I met D at a party. I was there with Ryan Paugh and a few bloggers from the Brazen Careerist network, and because it was SXSW and it was all parties all the time, I was pretty partied out. But the party was for Kirtsy, and I love the women who run Kirtsy, so I went.

Also, Holly Hoffman wanted to meet Guy Kawasaki. And really, it’s not like I’m his best friend, but because I know him, I could say to Holly, “Oh, I’ll introduce you.” And I did that. And Holly was thank-you-thank-you, even though Guy is so nice that you can just walk up to him and introduce yourself and he’ll be nice. To everyone.

And I’m standing there with a bunch of 25 year olds, because I’m always hanging out with 25 year olds because that’s basically my job—I work with them and my business is for them. But I was not with THE 25 year old because the night before, I woke up to him peeing on the carpet in my hotel room.

When I asked what he was doing, he said, “Oh, sorry” and then he went back to bed. So I woke him up. And yelled at him.

He said he was drunk. He went back to sleep. I woke him up. I said, “I told you you had to go down on me and you didn’t. You asked a woman out after she wrote a whole blog post about oral sex and you don’t even do oral sex.

I’m pissed.”

He says, “I was too tired.”

“Too tired for ten times? We’ve had sex ten times.”

The night deteriorated and I told him to leave the next morning, by 8am.

He says, “Can you wake me at 7:30?”

And I say, “No, I’m not your mother.”

So at the party, that night, I was surrounded by 25 year olds, but not that 25 year old, and you can imagine that I was really happy when someone my own age came up to me.

But I really couldn’t tell why he was coming up to me. I have said before that I think I have Asperger Syndrome, and I think it’s full blown when it comes to dating. So I have to be direct. So when this guy who is clearly in my age bracket comes up to me and says, “Hi, I like your blog,” I ask, “Are you trying to date me?”

I know this is not normal. But I had been to a million parties and I had had a glass of wine, and I just wanted to sort people quickly.

He thought for a minute and then he said, “Yes.”

Great, right? He showed me that he can cope with my weirdness and still come out okay. So we hung out talked for a while, and then I realized my phone was dead. And the night was early and I needed to text people and so I wanted to go back to my hotel room to get my charger.

The guy said he’d walk there with me.

I tell Ryan Paugh because I think maybe I’m missing something.

Ryan says, “He thinks you’re having sex with him.”


“Yeah. You can’t take a guy to your hotel room and not have sex.”

“Oh. Wait. But I told him I need my charger.”


“Okay. Okay.”

So I tell the guy, “No.” Then I walk him over to his friends, who are at the same party, and I tell them our date is over: “I’m getting my charger and he can’t come with me because I don’t want to have sex with him.”

His friends laugh.

I think this is a good sign.

So the next night we have a date. It is very low pressure because he is from a state that is far away and does not have a direct flight from Madison. And he is not a gazillionaire, so he is not going to buy a house for us to share in Chicago when we meet at O’Hare. So: No future.

I tell him, “Be careful of that wet spot on the floor.” And then we have a one-night stand. At least I think it is going to be a one-night stand. But then in bed, I can tell that he’s not thinking one-night stand because he does sweet things that guys never do to me, like stroke my hair. I do that with my kids.

And then things deteriorate quickly. Well, for three weeks, things are good. I like him and I call him. And I see him again. Then things get bad because he twitters about me. And I think, I do not want the world to know I’m dating him because maybe I don’t want to be dating him.

And he tells me I’m out of my mind that I’m worried about who is twittering about me. He says something, which I will summarize as: Get a life.

So I am not with him. Because you can’t be with someone who thinks you’re out of your mind. And I’m not with the 25 year old, who, by the way, is also twittering about me, in an odd sort of way.

So I’m thinking the lesson here is that if work and sex are mixing then it’s a sign the dating isn’t working. But really, there must be a ton of people who think sex and work overlap because, look, my blog has 33,000 subscribers.

So maybe the lesson is I shouldn’t date people I meet through my blog. But then I think, who have I met not through my blog in the last two years? And maybe the answer is no one.

119 replies
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  1. virginia
    virginia says:

    Dear Penelope,

    I hope your blog is theraputic for you, and I appreciate your honesty. You may be doing a lot of people a favor by letting them see the reality of dating through your experiences. I think one thing thats happenning here is you are reinforcing the age old truth, don’t sleep with people unless you know them really well and are in a committed relationship with them.

    I know this sounds like something your mother would say and I learned the same way you did, by trial and error (I had no mother to teach me).

    Why risk your health, dignity, spirit and professional reputation by allowing some one to use your body as a rubber doll an pee on your carpet? You wouldn’t know they were going to behave like this unless you spent time getting to know them. Even after getting into a committed relationship, you are still at risk (ie Spitzer, McGreevy, Huffington and all the others who drop the bomb on their spouse). Why not narrow down the odds of getting involved with someone inappropriate and spend the time vetting them and learning about who they really are?

