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. Paul
    Paul says:

    Wanna hear something crazy? I went through a bad breakup myself about 2 years ago. We’d dated for about a year (long-distance) and I was desperately in love, so I moved from Buffalo to Washington DC to be closer and to “advance” the relationship. We broke up almost the moment I got here…
    So, to combat my broken heart and be less lonely, I started going to wine tasting events, joined a running club, and even took acting lessons. Three years later, I’m a working actor in the DC area, a respected wine connoisseur, and I’ve run 4 marathons.

    Funny where life takes you when you’re not looking…

  2. Bridget
    Bridget says:

    When you have an interesting job men want to know about your work. Hopefully when you are in bed you can focus on what is happening at that moment and not be mining for connections or information. You could save the questions for the next date, it might be a good way to start out the date. Stimulating conversation is sexy. But you need to take a moment to enjoy the present. You’ll feel better.

  3. Don B.
    Don B. says:

    You are a riot. What a joy to read about you vicissitudes with regard to life, work and love/sex. Sometimes being lost in the moment occurs for many of us. Used to get my lady laughing so hard she would lost concentration and be unable to stop laughing and we would end up asleep without the sex but with a smile none the less.

  4. Diane C
    Diane C says:

    I love your posts, so real and very funny. Originally from WI and grew up there, I know what you mean..moved to CA in 97. Best move I ever made for me and my kids; more opportunity, more socializing, keeping your mind off constantly working. Maybe you wouldn’t even think of not being able to separate social and business if you were somewhere else. It’s strange what WI does to you..still have friends there caught in the same rut. You’ll figure it out.

  5. Rich
    Rich says:

    P interesting post.

    I think you need to move. You post very few complimentary things about the city you live in. I am not sure why you have to live in Madison, your compnay doesn’t seem to have a physical presence, and it if it does, sure Madison is less than optimal.

    From your stories of Silicon Valley and life in New York, I can’t imagine how you have lasted this long. As someone who has lived on both coasts and small midwestern towns, each city is not for everyone. You said that you have worked through much of the ‘dateable’ population. Surely a city like Seattle or LA will provide the lifestyle you are looking for.

    Good luck.

  6. Michael Alexander
    Michael Alexander says:

    After reading this a day late… (How come I get these after the gen y’s?) and then listening to the live voice feed I have two different comments. 1.) I agree with almost all the posts. 2.)Freeze my undies!!-is this funny or what?

  7. Alison
    Alison says:


    It’s likely you’re simply feeling a loss of control (which has great repercussions for an ENTJ) so you take control where you feel competent (businessmen). You’re trying to diagnose yourself with a label (autism spectrum) just because the categorization and organizing brings you peace.

    You’re, by necessity, living an unbalanced life at the moment. Once things get less stressful, if you balanced your intellectual/social/physical/spiritual selves you would notice a huge improvement in your ability to have a healthy relationship.

    You’re too competent at understanding relationships to be on the spectrum. Once you can take time to feed your introverted intuition rather than needing to bulldoze for your business with your strong extraverted thinking you will be fine, I promise.

  8. curiously random
    curiously random says:

    Penelope, let’s swap. I’m on the west coast looking for single women and you’re in the midwest looking for single men. According to that map, I’d be better off in Chicago than in San Francisco and you’d be better in SF or Seattle (both beautiful cities btw).

    Post-divorce life takes about a year to normalize. Give it time, don’t force it, and don’t feel bad about not feeling good all the time. Have ice cream for lunch. Really, it does wonders once in a while.

  9. CAK
    CAK says:

    Penelope, your greatest strength and your greatest weakness is that your are an opportunist. But I think an opportunist lives a hard life–always hyperalert for the opportunity around the corner OR scrambling to create an opportunity. And yes, as others have said, your datee may feel used.

    You are not clear about whether you are lonely, in need of an in-depth relationship; or simply needing to scratch an itch (sex). When you said that you fell asleep in the guy’s arms . . . that seemed to be the tenderest and most authentic moment (to me).

