How to shift between work and dating

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Here is a map of where all the single men are:

I do not live near any single men. Well, I sort of do. My divorce lawyer has set me up with a few men in my hometown, Madison, Wisconsin. He told me that I am too focused on my work life. I need to get my personal life in order.

Here’s how things went:

One guy was a little chunky in the middle, but he is a real estate mogul. I know, you’re thinking, real estate mogul, in Wisconsin? Are there any? There are a few. I mean, Lake Michigan is a nice place in the summer, and also, someone’s gotta own the real estate around the Green Bay Packers stadium. And besides, you can invest in real estate from any state, really.

So I went out with the real estate guy. He said right away that he wants to diversify, and I thought right away that I’d get him to fund my company. But before I could move in for the kill, I started falling for him. Which was very bad because I did not have my dating pitch set. Only my company pitch. And, he actually said to me, “You need a better pitch.” About my marriage. He said that. He said I need to explain in a quick way what happened with the marriage.

I told him that I think that my husband probably has Asperger syndrome, and, hell, probably I do, too. And we are the marriage of varying degrees of social awkwardness. I told him that’s why I think our marriage fell apart.

That did not go well.

Fortunately, in a town like Madison, all the rich guys go to the same divorce lawyer, so my lawyer had another idea. A furniture store owner.

I was like, “DUH! Do you not see my income in these divorce papers? I cannot date a furniture salesman because maybe I’ll fall in love and marry him and he’ll stop working and then divorce me and I’ll be supporting two men for the rest of my life and still not be having sex.”

The divorce lawyer is a guy who can withstand many hysterical fits in one day probably because he charges hourly for them but also because it comes with the territory when you are helping people get through the worst time in their lives and they need someone to blame for it. So he said, “It’s not just furniture. He owns every furniture store in the state.”

I said I’d consider it. And while I was waiting for the divorce negotiations to kick into high gear, I noticed that all furniture delivery trucks have the guy’s name on them. Like there is a furniture monopoly in Madison or something.

So I called him. And then I got this idea.

I had this radio show in Madison but I didn’t like doing it because it really doesn’t help my blog. So I stopped doing it because local radio is local and internet is not local. But then I thought that I could get this guy to give me a new dining room set if I could say his name on the radio during my show. Like, product placement. And then I started fantasizing about my dates with him and at the end of a great night of marketing discussions and drunk flirting, we would end up putting great furniture inside a truck with his name on it and drive it to my house.

That’s the problem with all my dating. I can’t stop letting my mind turn it into a business transaction. I thought for a second that I had changed my ways when I finally got a guy into bed. After missing just about every cue he gave me over the course of almost two days. So there we were in bed, but I realized that he’s got all this great information about recruiting, and my company, which is actually in recruiting, could benefit from that.

So I asked him how candidates differentiate themselves.

He said, What?

Then he said that the best candidates never let anyone know they are looking. They just let people know what they’re great at.

We talked and then I was happy that I had something to write about and I fell asleep in his arms.

This is how I know I better move to a place that has more single men. Because look, I’ve gone through three already and not been able to stay focused on the non-work part of things. I need more chances to figure out how to separate my work life and my personal life. I am not totally sure how to do it.

Am I the only woman with this problem? Don’t most women spend the majority of their time with men in a work situation? And don’t most women train themselves to not do dating when it’s time to do work? So how do we retrain ourselves? I am so good at figuring out how to do business with every guy I meet. How does this translate on a date?

152 replies
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  1. Alan Wilensky
    Alan Wilensky says:

    If more marriages were run likes businesses, we’d have fewer divorces. The best is when two self employed spouses can help each other with strategic advice and vision, and then blow off steam in bed.

    Actually bed is the worst place; bed is for sleep. Make love on the floor. Memory foam pad full size for just that purpose of love. calico coverlet.

    • Angela
      Angela says:

      They did a study of women and asked women what they really wanted to do in bed. Most women really would like to get more SLEEP when they are in bed.

      This is probably tied to the rush-rush-rush overstressed lifestyle that most women live. I don’t know how women who are wives and mothers, as well as work outside the home, do everything they do.

  2. Joe Fusco
    Joe Fusco says:

    When you stop looking at your work life to supply your identity, your security, your control, your fun and your sense of belonging — you’ll begin to build a satisfying, distinct personal life.

  3. Angie
    Angie says:

    I love what he said about candidates just letting people know what they’re great at. Good advice, provided you’re able to meet people who can offer you something you’d like to do.

    I think I have a similar problem to yours in that I’m constantly networking. As soon as I meet someone new, there’s this little filofax in my head that spins until it comes up with something: Tom Smith, builds custom amps. And then out of my mouth: “You’re a jazz guitarist? How cool. I know this guy who builds custom amps if you ever needed something . . .”