    Think of your own daughter and what you want for her then apply that to yourself.

    I think you are an interesting, smart person who has a lot to offer in a love relationship. Why squander it on every guy that crosses your path? Your high risk behaviour is not healthy for you personally or professionally.

    Love yourself and don’t give in to your lonliness and neediness. Get a grip and abstain from letting people ‘do their business’ on you then pee on your carpet.



  2. Justin
    Justin says:

    Honestly, I would say that the way you write has forced me to become oddly attracted to you, and I have no problem saying that because that is clearly the reason why you’re choosing to write about this stuff. A woman talking about one-night stands, just so happens to be, something probably every single guy in the world has fantasized about in one way at least a million times in their lifetime.

    I always find it funny when women are almost wholly unaware of how much power they really possess; it’s so clear why men had to suppress minorities throughout the ages to keep our power levels high. We’re all completely powerless against our penises. Mostly. Not at all the time. But most of the time.

    So yeah, I would totally ask you out. You ask for it. Sorry, but it’s true. ;)


    P.S. I do like reading about how you’re a savvy career woman and all, but the mix of the personal stuff in with the career stuff is really what I enjoy reading about. And I’m not a weirdo.

    • Lynne
      Lynne says:


      You said: “I always find it funny when women are almost wholly unaware of how much power they really possess; it’s so clear why men had to suppress minorities throughout the ages to keep our power levels high.”

      Don’t you mean “it’s so clear why white/European men had to suppress minorities”?

      • Jim C.
        Jim C. says:

        Why white/European men?
        Did you ever look at how the Chinese treated the “barbarians of the four winds” (Miao, Manchu, Mongols, Tibetans, Taiwanese, etc.) in the old days? How about the way the Tutsis treated the Hutus? Or the way Muslims treated (and still treat) the “Koufar” minorities in Muslim-majority countries? Did you know the Arab word for “Negro” (abd’) is the same as their word for “slave”?
        It’s very politically correct to blame white males for everything, but it’s a lie.

  3. Miss Joyful
    Miss Joyful says:

    Dear P.,

    I agree with many of the comments here. Your blog, which I subscribed to for professional advice, seems to have become a forum for you to vent about your personal life, and not in a constructive or informative way. I really do not think details about your 25-year-old boy-toy peeing in the hotel room while drunk, or turning down an opportunity to fulfill your oral sex needs, has any relevance to the issue of work intersecting with dating that you are pretending to address.

    Also, claiming that you have a medical syndrome to “explain” your issues of social awkwardness is an insult to people who actually have Asperger's and the people who love them. NOT very professional, Miss P.

    You are clearly suffering emotionally and professionally from your divorce, which, granted, is an extremely difficult life event.

    Please get some professional therapy and stop displaying the “train wreck” on your blog. Please do also continue to write honestly about issues, with less tawdry details and more common sense.

  4. Sari
    Sari says:

    I hate comments that start with the phrase, ‘as a single mother…’ but in this case, it is appropriate for me to express that phrase, because I get it.

    When you’re a single mother, working professional and blogger, and you’re trying to hold it all together AND find someone who understands you on the level that you want them to – be it sexually, intellectually, emotionally, or all three – sometimes blogging about the experience is the best thing to do. I commend you on your ability to be shamelessly candid, and for standing up for yourself after you have done so.

    The people who worry about you have never been in your shoes.

    • Lee
      Lee says:

      I’ve been in her shoes, so please don’t assert that since we are of the same ilk that I would have the need to sleep with 2 men withing a time period of 72 hours to keep my life together.

      I hardly consider a one night stand to be the standard for finding someone who understands me on all the levels you indicated. Men and women who engage in that kind of behavior are not looking for a deep relationship – they’re using it for instant gratification and in this case, material for the next blog roll.

      PT would you not be embarrassed if your parents or children read your soft porno? Imagine how they would feel knowing that you don’t care about protecting them from the consequences of your public porno.

      Oh, and I find it very hard to believe that you had sex with the guy ten times in one night when he was so drunk he pissed on the carpet. Alcohol and erections aren’t exactly good bed fellows. I doubt he could even get it up once. That’s probably why you were so demanding about him going down on you.

      I think you exaggerated or possibly made the whole thing up to increase your traffic and bask in the praise of your shallow, pathetic minions for the validation you so desperately crave.

  5. John Demp
    John Demp says:

    Wow, I read these posts all about sex and sure they are interesting and I enjoy reading them…like a romance novel. Is this stuff real or do you make it up? If it’s real, wow you are one slutty mom.

  6. fanf
    fanf says:

    Wow… You’re quite amazing :) I mean, all this seems such a mess sometimes :D

    Well, not dating someone only because you’ve met by the blog is quite a strange debate… There is shit and gold everywhere. And someone reading your posts, if you’re true there, should at least know you a bit. Which can be a good beginning.