    I have no inspiration or advice–except that I agree with the responses that say you should relax and stop trying so hard. Seems to me, opportunities come when you are NOT trying so hard to create them/take control. Like when you want to have a baby and cannot get pregnant, but as soon as you stop trying and stop stressing about it, it happens. Just a little lesson to demonstrate how we simply cannot be in-control, no matter how hard or how smart we work at it.

    If the above strategy is any good at all, you will meet someone around a common interest, in a relaxed setting where “the first date” is hardly recognizable as such.

    Chris from Wisconsin

  10. Michael Alexander
    Michael Alexander says:

    Life is about creating. Creating sensuality and extended periods of intamicy is another story for those of us who are creative or have minds that are not wired for the normal relationship. Saving oneself for the right person has merit in that it’s a psychological gamble to troll about to get ones ashes hauled.(let’s do a blog on phraseology). Sex and intimacy create a bond for most of us that can be tied to accumulated error that leaves us wondering if after 40 or umff 50 if it is just easier to go it alone. Now the fun can really begin. We can start creating again without the hassle of chasing intimacy and sensuality to the far corners of genetic frenzy. Not so fast buster! I can say in a Wisconsin minute that before we head down the devils drainpipe we must all have fun !
    If P is not having fun in Wisconsin it’s cause she’s hanging with the wrong blocks of cheese. Buck up there P!

  11. Phil
    Phil says:

    Talk about outing yourself as a gold digger…PT, you only seem to care about money, power, and prestige. I pity you, because there is so much more to life. I’m glad you did finally wise up and realize that your career advice was about as professional as a little league baseball team and gave up on it. At least now you can just “dish” about your life and not attempt to make it into something it is not. It sounds like karma is starting to catch up…

  12. ogog
    ogog says:

    gogo boys will make you happy, if all that you wanna is sex. You know, just do like the men, use hookers.
    If you want something more, choose someone who you can’t do business, like your boss.

  13. Pirate Jo
    Pirate Jo says:

    Penelope, why do you feel like you need to be dating in the first place? If your work life is really what you want to focus on, then just do it. You also have at least one child that I know of – maybe you could also find some time in there for your kids and give the parade of men a break for a while.

  14. Belinda
    Belinda says:

    Getting a new dining room set for a radio plug isn’t a business transaction–it’s using someone. You need to learn the difference between a transaction between two corporate entities and favors between friends. If you have any friends.

    Please stop thinking about what’s in it for Penelope.

    • Dan
      Dan says:

      But that’s what she does, work the angles. What you call “using”, she might call “networking”. I don’t recall that she ever claimed to be a saint.

  15. W. Serafin
    W. Serafin says:

    Ugh Penelope…I feel your pain. As a former Milwaukee/Madison girl, the dating is weak, especially in Madison. East side of Milwaukee might be better for you, but nothing does compare to what you are probably used to. I wish I had more words of advice except take a few trips to Chicago?

    Was it a Steinhafel? They do own everything…

  16. Dale
    Dale says:

    Do you know who you are or what you really want? That’s what you’re really asking in this post.
    It isn’t so strange, I don’t know the answer for myself nor for you, and neither do most people.
    But what you’re asking is probably best answered by deep soul searching (done alone which you hate to be), or by a great shrink, or by loved ones who know you best – from childhood. Seek answers there.
    Other than that let life happen, it will anyway:)

  17. Chris Bauman
    Chris Bauman says:

    Because work takes up so much of your day, I have to agree that it is sometimes hard not to talk about it on a date….whether it is to try and impress, you are letting off steam or to find it to be an easy topic of conversation. Unfortunately this is all surface material. You really find out who someone is after say the 4th or 5th date I think.

  18. deepali
    deepali says:

    I think the problem is very clear – your brain/mind/body/soul doesn’t want to focus on dating right now. It wants to focus on work. Why fight it? Throw yourself into work, and get yourself a vibrator. To each in its own time.