    But I realized at some point that this is less of an effort at networking – although I love to help people out and get people together – and more of an effort to find something in common with the person. That’s how women establish rapport in our culture. Once I realized that that’s why I did it, I was able to look more objectively at whether the “connection” was really something worth mentioning — and I also was able to listen more so that I would learn more about the person, rather than seize on the first thing I could.

    Maybe for you it’s as simple as setting conscience boundaries for yourself when you go on dates, and then making yourself stick to them (I will focus on getting to know this person. I will not think about business.). It’s like giving yourself permission to relax.

    • The Office Newb
      The Office Newb says:

      I agree that we all have ways of trying to make instant connections. I find that when I meet a new woman, I will compliment her on her shoes/outfit/handbag. I don’t consciously do it and I don’t lie about liking something but it’s one of the best ways I’ve found to create a “common ground” with a stranger.

    • Angie
      Angie says:

      Can’t believe I’m responding to my own comment, but I must because I’m an editor. I meant “conscious”, not “conscience.” Oy.

  4. priscilla
    priscilla says:

    try this. instead of figuring out what you can get out of all the guys you go out with, choose to use the time spent with them to appreciate them, their looks, their interests, their values, and what they give back to the world. it means focusing all of your attention on them instead of trying to get equal billing as you would in a business meeting.

    i think you’ll probably score.

  5. joe
    joe says:

    Please, dearest Penelope. Give yourself a break from men. You are a relationship hopper and it is a form of escape from yourself. You need to get get right with who you are before you invite anyone else in.

    Your posts are an open book into your soul and it is obvious that you’ve got issues (as we all do).

    Please give yourself a good year at least of not even thinking about dating.

    • Lane
      Lane says:

      You know, I completely don’t agree with this. One finds out more about themselves in interacting with others. I know the common prescription is “time alone, figuring yourself out” but from experience, that feels like avoidance and one-stop-shopping. Penelope will figure out what is best for her as she does it – through experiencing.

      Perhaps I’m sensitive – after a divorce or a relationship break up, people often give the “time to yourself” advice. But reality is this: you learn more about yourself when you are interacting with other people than you ever do sitting on a mountaintop.

      • Bethany
        Bethany says:

        There’s a difference between time alone and time not dating. After I had a bad breakup I made a conscious choice not to date for awhile but I also increased my volunteering, joined a riding class, and began a weekly dinner with friends. I made great friends, learned how to do things I didn’t think I could, discovered the careeer area I truly want, and yes, did eventually end up dating a fantastic guy I met at the first friend dinner. I’m glad though that I didn’t try to date him when we first met, I had too much else to learn about myself without locking myself into one person.

      • Katherine
        Katherine says:

        You must be an extrovert – in which case, I would say it’s good advice for people who are energized by other people, but horrible advice for introverts.

    • Sean
      Sean says:

      Judgemental, much? First of all, I don’t think P is a relationship hopper, she’s dating. Dating is a healthy thing. We all do it. It’s normal to want to find a connection with someone beyond the mundane business relationships or friendships. Taking a year off from dating is the worst possible advice anyone can give… obviously the purpose of this article is to find a balance between dating and worklife. Eliminating the dating aspect doesn’t seem like balance to me.

      • Bethany
        Bethany says:

        Actually in response to Katherine (it won’t let me nest, sorry!). To be honest, I’m terrified when I meet new people and forcing myself to interact on a social level with new people is one of the hardest tasks I’ve ever tried. However, I can talk to people when I have a purpose (advice on animals, what food to order, etc) which helps me get over my natural tendency toward shyness. I think it’s good to try and scare myself every now and then and not let my nature win. If I don’t push past my comfort zone I’ll never grow.

    • Holly Hoffman
      Holly Hoffman says:

      I’ve been on a no-relationships sequester for the past two months with four more to go. I’m a serial monogamist, so it’s been difficult, but very eye-opening. Maybe it’s not bad advice to give it a break for a while. I’ve learned a lot about what I really want and need already, and literally each week I spend alone, the more that evolves and reveals itself to me.

    • Helen
      Helen says:

      I soooooooooo agree with Joe. Give yourself some time to heal from the divorce and from the Farmer. I would suggest you spend time with JUST YOU(this may come after work, phone calls, kiddos, and whatever else), but my point is, take some time. And no, I’m not recommending you sit on a mountaintop or isolate yourself, just pull back a little and put the dating/men/”what am I doing wrong” thing on the side burner for a little while.

      You deserve the “best” you!

  6. D.
    D. says:

    As for separating business and dating, my mom is currently dating her business partner. How’s that, huh? ;-)

  7. KMS
    KMS says:

    LOL – at least I’m not the only woman who does this. You get so in the habit of work that it’s hard to break it when it comes time for fun. Autopilot kicks in.

    If you figure out how to break, please let the rest of know how you did it!

  8. Froggylou2
    Froggylou2 says:

    To answer your question, no I do not spend a majority of my time with men in a work situation. I am lucky to have a good balance of female and male friends that I get socialize with frequently. I could easily get wrapped up in my two jobs, volunteering, etc., but I choose to make time for a personal life. I refuse to let my life slip by while I try to get ahead for a company that will probably dump me when I earn too much.