    Dating and work(place), this is another stuff… This can lead to some shitty situations. And you’ll probably have to deal with the stuff each day, quite face to face… But this can be great too. Depends really on how you and your date can taste the present, be responsible, drive your own life… A quite huge risk if you live for your job in fact :|

    I wish you luck and strength in your mess ! Enjoy :D

    some PS:
    – Peeing on the carpet ? oO
    – If ten times is in the same night, maybe peeing on the carpet is not the important point.(joke)
    But ok, tongue play is still missing..

  7. Gerty
    Gerty says:

    For those that may be unaware, one of Penelope’s sons has Asperger’s, I think she would probably know more about the condition and its symptoms than most people.

  8. rebecca
    rebecca says:

    Sorry P. It was a cringe. Pure and simple. And not in a “you made me think deep thoughts” kind of way. More of a “ick how pathetic” kind of way. Love your blog and read it for years. I really think about this from a mother’s point of view. What does a mother of 2 of any business behaving in such a way as to endanger her own mental health and thus the ability of her to take care of her kids. Get off the train till you kids grow up. You are just not single anymore; you are a mother. People need and depend upon you.

  9. Mr. Chow
    Mr. Chow says:

    I love your confidence in posting this experience. I, myself, am very discreet about my office/work dating experiences as I commit to denials after denials when co-workers and friends asked about so and so….

    This is the first of many blogs that I will read at your site. I’m a blogger myself and will refer to your posts in the future.

  10. CAK
    CAK says:

    Penelope, what would happen if you became maddeningly aloof and hard-to-get? Would your appeal not appreciate?

    What would happen if you left the truly intimate moments, like touching one another’s hair, between you and your kids? And don’t expect those things from strangers–by their very definition, strangers are incapable of honest intimacy.

    I’m just saying: shuffle the deck and try some new, and perhaps opposite strategies, to make yourself satisfied. Not because you “should,” but because finding the balance between work and sex (or relationship)is a trial and error thing, and you are perfectly willing to do trial and error in the hopes of stumbling upon more insights . . .


  11. jafo
    jafo says:

    A compilation of my favorite lines from both the article and the comments:

    “So when this guy who is clearly in my age bracket comes up to me and says, “Hi, I like your blog,” I ask, “Are you trying to date me?”” – That’s not Asperger’s. That’s something completely different. And honestly, a lot more scary.

    “Then things get bad because he twitters about me. And I think, I do not want the world to know I'm dating him because maybe I don't want to be dating him.” – `Immediately after making this statement, Royal realized it was true.’

    “But really, there must be a ton of people who think sex and work overlap because, look, my blog has 33,000 subscribers.” – I don’t.. Uhh.. Wait, wat? That could have worked perfectly, without the “33,000” bit, no?

    “I’m a 50year old Jewish man that has been married and divorced (no kids), and I love hyper nuts intelligent gals like you.” – Is it just me, or does this sound like he’s a 50 year old man who enjoys women in spiky heels who grinds them into his nuts?

    “I am concerned that maybe there is something self-destructive in all this. I’m not telling you what you do.” – That’s awesome, how you tell her what she does, then follow it up with, `I’m not telling you what you do.’.

    “I have ground out my career are a product strategist.” – I SWEAR to god, what I said above must’ve been subconsciously taken from this.

    “I wish I could find one like you out here – we could be crazy with each other, and that nervous, trembling energy and creativity would be the boot in the ass I need to revive” – Ohhhhhh. Christ. Really. This just gets worse and worse.

    “Why shouldn’t work and sex mix?” – Because then it becomes a conflict of interest when you start schtupping your supervisor, no?

    “If I ever have occasion to go to an emergency room, I always ask the doctor, “is there anyone having sex in” – Maybe it’s just me, but whenever *I* have occasion to go to the ER, my thoughts are usually elsewhere. Namely things like, a.) Jesus, I hope they can reattach that finger or b.) Jesus, I hope they can reattach my friend’s finger. Sometimes it’s c.) Where’s that nurse with the morphine, my frickin’ finger hurts.

    “I find your candor remarkable.” – I find your bootlicking.. Well, remarkable, really.

    “because I also am a sassy bitch with a sensitive heart (which I believe you are, too)” – Nothing like making up an excuse for poor and/or narcissistic emotional behavior towards other people and wrapping it up in a cloak with the qualifying phrase, `sensitive heart’. See, reading this comment, you could also describe me as a `sassy bitch, with a sensitive heart’.

    “husband one and two were both found in work environments – where else does a working girl find them” – With a little luck, a `working girl’ won’t find them `on the job’. :)

    “After reading this post, having read all of your posts, I think if I ever met you in real life, it would be too hard to look you in the eyes without giggling.” – Seriously man, imagine that happening.. In real life, and think about it carefully. Do you REALLY want to be `that guy’? The giggling guy?

    “I know the rollercoaster wild-ride that your life is taking makes you feel alive, but does it make you happy?” – Aww, come on. EVERYBODY loves roller coasters. That’s `roller coaster’ by the way.