  19. editormum
    editormum says:

    What I notice is your value judgements. First thing you say about the real estate guy is that he is a bit chunky around the middle — that says that the first thing you noticed and evaluated was his physical attractiveness / fitness. Then you call him a “mogul,” which has definite connotations of Money. Then you talk about the furniture guy, and you are assuming that he is not rich or even well-off, and that he will dump you and take you for every penny he can get.

    Maybe you need to do a little less fantasizing, and a little less pre-judging, and get grounded in reality. How do you know that the furniture guy is the kind of guy who would (a) give you a room full of furniture for sex, (b) not be a good financial provider, and (c) divorce you and then demand spousal support? How do you know that the “mogul” really is rich?

    Go on a date and do something that is totally unrelated to business. And stop obsessing about sex. If you need the release, there’s ways to get that without complicating your male-female friendships until you’ve known the guy for more than a few days.

  20. me
    me says:

    I dunno if it’s you. I spend a lot of time in a counseling and the biggest thing everyone seems to need to learn there is to accept themselves the way they are. I mean, always strive to be better, yadda yadda yadda, but how you feel inside, your intuition… you know what? It’s ok.

    Lots of people who commented here seem to have advice on how you should be but I think anyone in your boat might end up feeling the way you do. But yeah, if you had more men to pick from that would help. People are always saying to connect with those likeminded, say if you LOVE scrabble, join a scrabble group and find someone as intense about it as you. Maybe the right guy will be one who is equally ambitious.

    Your divorce wasn’t that long ago – this is just a transitory time. But I love when you write about your love life because it helps me deal with my own, which is rocky and tremulous and not such a great place to be. Your bravery helps me with my own fear, so thanks for your candidness.

  21. Cheryl Allin
    Cheryl Allin says:

    I just found your blog and I think I’m in love (not in a creepy stalker way). Great post and I’m the exact same way with my husband. I can always tell I’m ‘doing it again’ when his eyes glaze over at more talk of twitter, rss feeds, community. It took me years, but I don’t apologize for having passion anymore. I’m a wacky left-handed gemini and if I wasn’t, I’d be boring. Maybe I’m boring to others, but I like me – and that’s paramount. As long as you’re not afraid to put yourself out there, you have no worries. Eventually, the stars will align and you’ll stumble upon someone perfect for you…or at least perfect for you right now. There’s nothing wrong with you, you stay comfortable in your own skin and that will resonate with people you meet. You’re 100% unique, smart, interesting, skilled and people will be drawn to you.

  22. lori nelson
    lori nelson says:

    Call me romantic or post-feminist, but put I think a woman needs to be able to relax and put the burdens down when she is dating, especially if she wants to hook up with a man with any quality at all. Judging from your posts since the divorce, you want to have a great connection with someone substantial who you can trust and respect, and a relationship that is deeply and irrationally erotic. A guy like the one you want is going to be bored by a money pitch or work talk; he won’t connect with you the way you want him to connect with you.

  23. jemimah ruhala
    jemimah ruhala says:

    Have you considered the advantages of online dating? You have longer to decide what to say, so the conversations will not automatically go to business. You are not tied to your location so the dating pool is bigger and much more diverse but you don’t have to relocate until you know it’s worth while. You get to know a person’s mind without the social awkwardness of dating a stranger. You can get to know people you would normally write off too quickly in real life situations.

  24. Maggie
    Maggie says:

    I have to say I’m kind of scratching my head over this post. Are you looking to date for the sake of having fun and sex? Or are you interviewing candidates to be your next husband? Or to be your next investor? They seem all mixed up to me–like you think you’re looking for something romantic/sexual but in reality you’re looking for funding.

    In any of these cases, I really don’t think moving somewhere where there are more single men is going to make any difference–after all, it’s not the quality/quantity of men you’re meeting that is causing your inability to turn your business mind off. It’s you.

    Maybe it’s because I am not a business person that dating/relationships/sex have never been problems for me. I am as into my career as the next person and have a hard time turning it off in my head, but I was never looking for guys who could further my career when I was dating–I was looking for guys I was attracted to and wanted to date.

