to go out with them. It’s taking a chance.

    So what if it’s a bad date. Really, you’re not only learning about life, but you’re collecting great stories, too!

    I’m not sure I agree that nowadays one would start interactions at a deeper level either. It all depends.
    Yes, there’s email, there’s text, there’s Facebook…all good, but not the same. Okay, it’s a generational thing, but I still have affection this rite of passage.

    Hopefully, John Erik, you’re right. It’s not better or worse, just different.

    Nice chatting with you both.

  27. sneaky
    sneaky says:

    This was a big share. Maybe now its time to show some performance pics from the vollyball career?

  28. Amber Warren
    Amber Warren says:

    When women get power do they use it like men? No. Those men who “helped” you into your career probably never stressed and worried whether what they were doing was wrong or immoral. They just did it. You’re pondering it, worrying about it and blogging about it. I think women, on average, are more emotional, sensitive and interpersonal than men. My opinion? If you really like him, don’t help him. At least, until you two are really serious and committed. If you don’t think it will go anywhere and don’t care, then help him. But just know that if you do that right away, your relationship will be over as soon as neither of you have any use for the other.

  29. HL
    HL says:

    Do you need a proofreader for your posts? Because you left out a word, ” they it gracefully, and I was so thankful.”

  30. Ask a Manager
    Ask a Manager says:

    To the handful of commenters who think there’s any sort of prostituting going on: Oh, come on. People do favors for their friends, whether they happen to be sleeping with those friends or not. There’s nothing sordid there.

  31. Irina
    Irina says:

    Just for you, Penelope, I’m daring to participate in the discussion :-).

    I’m happy that you are breaking stereotypes and sleeping/going out in public with that guy. Someone has to do it. And you are very brave for putting it out here on your blog.

    The whole idea of helping out a person you are sleeping with career-wise is fascinating. Somehow our society has attached a negative connotation to it. Helping out a friend career-wise is not at all a problem and very welcomed. What is it about sex that changes everything so drastically?

    Is it because the pleasure is so primal that it is shameful to even think that it is being traded for something? Why is it so bad to “trade” sex for other things? How is the gain in career different from a gain in happiness or some form of material gain? Or is it the age difference? Put another way, if a 35-year-old guy takes a 22-year-old girl out to dinner and pays for her and then they have sex, it is totally socially accepted and normal and there is no shame.

    • Andrea
      Andrea says:

      Irina, here’s a question in response to your question, “Why is it so bad to ‘trade’ sex for other things?” — in this case, specifically, for career assistance.

      My question is: was it foolish of me to be married by 25 because it actually handicapped my career? Are we encouraging young women to sleep their way to the top now (again)? I thought we were supposed to be moving past that paradigm. Or is it just such a dog-eat-dog world that we’re supposed to applaud success no matter how it’s achieved?

      • Evelyn
        Evelyn says:

        sometimes I wonder the same thing. Being married at 25 certainly hasn’t hurt my career, but it’s a nagging thought.

  32. Lance
    Lance says:

    Holy cow, this is smokin’ hot. This is the best post I’ve read all week. I don’t know how old you are, but the age gap only means something socially (ie externally) and I’m sure you are handling that.

    People transact sex for whatever every second of every day. It’s the way the world works. Don’t fight it. Bring value to people’s lives, always.

    Also, I kind of wish I was this dude.

  33. Steve Errey - The Confidence Guy
    Steve Errey - The Confidence Guy says:

    P – if someone sent you this post in an email, and asked you what you’d do, what would you say?

    It’s funny, I’ve just written a post about how sexy confidence is, and here’s a prime example (I might have to rewrite the article to link to this now).

    You’re a confident woman and the 25 yr old certainly seems to be confident. My guess is that he has a clear motivation for getting in touch with you in the first place and for keeping you interested, and I suspect you know that. I’ll leave to Lance to say whether he’s using any pick up strategies.

    What’s your role here? Mentor? Lover? Friend? Network hub? Baker? Same goes for him, what role is he playing in all this? Is he looking for forge a romantic or sexual relationship with you, or is he looking to climb the ladder in his field by climbing you?