    “And there’s no way in hell I’m taking a woman who blogs about her sex/dating life in her *professional* blog seriously.” – That guy, he just took his damn toys.. and he LEFT. That’s what he did. Check it out. There he goes, leaving. With all his toys.

    “Twitter is evil, by the way.” – DON’T TOUCH IT MUM! DON’T TOUCH IT, IT’S EEEEEEVILLLLLL!

    “Then give them a true/false, multiple choice, and essay test. Evaluate, screen, and use as part of the decision to go from there.” – My god, I want to be your girlfriend. Seriously, you remind me of Hermes from Futurama. Do you make EVERYONE fill out a form like that?

    “I agree with anon. This post is raunchy” – I.. Uhhh. What, like `Debbie Does Dallas’ raunchy? What are you talking about?

    “You are not grounded, and that can be a destructive and dangerous thing to your reputation and your over-all quality of life. Throwing out the number of subscribers you have in conjunction with revealing your sexual escapades raises a serious red flag regarding your self-esteem and self-confidence.” – Hey pot? I got someone for you to meet over here. His name is `Kettle’.

    “She was cute, strange looking cute. And married. And pregnant. Then I went for another company” – I think that you can pretty much stop right there, because not only does the dysfunction shine like the northern lights in your response, but it also oddly reads like a, `Dear penthouse, this never happens to me but..’

    “Of course, D also could have been dating you for the Internet notoreity, in which case, good riddance.” – Ummmmmmm. didn’t Penelope just post about that, and how it’s OK to, `grow their brand’ or something? (I’ve got mental images of the Jolly Green Giant going on right now. I have absolutely no idea why. Maybe I’m jonesin’ for green beans or something.)

    “Okay, this just confused me. Do you want me to do you or not?” – Hi. 1976 called, and it wants both it’s pickup line and Camaro back.

    “Personally, I think more women should blog about what makes them tick bedroom-wise – that just sounds like a win-win situation to me. It’d be like having an instruction manual.” – Ladies and gentlemen, I present the laziest man in history. One who wishes no intimacy at all, and the answers to life’s questions to be dropped off, on a silver platter in front of him. Ian, dude. Half the fun in getting to know your significant other is LEARNING what turns them on. I would imagine that sex with you is a hurried, guilt-ridden and scary thing. WAIT! You can use a FORM!

    “You know, I’ve also had a boyfriend pee drunkenly on the carpet. MY carpet.” – I’m really glad that you indicated your severe indignation by specifying IN CAPS that it was SPECIFICALLY YOUR carpet. Those darned carpet-pissers.

    “It was a relationship that went about a year longer than it should have. And peeing on the carpet, as minute as it may seem” – It’s all about the carpet pissers, isn’t it? I’m wondering, did that rug really tie the room together?

    “Funny. In that shake head kind of way.” – Yeah. To me, this is about as unfunny in that shake-baby kind of way.

    “I too was worried when I read this.” – I too, was worried while reading your comment.

    “I don’t have a cognitive reason for my worry.” – I actually disagree, wholeheartedly. That or I do not think that word means, what you think it means.

    “You may have gotten yourself too deep into this all open all the time thing.” – She’s in too deep, capt! She’ll never make it out! (LPC, has it occurred to you that our favorite author is doing a St. Vitus Dance of self-destruction, and broadcasting it all `Christine Chubbuck’ style, due to some sort of insecurity, or other mental deficiency?

    “I have nothing but good wishes for you.” – No you don’t. You’ve got a guilt-trip, wrapped up in `mother knows best’ message for her. Just like a tasty, tasty bacon piece wrapped `round a scallop. A delicious scallop of dysfunction, that is.

    “posting private, intimate moments online will probably scare many a potential love interest away.” – Yes. `Probably’. Good word, there.

    “Am also a little aspbergers and neurotic and so I sort of “get it”…” – Ahh. The lesser-known, `Asp-bergers’. It’s when snakes are unable to communicate and relate to other snakes on a social level. Also, your post reeks of self-doubt with all the `sort of’ and `probably’. I think you’re mistaking snake syndrome for something else. Hiss.

    “I think that love really is just what he said- two people who happened to be in the same place at the same time and it turns out they fit really well together.” – OMG. You and that dude up there that was all like, “I require a pre-made instruction manual for all women I have sexual encounters with” need to get all hitched and have babies and stuff, ASAP.

    “But I hope he was hot and fun while it lasted.” – But he wasn’t. Because he was one of those carpet-pissers.

    “That’s just attention-seeking drama. That’s for lesser writers.” – Oh, I totally call shenanigans on you. It’s what ALL writers do. Lesser and.. Moorer. (Wait.. Hold on, there’s something wrong with that sentence.)

    “I’m always surprised with the “this blog sucks, I’m taking my ball and going home” and “what the hell is she thinking” comments.” – Indeed. How dare someone question what you consider to be gospel and verse. How DARE someone display an opinion contrary to what you believe in. Hey, check it out. You can see RUSSIA from your backyard.