    I’m not saying this next thing facitiously and I know everyone reading this will be horrified, but maybe you should consider dating guys who are not single. I don’t mean going around plucking guys from their happy married lives and stealing them; I mean there are many, MANY guys out there who are married only for appearances or finances and whose wives could care less what they’re doing because they’re doing the same. It would keep you from having to worry about all the what-ifs as far as you having to support them if you ever got divorced. I don’t know that it would solve the whole not being able to think about anything but business in bed thing, but who knows–maybe with the possible marriage pressure off the table you’d be able to just relax and enjoy instead of trying to close a business deal.

    As to the work/dating question–I met my husband at work. We talked about work some–ok, a lot–but when it was time for fun or sex, thinking about work didn’t occur to me. Maybe the problem is that the guys you’re dating are no good in bed; if they were, your mind wouldn’t be wandering.

  25. CAK
    CAK says:

    Maggie said some wise things:
    It is you–you cannot escape this problem by morning to another place with more/better opportunities.
    YOU, Penelope, have a mind that never turns off–you are thinking about an opportunity for funding; and/or an opportunity for a hot topics to write about. And maybe other things, too, like your kids’ nanny, school, general well-being.
    The Zen masters would advise that you find a way to turn off your racing mind. They would probably want you to learn to meditate . . . This is much more of a skill than just “relaxing”. And you would need to learn to “let go” in the Zen way of “detachment”. Do you think you could ever adopt the position of taking OR leaving some goal you had set for yourself (that high level of detachment)?
    They say, about ADHD, that it is not so much an attention deficit that kids have, but rather a hyperfocus, such that they cannot break away to refocus on the next thing. That those ADHD kids are not able to let go of the last thing, and transition smoothly to the next thing . . . and then move on again to the next thing . . .

    Chris in WI

  26. Grace
    Grace says:

    Your dating is just another thing to accomplish on your “to-do” list. Does it really feel good, or does it feel good because you like crossing things off the list?

    You’ve been with men in your industry, you’ve been with men outside your industry. It’s not about the men, or lack of them. C’mon, you know this. Don’t hide behind your own comfortable quirky neediness. What is the payback that you have been receiving for it? Is it really that great?

    Desperation just attracts desperation. There are some things that shouldn’t be squeezed in or forced. Trust that God has something in store for you and just wait for it for a while. Be up for the challenge of standing on your own, trusting that you already have all that you need.

    Have you read, “Eat, Pray, Love”, or is that just too obvious. Watch “Groundhog Day”. Very spiritual.

    All the best.

  27. Grace
    Grace says:

    And, all this alone time isn’t a means to the end known as “finding a good catch”. Just enjoy it for what it is. Time alone.

  28. finance girl
    finance girl says:

    I’m not sure I see something that needs ‘fixing’ like you do or some other readers, I think you are just very passionate about what you do and thus you get interested when someone else you meet, regardless of if it’s a potential date or not, is doing something you are interested in.

    I think if one shows true interest in another, that’s the key, but if one is just in it to see what they can get out of it (shameless networking, for example) then that’s a huge turnoff.

    Not saying you are doing that, just thinking of my own experience with some ‘friends’ who turned our friendship just into a ‘hey how are you hey can you do this for me’


  29. matt
    matt says:


    that’s hilarious. in a sad way. but still hilarious. i own a MRI franchise. (recruiting franchise) i am constantly thinking about who goes where, who knows who. it’s manic.

    i met a woman at a restaurant and she was a dental hygenist (sp) (great teeth!) but of course i thought, she belongs in sales. so we talked about it, instantly turning what was amazing chemistry into a transaction. she probably thought to herself, omg a headhunter! i can get into sales now… and i’ve lost.

    that happens to me a lot.

    do you think your openeness about your personal life affects your funding and corporate life?


    ps can u send any of your brunette athletic spanish or italian friends in NC or NYC my way? u r a recruiter right!