    To your other question regarding no dating when it’s time to work, I’ve done that. I would get very focused and wouldn’t allow time for dating. But then I would see some female and male executives with no life but work. My mother is like this. I don’t want to be like that. So to answer your third question regarding retraining ourselves- you betcha I did. I had to learn how to balance it out. I’m still learning.

    My opinion, take more time for yourself and your kids away from work. You’ll learn how to just relax and not think of life as a “pitch.” Take time to enjoy the present day. It’s the only thing that is certain.

    I live in Wisconsin, too and this not the best state for singles. However, here’s a little bit of hope. I read in the Journal Sentinel last week that in the Milwaukee area there are around 244,000 single people.

  9. Joselle
    Joselle says:

    “Then he said that the best candidates never let anyone know they are looking. They just let people know what they’re great at.”

    You’ve got your answer right there (I think you probably know that, though). And I would add, they are also good and finding out what the other person is great at and letting them know.

    To focus on relating to men as dates and not as business transactions, you cannot move. The problem is not where you live. If you move to another city, you’ll face this problem even more because you’ll meet a greater number of business-oriented men.

    Perhaps you have a lot going on with your company, your recent divorce, and your family and you don’t have space in your head to find another guy endlessly fascinating. That would be okay too.

    Why do you want to date? Other than sex, what do you want from it? Maybe getting clearer on that will give you some answers on how to date effectively.

  10. That Mike
    That Mike says:

    For every moment you settle for hopelessly short-term situations like this, you are not with someone that appreciates your beautiful, sexy, funny, clever, eccentric and quirky being.

    Being reminded every time you sit in the dining room for a family meal that you gave away some of your intimacy for that furniture isn’t the long-term and strategic thinking I would expect from you.

    Your thinking might seem to be effective bartering but little by little you are giving away Penelope far too cheaply. He’s thinking wholesale cost, you’re thinking retail value.

  11. Voice in the Crowd
    Voice in the Crowd says:

    I have to agree with the commenter upthread. You define yourself with your job. Every aspect of your life HAS to relate, in some way, to your job, and you’re brain is making you look for Significant others like you’d look for an employee, what can this person bring to the equation, and not in an emotional way, but in furniture, or money, or business advice.

    I understand that running a start up is similar to drinking molten lead, and that when it’s your money on the line work never ends. But you need to set limits, boundaries, or at least a closing time. You mentioned in a post that being your own boss means you get to tuck your kids in at night, but after they’re tucked in, what are you doing? Are you reading a book for fun, watching some cheesy movie, writing for no one other than yourself, talking on the phone with a friend about random things other than work, or are you right back at the job as soon as you close the kids door.

    You need to decompress, your brain is full or work and nothing but work. You haven’t let it think about anything BUT work in years, and so it’s trained to relate everything you do or think about to work, what else does it have to draw on.

    One week, be home in time to feed your kids dinner (not saying you don’t feed your kids or anything, but if I just said dinner, you’d eat dinner at 10pm), turn off your cell phone, shut down your e-mail, and just relax, watch TV, read the newspaper other than the business section. Find some part of Penelope that isn’t related to work.

  12. Greenman2001
    Greenman2001 says:

    I’m a little confused about exactly what the problem is that you’re trying to solve. Is the problem that men lose interest in you? Is the problem that you can’t find men you’re attracted to beyond getting laid or talking about business? Is the problem that there is no place for a relationship in your life? Is the problem that you don’t want a relationship but are using “a relationship” as a tool to get other needs met? You’re a businesswoman: treat it like a business problem. What’s the problem, what’s the goal, what’s the plan, what are the metrics, how will you know the plan is working, what will you do when the plan fails, et cetera. When you make statements like, “I need more chances to figure out how to separate my work life and my personal life,” I feel like you’ve answered an irrelevant question for yourself. What makes you think that separating your work life from your personal life is going to solve the funamental problem you’re up against, whatever that problem is?

  13. Lane
    Lane says:

    Just the feeling I get from reading this blog post:

    I really think that your mind is focused on work because that’s the most pressing detail right now. Your divorce is final. You actually have a quality relationship with your ex. Your kids are happy and doing well. The thing that is the least “under control” is the business, and in a way, that relates directly to your feelings of self-worth as a single woman. Right now, your business IS your personal life.

    Perhaps instead of listening to everyone saying “take some time away”, you need to actually give business MORE time. If it is inserting itself into all aspects of your life, usually that says that you feel as if something is unfinished. Can you go finish it? Can you send the kids to dad’s for a weekend and dedicate yourself heart and soul to working on the nagging problem?

    I’m not trying to say you don’t give your business enough time. I’m trying to say that perhaps it needs a little focused, uninterrupted time on a few issues. And then, maybe it’ll stop hijacking the rest of your life. Focus that unsatiated sexual energy at the business for a bit, and it might free up your mind for non-business pursuits.

