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

    You know, I find the negative comments to this post rather sad in the extreme. There is nothing wrong with two consenting adults who have their eyes open and who take complete responsibility for their own actions to have any sort of relationship they desire. If the situation was reversed, I’ll bet that nobody would think the guy was “desperate”…instead, they’d say, good job!

    Sexism is alive and well, alas. :(

    And besides, savvy 20 somethings know that savvy 40 somethings could have written The Sensuous Woman…and beyond. :)

    Data points, Barbara

  2. JM
    JM says:

    I’m a 33-year-old woman, and this post is HOT (not to mention intelligent and candid). I’ve never read this blog before, just got the URL from a friend, but seriously, Ms. Trunk is obviously a smart capable woman. She can @#$@$ whoever she wants, no? It’s up to her to decide how comfortable she is seeing this dude, helping him w/ a job, potentially running into him at work-related things, seeing him w/ other women. As for the question, “When women get power at work, do they use it the way men do?” I’d guess no, in that we use power differently outside of work too. I suspect that some men would not worry about it though, and they wouldn’t help their young lovers if they didn’t want to! (Though helping might consolidate their feelings of power.)

    You can also go through this post and check the verbs to see how power plays out:
    “I reward him by heading toward my house.” You’re in the position to reward – and it’s up to you how.

  3. dadshouse
    dadshouse says:

    You brought a stranger to your house for a one-night-stand (okay, you met him again, but you didn’t now that at the time) – I’m fine with that part. I’m a single dad, and hookups are part of a single parent’s sex life.

    But you did that with your kids there? Um… huh. Doesn’t sound like the smartest or safest choice to make. But maybe life is different in your neck of the woods.

  4. Leo Sigil
    Leo Sigil says:

    I don’t understand how negative comments coming from both men AND women add up to sexism. That’s ridiculous. Particularly when you stop to notice all the positive comments coming from men and women as well as some well-intentioned admonitions. It’s just people sharing opinions. That’s hardly sexism. This goes right back to what I said about babbling about gender inequality creating a greater divide. And I think it’s safe to say Ms. T posted this with the understanding and intention of creating a lively discussion.

    P-Trunk’s personal life notwithstanding, yeah, you can do pretty much anything you want as long as consequences and the lives and feelings of other people don’t factor in to your selfish little equation. You need to be careful what you condone and just how you go about doing it. I’m sure Barb’s bangin’ as a virtual coach, whatever the hell that means.

  5. Alice Bachini-Smith
    Alice Bachini-Smith says:


    There are a LOT of 25 year olds who want to go out with good-looking, successful older women who take care of their bodies (that’s you). I found that out when my first marriage was falling apart a few years back and felt a bit flattered to start with, before realising it’s normal, and it’s basically all about sex. Not just sex skills, which (you’re right) can be caught up easily- it’s about attitude. Younger men assume that attractive older women will be much more self-assured, take more initiative, and generally gain a deeper enjoyment from sex than the average college leaver girl- older women are in their sexual prime. Young men like that!

    Not saying this particular young man is trying to exploit you (would have to know him!), just that someone like you can probably expect a lot more of this!

  6. Fripper
    Fripper says:

    hehehe…this is gonna beat that – Hate Tim Ferriss blog and the Farmer blog post…good prospect really.

    Arousing fantasies of both mid-aged women and 20 something s all over..nice!

    Madison is the place to be I guess…I don’t have a childish Facebook account though. Its time you went lower…I mean age wise …how about 21 year old young bull …next?

    Haven’t you really observed all your popular posts are either when you hate a Man or …almost sleep and of course really do the whoopie…with a Man? there is a pattern…emerging!

    Next blog ideas,
    1. When you sleep with a 17 year old + college advice thrown in
    2. When your kids see you in your birthday suit along wiht another man …also in his buff + some sex-ed advice thrown in

    you got it all girl…keep going

  7. Danny
    Danny says:

    Short answer… They don’t but most of us men wish they would.

    Now for your story. Wow Penelope, have you thought of writing smut books?

  8. Curmudgeon
    Curmudgeon says:

    I think that you’re asking the wrong question, Penelope. You think that men who have power use it in predictable ways, because those are ways that you have observed and experienced. I’d like to offer the thought that the men in your career who have used power to, well, influence/help/take advantage of younger women are distinctly a minority, rather than a characteristic of all. It’s just that you’ve not personally experienced the ones that act otherwise. I’m not passing judgment on anyone here, but rather noting that your experiences probably aren’t representative of men in power in general.