    While I think there might be some confusion about roles here, I also think you should simplify things by sweeping aside all of those roles and just do what you do best.

    Being P.

    • Lance
      Lance says:

      Steve, that was the first thing I thought of upon reading this, the guy has some PU knowledge. I don’t think it matters though, because he seems genuine and obviously he’s bringing value to her life, so it doesn’t really matter how he attracted her, just that they’re attracted to each other and it’s real.

  34. Kelly O
    Kelly O says:

    I can’t help but come back to the point about the people you were involved with who helped you in your career, and the expectation that eventually this guy would ask for help too.

    Maybe it’s differences in individuals, but I can’t think of an instance where sex and work would come together at all. Talk has gone on in our house lately about me working with my husband, but that’s the only time in my entire existence the possibility would exist that I would sleep with someone I work with.

    I don’t think this has been addressed yet, but has this given you any additional thought into the men you’ve been involved with in the past, and how they might have felt about a PYT sleeping with them and then asking for something? I know the conventional thought might be the men weren’t thinking of that, but isn’t that just as broad a generalization as thinking it’s only women who consider those things?

    And I know it’s anti-empowered female to be concerned about bringing home a 25 year old on a first date to see your kids and do whatever, but come on… there is a huge difference between someone you like and who you think you might have a relationship with, and someone you just want to have sex with. I see what those same things do to my stepdaughter when her mom brings whoever she met out home, and it’s not a happy thing for the kiddo (whether empowered female mom wants to admit it or not.)

    I realize I may be in the minority, I just think the whole situation is messed up, and a really good reason to not mix “business and pleasure” as the saying goes.

  35. avant garde designer
    avant garde designer says:

    True, sex has been used as a power tool as long as there’s been sex. Still sad, though, when it’s used that way. It cheapens both the career accomplishments and the idea of true, loving sex.

    I’ve keep the two separate and feel a sense of pride knowing I’ve achieved both on their own merit.

  36. Dale
    Dale says:

    Woman are you crazy?
    I know you must have checked him out carefully before meeting him, but this is exceptional even for you. But then every other woman that I know well has been in this situation, and it was a learning experience for them too. I guess it’s part of life – think The Graduate.

    Help the kid, pat him on the head, and send him along on his way. That’s what will happen in some form anyway, so the best thing is to know it and to plan it in advance. Plus, aside from the sex, you could be a really good mentor to him, and he seems to need that from what you’ve written.

    Be kind to the boy.

    Most women that I’ve met do not use their power like men. Men are cruder in their use of power, and it is not always relationship based. There are more egos involved, a more ridgidly defined social structure, and it usually involves more men (boy’s club). Powerful women I know usually have a more even distribution of “followers and while there is a definite queen bee, there is more social democracy.

  37. Leo Sigil
    Leo Sigil says:

    I'm all for gender equality in whatever aspect of social, work or home life, and I think women should have fair access to what has largely been the boys' playground, but it seems to me that there is this implicit belief that in order to "catch up" women should be able to do what men do without facing the consequences men face. That hardly says equality to me. Lest I wander too far from course, my main point is this: It seems to me that people are skirting the most obvious issue – €“ credibility.

    Admittedly, I've only skimmed the comments, but in all the you-go-girls and for-shame-for-shames no one has mentioned the very tangible consequences Penelope could face as a "careerist." Granted, the lion's share of the latter half of her career is built on "revolutionary" advice (the quotes are in no way meant to be cynical or sarcastic, only to signify that I use the term loosely), but for all the changes occurring in the professional world and the general increase in moral relativism, I don't think the nature of integrity has changed. Anytime someone catches a break for showin' a little skin it reflects poorly on both benefactor and beneficiary alike. How common is the phrase, "slept her way to the top?" Of course, we're not talking about a woman feeling her way up the corporate ladder, we're talking about a guy. The difference being in the way the beneficiary is perceived: women who "sleep" their way to the top, however accurate or valid the accusation, are generally perceived as amoral whores. Women who allow men to sleep their way to the top more often than not come across as having been manipulated, not so much nurturing Madonnas as tools used for expediency. At least that's the general impression I get. Isn't one of the major points of feminism in any incarnation to do away with this kind of objectification?