    “P’s blog has always been a hyper-intimate introspective.” – Uhhhh. You’re missing the rest of that sentence, and also.. It just plain don’t make sense, yo.

    “P isn’t crazy, she’s just honest. Since most of us don’t have the balls to be that honest, perhaps we can lose a bit of the judgment and hand-wringing?” – You see, as screwed up as you sound, I actually agree with you, (with caveats.) P IS nuts. Really. But she posts what makes her LOOK nuts, and I `get it’ if I imagine that she is a performance art piece like Laurie Anderson or something. Also, aren’t YOU being kind of judgmental yourself?

    “She is the Founder of the largest social networking site for Gen Y professionals in the world.” – Since you’re using such loose terms, both I AND Mark Zuckerberg would beg to differ with you. Also, nice job capitalizing “founder”.

    “She consults regularly with She has spoken at” – Hold up.. Missing something there. See? This is why we can’t have nice things. That, or maybe you’re referring to some sort of female deity.

    “I don’t eat where I shit. Simple as that.” – That’s.. Uhh.. Awesome, man. Really. I am very.. very… proud of you.

    “While it’s easy for me to say that, given that I’m married and that I work in a traditional office,” – So, uhh. What, like, you shit in your office? Where you work?

    “and I am somewhat of an “expert” on this subject.” – I love people like you. Experts.

    “to having hot monkey sex with a stranger” – I not only love people like you, but I love expert people like you who use the term, `hot monkey sex’. I, personally would love to become an expert in `hot monkey sex’, but unfortunately seeing as how monkeys are sorta inclined to pulling the faces off of people these days..

    “regardless of how much money you have, your looks, brains or how much you weigh.” – I was following this, until I got past the `looks’ part and screeched full-stop into the, `how much you weigh’. A bit obviously transparent, eh?

    “But, you _are_ out of your mind.” – The only one line I completely agree with.

    “I love Ryan Paugh! But I don’t think he was right” – You know, I love Darth Vader, but I don’t think he was right to let Gov Tarkin blow up Alderan.

    “So I think you could have gone back to your hotel room with that guy the first night, gotten your charger..” – And gotten YOUR FREAK ON! (Or maybe just blown up Alderan.)

    “Maybe I’m selfish, but” – DING! Correct. No need to finish the remainder of your sentence.

    “I feel guilty that I am filled with such frissions of delight at reading the evidence of your spiral downwards.” – Goodness gracious! You sorta came FLYING out of the gate with that first sentence, what with `frissons’ and all that. Also, you misspelled `frissons’. Just an FYI.

    “Is it an atavistic response to perceived hubris?” – Ok, now you’re just using 25-cent words for no other purpose than using 25-cent words. You’re becoming `that guy’, the dork-with-a-thesaurus dude.

    “This is the last straw for me. If I want Carrie Bradshaw” – But she’s not even Carrie Bradshaw. At least Carrie could write. And had great taste in shoes.

    “I don’t think you have asperger's syndrome since you are really good at communicating and you like parties.” – Without a doubt, this is my favorite sentence in the whole thing. I can tell you, that Leslie is exactly right. That’s word-for-word how it’s written in the DSM-IV diagnostic guide. `Should patient profess an uncanny love of parties, disregard diagnosis.’

    “it’s unprofessional. And honestly? Kind of gross” – Yeah, let’s keep sex behind closed doors, in the dark and by god, let’s all write manuals, for chrissake.

    “Its good to know your as crazy as every female Ive ever known.” – Hey now! She’s not the one pissing on carpets here. Also, PLEASE LEARN HOW TO USE `your/you’re’, etc. I swear, when people do that, it just makes my heart give an atavistic hubris response. FRISSONS! ASP-BERGERS!

    “I actually don’t think this post has to do at all with work and dating.” – I agree. I think it’s nothing but drama for drama’s sake.

    “so someone told me to read your blog because it sometimes reminded them of me. now I know why! Love it!” – A quick translation, “I am making a post, about myself! That nobody understands! But me! This is all about ME! ME, ME! Me, me? ME!”

    “Take love (in whatever form) where you find it. Do what seems right to you.” – But, you gotta like.. Watch out for that brown acid, man!

    “Honestly, I would say that the way you write has forced me to become oddly attracted to you,” – And this is where the crazies start to come out. Actually, no. The `I’m so attracted to you’ crazies started coming out wayyyyyy above this comment.

    “And I’m not a weirdo.” – My second-favorite sentence in this. Dude, the rule of thumb goes that when people feel compelled to say, “I’m not a weirdo”, uhhh.. Well, generally, they are.

    “I think she would probably know more about the condition and its symptoms than most people.” – I know a guy who has cancer. As a result, I like to go around and diagnose people with cancer. I know more about cancer than most people, so I can tell if I have cancer. Or you. Hey, by the way. You have cancer.