  9. Jamie Varon
    Jamie Varon says:

    Oh, how the internet allows people to say the things they wouldn’t DARE say to you in person. Because, it’s not the truth.

    Your feelings and your fears about this situation are completely valid. I’m glad that I have had the pleasure to talk to you and understand, firsthand, your confidence. Because, these are genuine concerns, and really the fact that so many are threatened by your honesty means you’ve hit a nerve. And you’ve hit on something that some people are way too afraid to talk about.

    But, you already knew that. ;-)

  10. virginia
    virginia says:


    My perspective is that this sort of thing has gone on since the beginning of time, if you believe the bible, Adam and Eve were supposed to have had some sexual/gender influence/responsibility with each other. If you're worried about crossing a line, try bracketing within the context of would you do this for anyone who asked you as a mentor or on a professional level (not just a guy you are sleeping with)? For example, I listened to your radio show and Dennis in SF has recommended numerous people to you in a professional sense. Is he sleeping with them all? Maybe you should make sure your friend is someone you would support career wise whether or not you are dating him, then you don’t make yourself feel pathetic if he turns out not to be a keeper (personally or professionally).

    Also, some feedback on your show:

    It was good for a first show. The pace picked up as you got further into it, some interesting guests and clever banter. I felt you drew out too long your initial questions to the first guest and occasionally talked over the top of them. But once you settled in, I think it was a reflection of who you are and sounded authentic and nothing you said made me cringe too much. Except maybe alienating people from Madison. I understand you are relating your personal experience, but it is kind of like here in New Zealand, people are always dissing the US and saying how “you Americans do this or that”. I see it like the person is just sour grapes. If you aren’t happy or making it in Madison, its because you aren’t fitting in. If you don’t like the way things are going for you, get out. Certainly your reason for moving there (cost of living?) is because you thought there was a benefit. You can’t have everything, free babysitters and Broadway and the low cost of living too. So while the culture is not what you are used to, it’s your inability to adapt that's making you unhappy because it is what it is and was like that before you got there.

    Cheers from down under.

  11. Helen
    Helen says:

    Just got a chance to read this today. Ah, Penelope….To me your blog didn’t have so much to do with how men and women deal with power at work, but another illustration of how you confuse meeting/socializing with men with geting ahead with your career/business mingled with having sex too early in the meet/socialize scenario). I agree with Curmudgeon-“I’m not passing judgment on anyone here, but rather noting that your experiences probably aren’t representative of men in power in general.” I think you need more experiences of just meeting, perhaps dating men for the enjoyment factor of their company, nothing else. When you need the ‘male work-factor consult’, you’ll find it.

  12. Single Mom Seeking
    Single Mom Seeking says:

    As the “other” single mom blogger who got slammed alongside you yesterday by a certain single dad…. I’m here to read what you had to say. Thanks for the honesty, even when you know you’ll a hand-slapped for it.

    Would it be strange to say that I’m honored to have been in such good company over that particular post, and all the judgment that came with it?

  13. BusiGirl
    BusiGirl says:

    You’ve got to admit there is a certain rush in knowing that you’ve achieved a sense of “power” that was once relegated largely to the men who were helping you along the way. But that kind of power is handled differently by women because we think about its consequences, discuss it with our friends and colleagues, and generally fret over it for days and days (blog post as case in point).

    I achieved that same rush early on in my career when I was helping a man who was slightly older than I, but not as sucessful. It was a very powerful feeling that also gave me a personal thrill – €“ look how far I'd come! – but after the fling was flung and he benefited from a degree of success, the excitement waned, the relationship ended, and I was left with? A brief period of loss and a few of the raw feelings involved in a breakup, but mostly a sense of accomplishment and a great memories from a fun experience not every girl gets to have.

    Why not use your power for his gain? Just know what you’re getting into. But you probably already do since you’ve been processing it for days and days… :)

  14. Andrew
    Andrew says:


    Forgive me, but his behavior sounds somewhat suspicious, and if I were you, I would treat any involvement with this man with a great deal of caution.

    Don’t get me wrong, I am sure that you are very attractive to men, but it would appear to me from your description that this man may have been stalking you or otherwise following you with close attention prior to your first meeting.

    Also, from your description, it appears that he has requested (but not necessarily received) a fair number of professional favors from you.