    Just a thought.

  14. Jerry
    Jerry says:

    I’m not an editor nor do I have a degree in composition, but…

    1) I believe home town is one word (at least according to the boss, it’s one word).

    2) Shouldn’t there be a “be” before having sex in this statement?

    “I cannot date a furniture salesman because maybe I’ll fall in love and marry him and he’ll stop working and then divorce me and I’ll be supporting two men for the rest of my life and still not having sex.”

    3) I don’t think you’ll find the type of man you’re looking for in Madison. So, yes, you should move.

  15. Janet
    Janet says:

    Having been through a divorce and 5 years of dating, I identify with your plight! Dating was just networking and business, even when there was romantic potential.

    My favorite is how I helped my techie “boyfriend” find an exec level job by teaching him about SEO. That was what cinched the deal on the first interview. That more than paid for the $400 he spent on my hair that he ended up hating anyway and that I dumped him over. But he’s richer for having dated me. Another man said my internet marketing advice improved his business – and he quantified it by how much. Can I use that on a resume??

    I went through a phase of dating to get guys to help me with my businesses. Do things for me for free. It worked really well. But I usually ended up doing just as much in return by teaching them things they needed to know.

    I also dated successful businessmen who I could rely on even after we dated. I called them for business advice.

    My favorite is the millionaire who cried on our first date because he was lonely, and tried to get me to spend the night with him in a sly way. He also asked if I wanted to get married. That was the end of that.

    Eventually I decided if I wanted a relationship, I needed to make room. So I started clearing space. Literally and personally. I made friends with women and built a social life with people who cared little about business. When dating didn’t go well, they were still there.

    Basically you avoid emotional risk when you make it all business. It’s safer. But you grow out of it (or at least I did). Then you decide it’s worth risking for closeness.

    Almost every divorced woman I know dated defensively by hiding behind something. Until they were ready to have real relationships. Usually several years later.

    So it’s pretty normal. I hope you find funding, good advice, and a great network of successful men because of your dating life. Sounds like you’re choosing well, so keep going. Don’t limit yourself to locals either. When you travel, set up dates by networking. It’s a great way to see a new city. Ever thought of trying internet dating – you’d have hilarious fodder for your blog.

    This is already too long.


    • Lane
      Lane says:

      See, and I’d say I married defensively by hiding behind something, and got divorced when I was ready to have a real relationship. I just didn’t know it at the time. And I relate to helping put all my partners into a better financial space.

      I think you have some interesting insights in your comment.

  16. KateNonymous
    KateNonymous says:

    Maybe if your dating pattern isn’t going well, you need to change the pattern by not dating.

    Maybe you need something in your life that’s about Penelope and not about work or sex or other people.

    Maybe you need something in your life that has nothing to do with Penelope, but is entirely about other people, like feeding the homeless or volunteering for Meals on Wheels.

    Maybe you need to move. Maybe you need to stop talking about moving and commit to living where you are as part of the community.

    Maybe your divorce lawyer is setting you up because on some level he wants you to get married, get divorced, and provide him with more business.

    Mostly, though, maybe you need a new–or at least more complete–source of information. For example, the map shows more men than women in the L.A. area. That wasn’t the case as of the last census. Yes, it’s been a while since the last census. True. But the reason for a change (if indeed there has been one) is because of birthrates. That’s right, in a lot of places there are more men than women. Under the age of 25.

  17. Frank B
    Frank B says:

    “Then he said that the best candidates never let anyone know they are looking. They just let people know what they’re great at.” – Best pillow talk line I’ve heard in a while!

  18. Cor
    Cor says:

    Saw your comment on twitter–I follow you there & was going to DM you but you’re not following me. Just wanted to say that I liked this post and forwarded it to a single friend of mine–with a great sense of humor–who has started her own small business.

  19. Kera
    Kera says:

    As harsh as it sounds, there is a great deal of scapegoating going on in your reasons for having unsuccessful dates. The solution isn’t to move to where there are more men. If you have already identified that you turn dating into a business transaction, what good will moving do? It won’t make your mind think differently. The change will come when you stop identifying yourself by your job. You gave up the radio not because you didn’t like it, but because it didn’t benefit this site. When you described to the real estate mogul why your marriage didn’t work, you didn’t say that you two couldn’t work things out, you said that Asperger’s caused you to be unable to work it out. You asked for business advice post-coitus.

    A new location will not be the solution. Whatever is already in your mind will follow you to any place you visit. The only way to move forward is to change your thinking. Turn off the computer for a day, take a bubble bath and read a book for pleasure, go to a museum and enjoy the artwork (turn off your phone first!). There is so much more you can do to improve your situation than to immediately escape. Try that first.

  20. Dan
    Dan says:

    My brother is single, around your age, and lives in Madison. But he’s a weirdo. And far from rich.