    Some of you give Slick Mr. Backpack too much credit. One of the previous comments said it without saying it all: he's clearly confident. Confidence is best when tempered with humility. I don't think his confidence comes packaged this way. Maybe I haven't read it carefully enough, but this is what I see: P's a knockout for sure. And in a powerful position. And Backpack's a 25 year old male – €“ the age of opportunity. I slept with women twice my age when I was younger, and in retrospect I have to admit that it was all about conquering the mountain. I didn't necessarily realize it at the time, but I do now.

    I think P-Trunk touches on this concern briefly, but fails to ride the train all the way to the station. And since 30,000+ readers now know that backpack could potentially get a job through all his hard work in the bedroom, it probably wouldn’t be long before his potential coworkers figured it out themselves.

    I also think it's worth considering that rambling incessantly about gender inequality perpetuates gender inequality (Which is not to say that I don't think inequalities should be exposed, for those of you turning your ignitions). I just think it's good to bear in mind that language creates reality and language affects perception.

  38. Prettygeeky
    Prettygeeky says:

    I love the fact that you are so completely straight-forward & honest! One thought though…why do women still find the need to compare themselves to men? We now play in the same arena – but we can revel in our own special ways of performing. I love playing with men while maintaining my unique female qualities & perspectives.

  39. ioana
    ioana says:

    “I'm the guy you want to date."

    Yawzers. It’s obviously a game for him. Don’t waste too much emotional energy on this guy, just have fun and send him on his merry way. Help him/don’t help him – that depends if he’s actually capable. Can he sell more than used cars?

    I don’t believe in “the rules” or anything, my husband of 14 years started as a one-night-stand with a stranger, but my alarm goes off about the backpacker.

    • Anonymous
      Anonymous says:

      “To the guy I want to date: I'm wet. Back now from a walk downtown. Raindrops on my nose, squishing when I'm kissing, someone who is not you…”
      11:34 AM Dec 28th, 2008 from Twitter.

      That was hot, it got me. Penelope can’t include the whole story ;)

  40. David Coveney
    David Coveney says:

    I’m going to go whizzing riiiiight past the key points of the article and ask:

    Hang on, you celebrate half-birthdays over in America?

    As if there aren’t enough things to think about in a child’s life… blimey.

  41. Dale
    Dale says:

    @ Jean
    This stuff isn’t (couldn’t be) presented in strict chronological order of occurence. At least I don’t think it could.
    I think that some of what is posted is based on occurences in the past.

  42. sophie
    sophie says:

    No, we don’t normally celebrate half-birthdays in America. Except when you’re sleeping with a guy you’ve just met and you feel guilty about the kids. Then you over-indulge them, thinking it will make it all better.

    Penelope, hopefully this posting is fiction and you’re not really that desperate.

  43. Susan Su
    Susan Su says:

    Hi Penelope,

    I love this story, because I find it exciting and unreal.

    I’m a 25 year old woman, and get hit on in subtle (and not so subtle) ways at the all-male tech company where I work.

    I sense that I have a weird sort of power at my company – because I’m young, pretty, respectably educated, and smart. I also get the feeling that I’ve survived three rounds of layoffs – instead being ‘re-allocated’ to new, more powerful roles’ because of the strange and confusing power (or sex appeal?) that I have.

    Though it’s not PC, I try to leverage this as much as possible–anyone in today’s workplace who doesn’t, may be missing out on some prime opportunities.

  44. Irina
    Irina says:

    So I thought about your comment about executives sleeping with marketing girls and advancing their careers because of it and I would actually consider it sketchy. But only if the marketing girls were sleeping with them solely for that purpose.

    On the other hand, if the marketing girls were seduced by executives and were sleeping with them because they were attracted to them and had feelings for them, then the career advancement was just a “perk.” Then it is not so sketchy and actually seems to be pretty common.

    What is most important is that both sides have a sober understanding of what is going on and what the other side expects.

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