    Obviously, having never met this man, I would not be in any position to judge, but his behavior would appear to be somewhat manipulative, and all of this seems a little suspicious to me, particularly given your age difference.

    If I were in your position, I would exercise a fair degree of caution with respect to your involvement with him.

  15. Eve
    Eve says:

    Ah, so there IS more to career development than just “being a nice person” and “keeping in touch with your network”?

    You should add “sleep with anyone who might be able to help you” to your list of rules.

  16. Brian
    Brian says:

    I’ve been the 25 year old (actually 23) with the 30+ woman before. Asking people for professional favors and introductions is sensitive enough without adding sex and a relationship to the mix. I could not imagine asking her to introduce me to her industry contacts. Even if she offered without my bringing it up, I think I would probably avoid it and seek another path. Getting business-specific introductions may seem like a good idea at the time, but it just puts the wrong skew on a relationship. If you happen to be out socially with no agenda and meet these people it may be okay though. My view is that relationships should be about fun and enjoying time together, and business should be kept separate. There is a lot of wisdom in the old adage of keeping professional and private apart. I’m not really that fond of even seeing someone in the same industry. Unfortunately from the older male angle, many use this to their advantage in order to get women in the first place… to great effect.

  17. spunk brophy
    spunk brophy says:

    Wow, I normally don’t read posts this long – I skip through them quickly (I have a bad case of ADD…) but your story about the 25 year old hooked me……by the end I had forgotten what the meat of the post was.

    I think it’s creepy when people sleep with poeple to get stuff, help, money or advancements. I probably would handle it just like you did – not want to take on the responsibility for getting him a job, etc. I’d keep that work life separate from the dating. Unless you’re married to him…..

    It’s a double standard – you see, men take great joy in “helping” their 25 year olds. It makes men feel strong, superior, masculine. Women don’t have a need to feel that way. Maybe that’s why you aren’t compelled to help him out like that. Because you’re a woman, you probably “give” in more maternal ways – like making him coffee in the morning and making sure he’s remembered his sweater before leaving, things like that.

    Regardless of how equal life is between men and women, we still have our differences and double standards. And often, the double standard is not of benefit to men.

  18. le
    le says:

    was smiling so much I forgot to addess the topic … from my own experience … when I had the POWER I used it like a man on men who deserved such treatment … but all in all it was being a woman and working to my womanly strengths that got me the furtherest and best results.

    Some days that meant empathy and understanding, other days it was short skirts and killer heels … often mixing the two worked wonders … mass appeal … and after all was said and done it really was just a big popularity contest. Cheers le

  19. Beth
    Beth says:

    Very interesting…

    I sincerely hope that women do not use their power like men in the workplace. I sincerely hope that women learn to meld personality with management style and career trajectory, and break the mold of the boring white male power-holder. I think that a lot of female trailblazers made themselves into men. And used their power like thier male counterparts. But I hope that the new crop of female leaders learns from their mistakes, because the men they patterned themselves after sold their own sales conforming.

    With the limited given facts, I also understand your trepidation with giving career help to this young man. Your knowledge of him professionally is limited. Nothing is sadder than the man who props up an incompetent female for reasons other than her career aptitude, especially when her female presence comes to represent other women. That is what people really mean by the negative statement “sleeping your way to the top.” So hopefully, this is one practice women with power will leave behind.

  20. Joanne Tombrakos
    Joanne Tombrakos says:

    I think this is a brilliant blog post! I admire your transparency and your dialogue with your initial discomfort as well as with your intrigue with this man.

    The double standard still exists. What is acceptable for men in the workplace is a topic of discussion when the woman is the older, more powerful one. But that is changing.

    I look forward to see what happens next !


  21. cara
    cara says:

    You had me when he pinned you….THEN WHAT?!?!

    No, women do not use power in the workplace the same way men do. Usually. Men want what they want and zero in on that target. And that target could be anything, not necessarily sexual.

    Women? We want to analyze the hell out of everything. Some do it faster than others but I think it is a universal quality.

  22. DirkJohanson
    DirkJohanson says:

    I take note of the assumptions by everyone that when a girl sleeps her way up to the top, it is the guys that enable this that have all the power.

    Uh – isn’t the girl using HER power to get what she wants?

    Meanwhile, of course, as Guyinism recognizes, its the young, hard-working regular guys that are on the outs.