    Ok. You don’t have cancer.

    • Maus
      Maus says:

      >>”I have nothing but good wishes for you.” – No you don’t. You’ve got a guilt-trip, wrapped up in `mother knows best’ message for her. Just like a tasty, tasty bacon piece wrapped `round a scallop. A delicious scallop of dysfunction, that is.

      Seriously, dude, you are hilarious. “Scallop of dysfunction” is my new favorite metaphor.

  12. Liz
    Liz says:

    I’m not sure this will make sense in an obvious, direct way, but I think the lesson is, ‘Don’t try to make people you are dating do things.” People’s actions are information. If you get involved in the process, you throw it off balance in a way that makes nice people uncomfortable, and controlling people way too comfortable.

    The young guy always talked past you, and tried to make you do things you didn’t necessarily want to do, right from the start. Then you tried to make him do things too because it seemed to make sense that you would get a turn. Then he pushed back, because that’s the game. And eventually you end up arguing about the oral sex you’re not getting in a hotel room with a pee spot on the floor.

    The nicer guy just accepted you, and worked around it. It sounds a lot nicer. But then you tried to get him to do something for you, and he basically said that was uncomfortable, and he didn’t play the game with you.

    This probably doesn’t make sense, but I don’t necessarily have the words to explain the interaction that I’m recognizing.

  13. Liz
    Liz says:

    Anyway, it has nothing to do with work. It’s the interaction, not the way you met them, that makes the difference.

  14. Grace
    Grace says:

    Let’s all be realistic. We came for the career advise but we stay for the for the smut. Fun for me, but I wouldn’t invest in it.

    As captivating as a car crash. Between Dellifield and the oral sex freak out, I’m officially with the “worried” crowd.

    Penelope, get focused. Just like taking an extended time out to live out on your parent’s couch can bring clarity, so can a time out from relationships. Get a good vibrator. Be alone for a while.

  15. Mickey Van Roo
    Mickey Van Roo says:


    Any chance you could put some video (you know, the amateur soft core kind) with the written verse? I’d luv it and think of how many eyeballs would come to the site.

  16. Nancy
    Nancy says:

    I’m a person married to an Aspie, and mother of another Aspie.

    I found this post kind of sweet. Aspies are great.

    You go, girl.

  17. Brazen Idiot
    Brazen Idiot says:

    I have been reading this blog for a while now but this just made me log into my news feeds and manually click ‘delete’.

    You talk about being around people who are younger than you but by writing this you have shown yourself to have the mental capacity of a child.

    I think you should seek intensive therapy and look into some of the medications out there, that is, if you are not already on a multitude of uppers and downers.

    Good look with your life and I hope one day you realize what life is all about. Get out of your pathetic blog, turn off your cellphone and laptop and get a grip on reality b1tch!

  18. Jennifer Lynn
    Jennifer Lynn says:

    Hi Penelope,

    You ask whether you should date people you meet on from the blog. I think that’s the wrong question. In my opinion the problem lies not with the medium you use to meet people, but rather in they type of guy who is likely to pursue you. Take the “charger” guy, for instance. There are only a few types of men who will respond positively to “Are you trying to date me?” right at the jump. Either they appreciate your quirkiness or there is something so weird about them that they are willing to put up with generally weird stuff from you. Don’t get me wrong, I think you are delightful, but your behavior might cause your suitors to self-select to a pretty strange group, with a high percentage of “oh-okay-there’s-a-very-good-reason-this-guy-is-single” people.

    You are so good at self-awareness in your professional life. You have made small, necessary adjustments to your instinctual behaviors so that you can make a decent first impression on the types of people whose professional company you’d like (and you’ve encourages your readers to do the same). Then, you are totally yourself later and everyone already loves you. Perhaps you could try that with relationships. I’m not saying change who you are, just share a different side of yourself in the beginning.

  19. Wil Butler
    Wil Butler says:

    I’ve often wondered this myself, though there seems to be plenty of examples on either side of the argument. There’s the people who met at work, fell in love, and got married. Then there’s the people who met at work, dated, found out they hate eachother, and ended up with a really uncomfortable work place.

    Also, maybe you just need to find better quality guys if the ones you end up with piss on your floor and you need to demand oral sex out of them.

    Are there really people who refuse to go down anymore? I thought it was pretty much a standard part of foreplay now.

  20. Jeff
    Jeff says:

    No wonder your husband left you! Are you seriously that desperate that you’d sleep with a urinating adolescent you met on a blog?

    There’s women like you at our office and they repel men like giant dancing vagina’s.


  21. Kerry
    Kerry says:

    I’ve never seen a giant dancing vagina. That’s very interesting.

    They repel men, you say? All men, or just the assholes? Where can I get one of these?

  22. Jim Derk
    Jim Derk says:

    You’re clearly a mess. I don’t see things working out for you in the long run. Good luck though.