    It’s tough anywhere to find singles over 40 who don’t have issues. Maybe you need to try a Demi-Ashton thing.

  21. Victoria
    Victoria says:

    Penelope- maybe change isn’t the answer. Perhaps it’s just finding the person who also approaches every situation in life with the potential for business. There’s nothing wrong with that! In fact, my boyfriend and I work together well because we approach our life together from a business perspective, and we each have strengths that the other doesn’t have. So he helps me with the economic side of business, and I help him market himself at work toward promotions and raises.

    It’s not you, it’s men. I know that’s a crap thing to say, but hey, they’re total pigs so just find a clean, nice pig who lets you be who you want to be.

    • kaycee
      kaycee says:

      Exactly. What you should do is go out on the schmooze circuit — give talks at exec conferences, etc. — and find some cute, young, single Silicon Valley venture capitalist or angel investor (or have Guy Kawasaki fix you up. Then start a long-distance relationship both enhances & leaves you plenty of time for your business.

      As for the take a year off stuff: That’s what I did after my big break up(s). I found that all that introspection led me to kinda lose my social skills. Once I was ready to date again, it was really hard (whereas when I first broke up, there were LOTS of guys interviewing for the new boyfriend job.)

  22. David
    David says:

    Reason #546 why I heart NYC – my chances of meeting a great single girl greatly improves!

    I hate to say it, but I think demographics really do play an important role here. I have to believe that your luck would greatly improve if your “single men dating pool” is widened. You may like living in the Cheese State, but your love life may be asking you to try settling elsewhere for awhile and see what happens. And if moving isn’t an option due to your business, well then try making a little “you time” and do some traveling. Hell, you could even make it business travel, snag a man and pack him in your bag for the ride home.

    And if you meet Mr. Right somewhere else, you could always talk him into moving back to Wisconsin with you! Or as I said above, just stuff him in your carry-on bag and take him against his will. That probably works too. :)

    Whatever you choose to do, I wish you luck!

  23. Seth Simonds
    Seth Simonds says:

    Who says you need to separate your work life from your personal life? You’re passionate about your work. Why not stop trying to change your dating style and embrace it? There are plenty of wonderful and successful guys out there who’d get a kick out of discussing spreadsheets between the sheets. Look for one of those. If you don’t, chances are that you’ll keep dating guys you’re not really compatible with and soon find yourself sabotaging yet another mediocre relationship.

    The problem with moving to a different location is that you can’t leave the part of you behind that caused the initial problem.

    Look into dating a guy who is in the initial stages of building something huge. You’ll probably have more to talk/fight about than you would with some dude who has already made his name.

    But you won’t do that, will you? =)

  24. Mark F.
    Mark F. says:

    P, when its the right guy you will know it…turn off the phone/blackberry in your mind while your dating…the rest will work out…you don’t need any advise (even mine!)…follow your heart…

  25. sarah
    sarah says:

    This isn’t complex. Or even about “who you are” and “time for yourself” and certainly not about “healing”. Leave those discussions to women with more self help books than sense. It’s easy. And you’ll have to trust me because I’m 22 and 3/4 and am going on 3 dates this weekend. Actually, I date more than anyone I know who isn’t paid for it. I just like first dates and get asked on lots of second, third and fourth ones. So listen and try this:

    Date guys who can’t help you. I’m in marketing for luxury fashion. I never date guys in advertising, marketing, PR, or even really cpg execs. If I date them, they will be older and I will spend tons of time asking them for advice about work, job leads, trouble shooting, and where the market’s headed. That’s not romantic.

    So I date doctors, lawyers, bankers, hedge fund guys, and architects. They’re smart, funny, sexy…whatever. Exactly what I want, need and expect from a guy. And none of them are poor. But they’re also not so rich that they can fund my bugeroning start up idea, and they’re not in my field so they can’t offer me advice(I once dated an entreprenuer…all pillow talk was business talk.). I think this will work for you too. Date doctors and scientists. You have no (work)use for them. I promise.

  26. Holly Hoffman
    Holly Hoffman says:

    I met a guy for sushi last night. He was young, attractive, owns his own business & a beachfront condo. By the end of it, I had a gig running a social media campaign for a community organization he heads. And I talked him into starting his own blog. So, I understand.

    I suppose the trick is to find guys who are turned on by a woman’s business passion, not emasculated by it. And I know they exist. A guy friend of mine told me he had no attraction to a girl who was after him for months, until he heard her chewing out one of her employees on her cell phone. They’ve been dating ever since.

  27. jenx67
    jenx67 says:

    Is your transparency for real or is it shock jockeying? Either way, I think you’re telling the truth, in which case, I need to tell you that dates grow on trees.

    Dating is a disastrous. Have you read I Kissed Dating Goodbye or Choosing God’s Best? They’re available from Amazon. Don’t you just hate it when people recommend books for how to make your life perfect? Ha!

