How to go to a meeting when you want to sit home and cry

,

Here’s what last week was like: On Sunday I flew to Detroit and gave a speech at the Public Relations Society of America. Then I flew back to Madison on Tuesday and met with an investor who only wanted to talk about my blog even though I want him to put more money into my company. Then the farmer slept over Tuesday night, and drove me to the airport at 4 a.m. so I could fly to Ft. Lauderdale to give a talk the Electronic Recruiting Exchange. On Thursday morning I woke up at 4 a.m. again and flew to San Francisco and took a car to Sand Hill Road, venture capital mecca of the universe.

In the car, I called the farmer for fifteen minutes of fun. I should have been preparing for the venture capital meeting. But I was so tired, and I told myself the call would make me perky for presentation edits.

In that car, on that call, the farmer dumped me.

He has actually dumped me a lot. Five times in four-and-a-half months. In fact, he’s dumped me so often that he has already dumped me once when I’ve been on the phone in a car. And he has already dumped me once when I flew to San Francisco.

So you’d think that maybe this would be familiar and I would just plow through it like the other times. But there is a theme to the dumping. He wants something to be different and instead of telling me, he dumps me. So I convince him that if he asks for something then probably I can give it to him, but he has to ask. So he asks and we go on a few more weeks, and then he dumps me again.

This time, I realized that I should not keep convincing him to ask for something instead of dumping me. I think I realized this after I twittered that he keeps dumping me and it was like confessional because I hadn’t told anyone before, and the universal tweet response was that I should get out of the relationship.

So this time, when he dumped me, I decided it was really the end.

I said, Okay, and we hung up. Nothing else. You might think that being together four months would mean we have stuff at each others’ houses. But the farmer is 38 years old, and he’s never been in a relationship longer than four months, so I think we both knew that leaving anything at anyone’s house was too optimistic.

Which means it’s a clean, no-strings break.

Which would have been completely true if it weren’t that I was so sad. And if it weren’t that I had to give a big presentation two hours later. And on top of that, I didn’t have the sales numbers finished that I would need for the meeting.

So I took drastic measures. I could tell I was in shock and I was going to need to cry and I didn’t have anywhere to break down. So I got a hotel room, even though I wouldn’t be sleeping over. I sat on the bed and stared at the wall and got scared that I would never be in love again in my life.

Then I worried that I would not be able to hold my life together. I have too much with the kids, and the divorce and the company and now being dumped. It’s too much.

But then I realized that I never fall apart. I get through lots of stuff and people always say it’s so much but really, what else can you do? People get through what they have to. So then I worried that I’d get through this but I’d be numb. One of those people who is great at work but checked out everywhere else in life. I worried that I wasn’t crying.

I didn’t cry. I opened my computer and realized that I didn’t even have the numbers I needed for making a slide. So I called Tim, the guy who helps me with my PowerPoint stuff. And I said, “Where are the sales figures?”

And he said, “Where is the email you said you’d send so I could do the sales figures?”

And I said, “Crap.”

So we worked on the slides, and I know my voice sounded like I was trying really hard to hold it together, but I hoped that Tim thought it was because I was nervous that I was missing the slides.

I said, “I hope the guy at [renowned VC firm] is nice.”

Tim said, “You don’t need someone to be nice. You need someone to be direct and honest.”

And then I started crying. I said, “Tim, the farmer dumped me.”

And Tim said, “Again? He dumped you last time you were out here, too.”

“This time I’m not trying to convince him,” I said. “And I do need someone who is nice. I’m sick of direct and honest. I want nice.”

Tim said, “I’m sorry.” He suggested that maybe I should move the slide about my accomplishments to the front of the presentation so I can feel good about myself right away.

So I redid my makeup to fix the teary mascara. And I put the slide in the beginning of the deck, and I went to the meeting.

I ate three chocolates in the lobby because I remember reading that kids who ate a chocolate bar right before the SAT scored higher.

I pitched the company. The guy said he was familiar with my site.

“You mean you read my blog?”

“Yes,” he said.

I told him that my company is not my blog. Then we ran through all the company stuff.

At the end of the presentation, this is what he asked me: “Who was your childhood hero?”

My first thought was that this was like a classic interview question: “What food would you be if you were a food?” And I decided that it was important to give an answer that I could talk about in a way that would be consistent with who I am. And who I want him to think I am.