  23. Jessica
    Jessica says:

    I think if you haven’t met anyone not through your blog you should go out for drinks with girlfriends to a club.. or maybe join a dating service… or maybe go dancing or for a walk in the park..

  24. Sara
    Sara says:

    Jafo – you made me laugh out loud – thanks!

    What Penelope needs is a man – I mean seriously. She keeps dating people she doesn’t really respect. I think it’s actually a defensive mechanism – she thinks she’s “dominating” the relationship. Think of all the posts about I have more money, I’m more successful, yada, yada, yada. Even the fixation with oral sex is a red flag. I enjoy it as much as the next girl, but come on. If you’re using the equipment right, it doesn’t hold a candle.

  25. jrenee
    jrenee says:

    first of all: work and dating can mix; I met my husband on the cafeteria line (on-line!)
    but then I wouldn’t actually date him till that job ended (was a summer contract)

    i found him because I wasn’t looking; I was working on myself.

    and then I spent all summer getting to know him (I said no to dates, but I suggested having lunch together instead; which we did every day that summer :)

    I suggest you stop looking for men and for sex. work on yourself; realize what you need in a relationship.
    spend time with your kids.

    i know this advice isn’t exciting; but then your latest excitement doesn’t sound like much fun.

  26. Top
    Top says:

    At first I thought…is this question serious? Of course it DOES NOT work to mix dating and work. However, the reality is that that is where most people spend most of their time. So, the true advice is this…if you are really interested in someone, and its reciprocal, go for it. But, if you just want a one night stand, hit the bars or somewhere similar!

  27. andrea
    andrea says:

    I don’t even get how this post is about mixing work and dating, except in the most marginal sense.

  28. Poochie
    Poochie says:

    I’m can’t even understand why you blog about a post on oral sex or personal sex escapade. This kind of post will only backfire. Good luck.

  29. Tim Mitchell
    Tim Mitchell says:

    Dating is bad news at work! I know I met my wife in an office and it was weird going to work and meeting you other half but going off in different directions in the evenings.

    If you had a row everybody in the office would know about it. The bosses said it was affecting our work, which just wasn’t true. We both changed jobs and were married a year later. We have now been married for nearly 11 years and have a little daughter.


  30. Alfred
    Alfred says:

    I stumbled across this blog.
    Narcissistic, arrogant and repulsively self-absorbed.
    The gentleman who told you to “get a life” gave good advice.
    Good luck with your life, I hope you perhaps become more humble and down to earth and learn to treat human beings with less contempt.

  31. Bob
    Bob says:

    Spare a thought for your children who will grow up and read the very public and graphic details of their mommy’s promiscuous escapades.

  32. Brett Staupe
    Brett Staupe says:

    It’s hard to judge whether dating coworkers is a good idea. One can reason that if they were able to get the job in the first place (my job being so regulated it’s scary), that they must be mature enough to handle a responsible relationship.

    But if things go sour, as over 50% do, one needs to have an exit strategy. Think: Can I get another job quickly if I can’t work here? Or is he/she in a totally different department that doesn’t affect my work. Cause if it does, and you answer no to the first, and yes to the second, not the other way around, then don’t proceed with the relationship.

  33. mark branham
    mark branham says:

    Ha, I was right. When I divorced I was determined to never date an American girl. Fortunately I live in chicago so I didn’t have to. You have proved how right I was… you seem to treat sex as like an after dinner drink. And the farmer took you back? Americans!!!

    Ya’ I dated 4 women and not one was native american. Been with my latest 4 years now, I’m grateful I learned my lesson, no matter how late in life.

  34. Michelle
    Michelle says:

    I love reading your personal stories on the blog!
    You are honest and funny and real.
    I will never understand why people read this and
    then complain. So stupid.
    I wish you would write another blog just about the personal stuff!


  35. Jonha
    Jonha says:

    Hi Penelope,

    I would NEVER ever mention about you on my tweets, ever. At least I’ll try. I don’t want to be branded as a stalker too. The only difference about me and you is that no one stalked me, so I figure I do the stalking. Ok so this comment is a little messed up.

    I think it’s a little difficult for you to walk and talk with anyone because people would start talking about it but I like just how careless you could be at times. Sometimes you have to listen to your heart though, not all people come up to you just to use you. I like the courage of the 25-year-old, I think we should meet instead, lol.


  36. Linda
    Linda says:

    I think you can mix them as long as you’re careful. I was a bit wary of doing it myself, but the key is to take it slow. The best tips I’ve read are in an ebook called The Go-Getter’s Guide to Finding Your Soulmate. But before you act make sure to really think about your situation.

  37. Deanna Thompson
    Deanna Thompson says:

    Suddenly I don’t feel so alone :) It is totally great to hear some honesty about the dating world and such. I’ve had a few bizarre stories of my own. Quite frankly I’d never mix dating and work but then again, no one I work with interests me….yet!