    Have you heard the story of Rebekah? She was chosen to be Isaac’s wife by Abraham’s servant. The reason? Because she proved to be a hard worker – willing to draw water from the well for a thirsty, tired stranger. Who knows where all your hard work will lead you?

  28. Olivia
    Olivia says:

    Ambitious, successful people are naturally driven to make partnerships with people who benefit them the most. The distinction between ‘job’ and ‘personal life’ works well for people who don’t run startups in this economy– their survival probably doesn’t depend on the value they create with every interaction.

    When you’re no longer fighting for the survival of your company, you’ll have more brain power to focus on dating.

  29. Jim C.
    Jim C. says:

    This whole discussion is very creepy. There is a word for people who have sex in return for monetary gain or its equivalent (a houseful of furniture, for instance). Ugh!

  30. Missa
    Missa says:

    Penelope, as long as the primary focus of your writing is the connection between life and work, I don’t think you will be able to separate the two. I imagine that after writing hundreds of posts and having the pressure to write new posts multiple times per week, you must be constantly be analyzing your new experiences as they’re happening within the context of “life” = “career” = “translate to advice”.

    I don’t think this is a bad thing. Perhaps it’s just the curse of a writer that has built a niche personal brand that they reflect outward, while never being able to escape it inwardly.

    We see your brand as Life and Careers, but to you it’s your life viewed through a career lens (or else you’d have nothing to write about!). So you can’t escape it and please don’t try because I love reading about it and learning from you.

  31. Ben
    Ben says:

    As a man who enjoys mild aspergers, it was of a great help to me to learn there are rules and patterns to dating. Focusing on these rules helps keep that part of my mind busy, and thus happy.

    The rules are different for women and men, and they’ll sound terribly cliche, but I had to start with the basics.

    I can’t tell you what your rules will be, but I’ll share a few of mine. Note that they’re masculine in nature; I don’t know what similar rules would be for women.

    1. If a woman shares a problem, don’t try to fix it. Instead, show her she is desired or loved despite the problem. Flirt, hug, or admire in response to a woman sharing a problem.
    2. Dating is part performance, part relaxation. When initiating contact, perform a little – show off cleverness, sensuality, or humor. Once you’re together, reveal more about yourself. When you first meet, it will be mostly performance. The third date should only include perhaps 30 minutes.
    3. Interrupt cyclical thoughts and focus on the interaction between the two of you. Look for explicit signs – even if I don’t catch them instinctually and have to take a moment to interpret them, that’s still better than missing them altogether. And women seem to always be sending signs. You can even look these up online for men and women; just don’t get too paranoid about them either.

    Note that these rules aren’t about manipulating women, but being more loving, more attentive, more in the moment, yet without sacrificing my own quirks.

  32. Mariana
    Mariana says:

    Hmmmm… I think one of the reasons you are so good at working is that you’re clear on your GOALS – ie.. you know that you would like investors in your company, product placement on your radio show, knowledge about recruiting etc. NOW YOU JUST NEED TO DECIDE WHAT YOU WANT FOR YOU PERSONAL LIFE. Do you want a guy whos a good father? Wants a family? Doesn’t want a family? Do you want someone who likes to go out for a drink? or maybe someone who would prefer a hike in the mountains? Religious? Non-religious? Make a list of the qualities your looking for in a partner, and when you meet a man you’ll be focused on figuring out if your compatible, not thinking of ‘bonuses’ that might come from dating him. For instance, I want a family, so if I went on a date with a man who indicated that he didnt’ want kids, I would lose interest – I wouldn’t care if I could get a new furniture set out of him or not, because his personal goals aren’t aligned with mine.

  33. Amber Warren
    Amber Warren says:

    Penelope –

    Even fantastic bloggers might need compliments I think. I want you to know that I find your blog inspiring. I just started one and I don’t know that I will ever been as uncommonly transparent as you, but I am trying. Thank you for your honesty.


  34. Anjuan
    Anjuan says:

    I think that women who easily think of ways to do business with a man on a date come across as creative. I think that successful men would enjoy the possibility of having someone who they can date and also have as a business partner. However, that is based on the assumption that the woman and the man are in some kind of continuous relationship. If she dates a variety of men and is planning businesses with all of them, then he may feel like just another business plan.

    I find it interesting that you have been able to enter into sexual relationships with men so quickly after your divorce. Do you think that the characteristics of sex within your marriage made it easier to do so? I ask this based on the assumption that you only had sex with your husband while you were married. I also ask because I think that if my wife and I divorced, it would be very difficult for me to enter into a sexual relationship with another person. I would need quite a bit of time (probably at least a year) to recover from the failure of my marriage.

    Thanks for continuing to write though provoking entries!

  35. Reality Check
    Reality Check says:

    How can any meaningful relationship occur when one party is trying to use the other from day one?

    Yeah, that’s a good recipe for happiness.