  30. Charles Xavier
    Charles Xavier says:

    Love your column, Penelope
    Although I love your column, I have not read it enough to realize that you are now divorced from the husband you mention in previous columns. Sorry about that. Anyway, I want to tell everyone to be critical when looking at statistics of where the single people are. For example, I live in a city that, according to the Census, has a lot more single women than men. This is very true…but the median age of these single women is about 20 years higher than the median age of single men here. I’m lucky because I don’t mind dating older women, but not all middle-aged women want to date a 26-year-old. And…let’s not discuss the comments my 20something male cohorts have about “this town being overrun with cougars.” So research deeper when you see these singles statistics.

  31. Alora
    Alora says:

    I had to go to a lot of effort to find dating circles that were so totally removed from work that I wasn’t tempted to co-mingle the two. It took ages to figure it out. It eventually worked, but now I have a different problem: because I have a husband who is not in my field and who is not a workaholic (like me), we struggle over things that I never expected to struggle over.

    Pick your battles. No matter which ones you win, there will be plenty of others waiting in the wings to kick your ass.

  32. Dana Boyle
    Dana Boyle says:

    P –
    For what it’s worth:

    You haven’t asked yourself what you want out of a relationship or in a man/mate. Instead, you’re focused on business.

    Take some time to make yourself a list of what you want in a mate. Examine yourself. Be honest. Be very specific. Don’t dwell on what you don’t want, because what you focus on gets bigger. If you find yourself saying, “I don’t want another man who quits his job and then I have to support him,” then turn it around to something you do want.

    Keep dating as you do this. Expand your list as you date. You’ll find that you attract the men who are like the list, and you’ll realize you forgot to add this or that. Eventually, the right guy will come along that matches your order, and you will know it when you meet him.

    Give it a try. You can always go back and “network” with the guys who don’t fill your order.

  33. Indrani
    Indrani says:

    You know, just today, I was thinking long and hard about this. I know it’s not healthy but I barely have any life outside of work. What time I have out of work, I spend alone because I want to. I mean I need SOME time when I can read, surf, cook, think and sleep. Can’t all the time be around people.

    I am still at the stage where I am trying to not date at work. But I can see myself there with you too. That will happen soon. Being a huge introvert, hasn’t really helped me network. Need to work on that.

    Thank you so much for the good work that you are doing. I read your articles quite regularly and find many gems of good advice.

    Warm regards,


  34. Daniel
    Daniel 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.

  35. Bill Bryce
    Bill Bryce says:

    This all work, no play lifestyle that appears to be upon us these days is taking it’s toll on family life of that there is no doubt. The worldwide recession will only add to this. Proper family values are gone and will never be the same sadly.

  36. Jamie
    Jamie says:

    Your story sounds exactly like mine. After my divorce, I wanted to date, but I felt I had very few options because I simply didn’t know any single men. After about a year, I realized that the problem was that I needed a new group of friends. Most of my old friends were married and the social circles I circulated in weren’t conducive to meeting single men.


  37. Alfred
    Alfred says:

    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 totally agree with this definition of lawyer.

  38. Herpes
    Herpes says:

    Very interesting insights on work and dating. It seems that work and relationship both require some professionalism ( I mean dedication)!

  39. Jason
    Jason says:

    It is important to focus on work and be successful, but you can’t let it define you as a person. I am annoyed when all people want to talk about is work. Of course that is a major part of their life, but you have to have a social life and get joy from something outside work. Even if its not a social life, at least some good hobbies that you can talk about and stay interesting.

    • Google
      Google says:

      Does not matter what people is talking about: a pedofile may talk about his postage stamps collection hobby and it would not define him as a person

  40. Sports Flooring
    Sports Flooring says:

    informative entry not just for the ladies I suppose.
    It is hard to find the right balance between personal and work and unfortunately for many of us it is the work that we do that defines who we are as people and that is hard to switch off.

    What makes a successful marriage…when you find out do let me know

  41. Ipod touch microphone
    Ipod touch microphone says:

    “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.”

    unwittingly, One of global warming causes is Divorce, we spend electricity twice after that, LoL.

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