  38. Jason
    Jason says:

    Wage slaves dating wage slaves. It sure is a fine site to see a young couple wearing the same oil change uniform walking down the aisle at a grocery store. How anyone could be thinking about relationships inside such a beleaguering environment is beyond me. Capital-ism and they still cannot create and manage their own type of social phenomenon. How many men just love pitching a tent at the copy machine when an attractive co-worker skims by in that type of environment? Basically, I don’t care if you’re on your own either. It’s laziness to just follow the primitive social constructs. It’s no wonder we have such mundane lives relative to what they could and probably should be. Yes, many relationships got started at work, but most were out of monetary reasons, general frustration, shyness, and being lonely. Gee….was that all because…..I wonder….that fact that they’re at their #$(!ing job all day long with no time to do anything else?

    So, we all work too fuck@(! much and you women….leave work be work.

    Ya’ll are sick

  39. Racer X
    Racer X says:

    “But really, there must be a ton of people who think sex and work overlap because, look, my blog has 33,000 subscribers.”

    Yes, sex and work overlap, or rather, the working world and the erotic world overlap, because they are both made of people, and whenever people get together, eroticism and sex follow. In our puritanical culture that is considered a bad thing so, so people feel they have to keep it a hidden, dirty secret.

    And the 25 year old should have gone down on you, but like most 25 year olds, he probably did not know too much about women.

  40. Daniel
    Daniel says:

    This needs some seasoning from a young (gen whatever) who has had sex with and dated someone from the workplace. I’m 27 now, but I was 24 back when this was all happening. Simpler times I suppose. Anyway there is something to be said about dating someone from the workplace but my situation was a little different.
    I was a co founder of a dot-com and that is in it’s own right something to be proud of in a seriously economically injured state (Michigan) even back in 08 when this happened. Bravery I guess. My co founder and I pretty much made our own slice of Silicon Valley at our first office. When you’re 24 and hire your first employee and go through everything from picking out the paint, to making your own lunch times, paying your friends, rent, and trying to keep a 20×5 whiteboard manageable with a bunch of other 20 somethings, it isn’t a walk in the park. Unfortunately, you don’t get that kind of slap in the face from reality until a few offices later, but that’s for another time.
    Back to my original point, there was a cute employee programmer we hired on. Things went fast. She was 19 I was 24, we liked each other. After a party where I had originally met her to get to know her (it was actually my friend who invited her intending to date her but that’s for another time) we started to get to know each other, and started to get into each other. It took about a good solid month to make sure we were each good to go in the single department and actually wanted to date, but suffice it to say, we started to date.
    It was a good relationship in the beginning and I was even getting her to stop smoking (she only smoke because she was mildly stressed out and they were only clove cigarettes) We got along well and the god times flowed and most of the time we actually had something in common, which made our subsequent relationship solid. We would generally bring it up and she’d come over to my office and we’d hangout/work/”be together” for a while. Sometimes before work is done, sometimes after as a reward. A reward to me more than her, but that’s beside the point. It’s these moments is where making sure that “freshness” and “newness” is a constant.
    What I learned is basically a few facts that boil down to getting something out of the relationship.
    1) You don’t know what you want until it’s presented to you. Even if you do, when you’re in the heat of the moment/with her, at least in the beginning, you don’t care what is on the plate. This was more age related and I’m sure now at 27/28 I would still think this way given that I was a late bloomer to the world of girls. But bottom line, pay attention to your taste. Inside and out. Especially on the latter.
    2) Waiting for her to be okay and calmed down from a previous relationship where she was pretty much lightly battered by her ex to start dating you is not okay. Among other things, she wasn’t ready to be called a “girlfriend” again. People who wait for other people to be okay better be damn sure that that person it worth it. Seriously, people. This is someone you’re wanting to be exclusive with. Fucking take a minute and think about what you’re waiting for.
    3) Just because you pay her, doesn’t mean she’s anymore yours than an employee of another company is to them. This was a longer term beating in the head. Day to day operations needed to have something that ebbs and flows. In other words, I had a work with your wife relationship way way I actually should have. If I even should’ve at all to begin with. This is a tough one because you have to make sure that A) She stays busy and you can keep your co founder off your back by making sure she stays off Facebook and browsing is actually work related and helpful, (and maybe more importantly) B) Making sure you can pay her so she has a job and you don’t feel like a giant failure. Not being able to pay your girlfriend in your own company is the corporate equivalent of pretty much asking a dogs jaw to go at your nuts and knowing you deserve it. It sucks in more ways that than too. It carries to reputation from your friends and family and) in my case at least) it gets your businessman father to nod his head in shame over what you fucked up on. Then there is the obvious bedroom issues where you have to see her complaining about not being able to put gas in her car and eventually wanting to get another job.

    It ended mutually and very well actually, but it was still kind of hard to stomach during the downturn and eventualities. My advice to you? If you’re going to go for it and date someone, make sure that you don’t control her paycheck and/or that both of you are on the same jobs levels. And for crying out loud please be careful.

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