  36. Stephen
    Stephen says:

    You need a break. I’ve found that “work” has been my greatest ally in these situations. Just dive right in there and stop “dating” for a while.

    Buy a plant.

    If it’s still alive in a year buy a dog.

    If both are still alive in another year consider dating.

    Ask that all who come into your life are for the highest and greatest good.

    That’s how I met my wife.

    Best thing ever.

  37. Jamie Varon
    Jamie Varon says:

    Why do people insist on editing Penelope’s blog for her? It gets a bit annoying after a while.

    And Penelope — I’d say that it would be incredibly difficult to separate work life from personal life. I don’t think the goal should be to separate the two, but to find a way to interconnect them that works for you! And, if a man doesn’t appreciate the way your mind works in a strategic, business-like fashion at times, then I’m guessing he’s not the one for you. ;-)

  38. Maya
    Maya says:

    P –

    you mess with my head all the time. I am reading this and thinking so many things at once – good story …bad story … it happens to her too…blah blah.

    My husband and I LOVE to talk about our work – in fact we sometimes fight to get our own stories out first …and I am ALWAYS thinking about my work ….I guess that displays passion to a certain extent and that is good.

    But you seem to be a couple of notches worse in this ladder …but I will trust that you really want to do something about it – based on the questions you asked in the end. So here you go –
    1. Your brain cannot stop – the only way to quiet it is to do something physically consuming and intense (requiring concentration) with the guy (not sex) – like skiing, video games etc. You cannot stop thinking a certain way by thinking more about it …
    2. Or do something to connect with the guy at an emotional level – like watch a chickflik – if that works …but the farmer tried to connect with you emotionally and that failed – so this will not work for you, i am sure.

    Another little mindhack (use your business mind to trick yourself ;))- think of him as your customer – your date I mean. The problem is that you seem to think of everyone as a VC. If someone is your customer/client, you ALWAYS have to think in terms of “What is in it for them? What value do I bring for THEM?” …in which case you might be able t =o use your business brain to benefit your date and eventually benefit yourself ;)

    A lot of this might sound silly – but these tricks really work for me :)
    But why do I get the feeling that you almost enjoy this problem too much to try to do anything about it ??

    I had fun commenting – I cannot refuse fun analysis such as this. Take care!

  39. Debby :)
    Debby :) says:

    I’m married, so I don’t date. However, my problem seems to be the opposite of yours. I am in sales, and I end up becoming friends with the person, especially when I’m working with non-profits or start ups. I get so excited about their ideas and causes that I forget to make money. I do too much for free or almost free. Why can’t I turn everything in a business opportunity instead of a friendship? I have enough friends!

  40. eileen
    eileen says:

    ah, you’ve found the secret to madison. it’s a great place to go to school, a great place to work, a great place to raise kids, but not a great place for single people, especially above the age of 30-ish. Especially, a business-minded, entrepreneurial, woman.

    i’ve been asked why i can’t separate my business from my life, and the culture that is my business just doesn’t separate like that, and i’m not sure it has to. and many of my friends are peers in my industry. for example, whether it’s a healthy one or not, is Google, where they cultivate a culture (for their employees) around their business.

    i’ve got no answers for you, as i’m in the same boat as you. i run my own business, i’m single and i do well financially. i’ve noticed some or all these things are a little intimidating to most of the guys i’ve dated recently.

    maybe we should collaborate about this, two heads might be better than one in this respect. the next doubles tourney, perhaps?

  41. sarahb
    sarahb says:

    i think the previous sarah’s advice was excellent and i have a few tips of my own.

    1. never tell a guy you think you have a disease until you’ve been dating for several months (unless it’s an STD he needs to know about and don’t lead with that. have that talk just before you think you are going to have sex).

    2. a couple of people have mentioned taking time off and/or clarifying what you want and the first is not a bad idea and the second is essential. you may think you are fine, but you’ve just gotten divorced and are therefore officially a basket case. seriously, even if you think you are fine–you are likely not quite as fine as you think. you admit that getting divorced was one of the worst, if not the worst, things that has happened to you. you will look back at this time and think “how the hell could i have dated anyone? i was a mess.” take stock of why you are dating and what you want. seriously consider just letting yourself process the divorce and recover. are you avoiding how you feel about the divorce? will dating someone make you feel validated?

    3. you won’t lose your social skills if you take time off from dating–you fully admit you don’t have dating skills right now anyway, but have exceptional biz/networking skills. look at the skills that translate and apply them. why do you miss men’s cues?

    4. several posters are right–who are you besides a mom and business owner? secret knitter? golfer? no time for hobbies? consider using your dating time to take up a hobby or learn a language or do something you love, particularly with friends. research shows that female friends are essential to a woman’s mental health. you rarely mention female friends in your blog. do you have any? if so, spend more time with them. if not, get some.

    5. get something to talk about besides business. you’ve done a lot of interesting research on people, how they think, behaviors, etc and you put them in a work context, but what if you just talked to someone about those topics from a different perspective? that would be interesting. i’d go on that date. you know about the world at large. talk about it. find out what your date thinks about obama, the middle east, etc.