  23. Accept loss
    Accept loss says:

    The plan may be to force me to stay in this house. “This way they can show up and poison you.” Like they were poisoned by mom?
    Like they have poisoned their children, who will in turn poison their own children.
    And the neighbor’s kids too, no doubt. Good thing it’s not an issue down south:::Her favor as a motherblood provides her protection from herself.
    This cycle will continue until one of them decides to say “No.” to temptation.
    This is the individual among them who will be saved from Damnation, the one who will break the cycle. Otherwise their parents will do it to them again when they are reincarnated.
    I think how they may have reincarnated grandma into Cris. I can’t imagine they disliked her that much.
    Of course it may be protection:::They like her so to save her from herself they isolate her, ensuring this potential hard-core preditor has no outlet for evil.
    Except his father. After all, he lived with her before she “died”.
    I think we see this repeated in the Situation::::The Gods protected those with favor from themselves.
    And savor poetic justice.
    Accept loss.

  24. Misha
    Misha says:

    Great post on a tricky issue. Seems like it’s up to the individuals to decide what’s right for themselves and their own consciences in a given situation. The moralistic idea that sex always has to be sacred is silly, and the ethical use of power is extremely complex.

    The time stamp left me wondering, though, where was the farmer when all this was going on? Making cupcake power-plays with random 25-year-olds while in the midst of a committed relationship makes it less acceptable, in my view. Still up to the individual, I suppose, but somehow ickier.

  25. Jonha
    Jonha says:

    Hi Penelope,

    I am very much impressed with the 25-year-old’s gutts and subtlety. I like it how at how you dealt with it. I know the things you may be doing sometimes may not be right, but for some weird reason, I love how you reason them out. You don’t necessarily reason it out, you were merely telling us. It amazes me how you talk about your personal life like it’s part of your life because after all, inspiring others in an odd way is your way of life.


  26. Bill
    Bill says:

    Penelope, First, I’m at work, doing research on Mentoring. We are thinking about starting a formal program. Second, OMG! Should I be reading the above at work! Thank you for a view on “mentoring” that I hadn’t expected. Also thank you for explaining how some of my lovers have been so irresistable! Bill

  27. Miriam
    Miriam says:

    I don’t think the guy was manipulating her for work-help. I just think he thought she was attractive and wanted to hook up with her. Nothin wrong with that. Btw, I find that younger men are much easier to get with than men my own age. Hotter too. They think about sex more and calculations less. I don’t generally take advantage of this dynamic, but I sure could if I wanted too. I discovered this when I got divorced. I was in my late thirties and the guys chasing me were in their early twenties. The same thing still held throughout my forties – and the guys were still in their twenties. I had a dating profile up and a very hot eighteen year old wrote me – I’m now in my early fifties. Yeah, I look good. Decent, at least. I don’t go after those young guys, though, because I don’t think there is any long-term potential there. They had zero interest in my ‘helping’ them with anything – I was not in any position to do so – just trying to survive post-divorce. So again – I just think that the young guy was interested in her, period.

  28. Mimi
    Mimi says:

    I don’t think the guy was manipulating her for work-help. I just think he thought she was attractive and wanted to hook up with her. Nothin wrong with that. Btw, I find that younger men are much easier to get with than men my own age. Hotter too. They think about sex more and calculations less. I don’t generally take advantage of this dynamic, but I sure could if I wanted too. I discovered this when I got divorced. I was in my late thirties and the guys chasing me were in their early twenties. The same thing still held throughout my forties – and the guys were still in their twenties. I had a dating profile up and a very hot eighteen year old wrote me – I’m now in my early fifties. Yeah, I look good. Decent, at least. I don’t go after those young guys, though, because I don’t think there is any long-term potential there. They had zero interest in my ‘helping’ them with anything – I was not in any position to do so – just trying to survive post-divorce. So again – I just think that the young guy was interested in her, period.

    • Mimi
      Mimi says:

      Sorry about the double-post – it didn’t look like it went through the first time, so I changed the info and tried again.

  29. Jacqueline
    Jacqueline says:

    How can women use power in the workplace like men do when they are paid 70 cents on the dollar that men are paid? Women don’t have the same power as men, therefore, they don’t use it in the same manner.

  30. Candice
    Candice says:

    Great post: raw and real.

    I like how you write about things that make people squirm. The world needs more of the truth! hushed topics that get publication.

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