    6. my ex and i would talk business sometimes, but we had lots of other interests, too. balance. everything in moderation. you have little to no balance in your life, which is why this is so hard.

    “wherever you go, there you are.” jon kabat-zinn

    • Bethany
      Bethany says:

      What about volunteering to coach vollyball? You’ll make contacts with all the parents, there might be single dads, and there could be investors living in Madison or people who need to hire someone and could do that through Brazen Careerist. You give back, you use your skills, you stay healthy, and you help yourself and your business.

  42. Dave
    Dave says:

    If I remember correctly, you wrote quite a bit about how wonderful life was in Madison, and why it was such a good idea as compared to NYC. Now you’re seeing that not all quality of life measurements are a matter of cost of living or other dollar based measures.

    As to your relationship issues, do you ever consider what it looks like from the viewpoint of your dates? I mean “Let’s go to bed and do you want to invest in my company?” is not a line that will captivate many men. It sounds to me like you don’t have any sort of life outside of work, but if that is the case, why fight it? If the business is so important right now, why not focus as much of your energy as possible towards it? At some point down the road, when you are ready, you’ll be able to step back and seperate yourself from that. then would be the time to start thinking about building a life away from work.

  43. Dan Erwin
    Dan Erwin says:

    As usual, you’re an absolute nut! Deeeelightful. Here’s a contrarian thought: “the authentically happy people are those who don’t distinguish between life and work.” I’ve forgotten who said that, but it must have been some important European philosopher. Ha!

    I can’t distinguish between the two–and it’s glorious. And guess what–my wife never complains about it–after 50 years of marriage.

  44. ChadH
    ChadH says:

    I discovered this blog last week, and my jaw hit the floor when I found out you actually moved to Wisconsin. I started a blog just this month chronicling my efforts to get OUT of Wisconsin. One major reason is the lack of eligible dating partners. People here get married very early and stay that way. If you aren’t lucky to meet someone young, then forget about it. Wisconsin is a breeding ground. If you’re a woman you go elsewhere to find a husband and come back to Wisconsin to nest. For years now every single girl I’ve met is in some kind of relationship, usually married. At 35, I’ve totally given up. I don’t know what it’s like for women, but it’s probably better. I know lots of single, eligible men who can’t find women. I know absolutely no women in the same position. If you’re a single man in Wisconsin, you’ve got a tough row to hoe.
    Also, as a male, this post made me cringe a bit. It reconfirms all my negative stereotypes about women, specifically that they’re only interested in money. Apparently a humble architect like myself wouldn’t stand a chance with you since I don’t run a million dollar business or make six figures. Sheesh!

    • dinae
      dinae says:

      it’s funny you say these things, i feel the same way as a woman and am planning to move out of state, as there are a lack of eligible, quality men in wisconsin/madison. i hear this over and over again from the women i meet about dating here. single women above the age of 30 have a tough row to hoe here in wisconsin as for people getting married early here, that is somewhat true, however, many of my single male friends that are my age tend to date women 10/15 (38-39yo men dating 21-29 yo women) years younger than them.

      i could go on, but i was suprised by your post, and thought you might find it interesting that there are single women your age in the same boat as you.

      relating to the money issue, the single most common issue couples fight about is money.

      P has mentioned money was a huge conflict in her marriage, and is fearful of having another relationship where financial differences are problematic. she made significantly more money than her husband did, and it was a problem.

      so, meeting someone that is close to a financial equal to her is her preference in looking for a partner. my male friends prefer to date younger women. do preferences equal stereotypes?

  45. le @ thirdontheright
    le @ thirdontheright says:

    wow a bit anxious commenting after john … what is a POS … I know what a FIG JAM is and maybe John is one of them … hmmm

    Anyways P both husband one and two and the third I have on offer (no intent to take up) I have meet at work … so what is the rush to separate work and play … common ground is a useful thing for prolonging and expanding the connection I feel.

    So my challenge to you – mix it up – make work personal .. most of the people I hire I would choose to have a personal relationship with – friend or lover – it gives me a nice feeling knowing I value them on a number of levels – not just for the sake of work and work alone.

    As always my best le

  46. sarahb
    sarahb says:

    I didn’t really address your questions in my previous post, so here’s my appendix.

    “Don’t most women spend the majority of their time with men in a work situation?” Depends on their outside interests, but probably true.

    “And don’t most women train themselves to not do dating when it’s time to do work?” Some women won’t/don’t and some do. Depends. I have dated a guy from work twice, but in general I avoid it. As for behavior, if you flirt too much, you lose credibility.

    “So how do we retrain ourselves? I am so good at figuring out how to do business with every guy I meet. How does this translate on a date?” All of the probing you do to find out how to do biz should be directed to probing about their personal life to find the personal and emotional connections between you. Not the monetary ones.

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