I said, “Judy Blume.” As soon as that came out of my mouth I realize that I was going to have to talk about myself as a writer, and not as a CEO. And all investors want to grill me on my ability to lead a large company. Except the investors who immediately think their friend will run my company because I will be a blogger.

It’s times like this, paragraphs like that, when I think, what am I doing? How am I ever going to get funding when I write so often and openly about my dark, funding underbelly? I used to tell myself that the investors have no time to read my blog, but in fact, the investors are so enthralled with reading my blog that they have started asking for advice on starting their own blog.

And still, I keep writing. Because when I think about how I got though last week—the too-much travel, and the high-pressure meetings, and being dumped for the fifth time—the only thing I can think of that will make things better is to write about it. All of it.

And then I think that the investor is a genius for asking me my childhood hero because it does, in fact, reveal who I am. I just have to keep reminding myself that Judy Blume is not only a writer. She is an empire.

115 replies
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  1. Amy
    Amy says:

    Judy Blume is an empire. I am a librarian (so I know).

    You certainly are an empire. Penelope, I think you are extremely well branded!

    Farms smell :)

  2. Frank
    Frank says:

    My take is that you are abusive—without meaning to be or even realizing it—but abusive nonetheless, to the men in your life. As an example, no man wants to see private details about his life thrown up on the Internet, even if done semi-anonymously. You obviously have some bizarre need to indulge yourself this way, but maybe you should think twice about being so overbearing. Anyway, I hope things work out better for you in the future.

    As for your company, best of luck there, too. It’s unfortunate timing to be seeking VC funds as the economy tanks. Maybe you really don’t need their money. GeekMBA360 makes some sense above.

  3. Yu Ming Lui
    Yu Ming Lui says:

    I never knew chocolate could boost confidence – great tip.

    I agree with Editormom – the farmer is emotionally immature to dump you every time he can’t get what he wants from you. How infuriating that he could be so insensitive and selfish. It just shows he just thinks of himself, and not you.

    Penelope: You did great of holding yourself up during the meeting. Judy Blume is a great heroine for all women. Cheers.

  4. Lindsay Price
    Lindsay Price says:

    Honesty and Transparency – aren’t those the big buzz words for blogging these days? I’m not sure I’ve read a post where I felt the picture of a human being so completely and vividly. Granted, I can understand your frustration over wanting to be seen as a CEO and being taken for just a blogger – but you are a writer. You have a gift.

    And there aint nothing wrong with a good cry.

  5. Liz
    Liz says:

    “My take is that you are abusive – without meaning to be or even realizing it – but abusive nonetheless, to the men in your life. As an example, no man wants to see private details about his life thrown up on the Internet, even if done semi-anonymously.”

    The commenter above, Frank, went on to chastise P for being “overbearing,” too. I agree that not everyone wants to be written about, and not everyone wants to date a workaholic. However, was P supposed to say, “Hey, I should definitely try to become someone in the relationship that this guy would like better in order to not trouble him?” Because the word for that is “Door mat.”

    Frank is showing a pretty basic misunderstanding of human relationships. It’s not “abusive” to fail to anticipate that someone won’t like a certain behavior. It’s only abusive if, in the face of protest and evidence of pain, someone continues the disruptive behavior. P’s behavior was not obviously disrespectful toward the man. She didn’t hit him or do things to deliberately inflict pain. She was herself. That’s VERY different than abuse.

    Rather than actively hurting her partner, though, Frank seems concerned that P did not ANTICIPATE Farmer’s preferences. That’s not abusive. That’s assuming the Farmer is a grownup with the ability to state his own preferences when required. (All evidence to the contrary).

    I’m not sure why Frank wants so badly to label, “A woman I would prefer not to date,” as “Someone who is treating men badly.” But failing to live up to some feminine standard isn’t abuse, Frank.

  6. Patrick
    Patrick says:

    I’m sorry about the farmer. I am reluctant to overgeneralize, or blame this on him, but here is my two cents…

    Until recently I also lived in Wisconsin. And had done so for several years. And I met and dated several nice guys. (I was a guy dating other guys, but I don’t think that makes a difference here.)

    They were all great, smart, handsome, well-rounded human beings. And there’s the “Minnesota nice” or “Wisconsin nice” syndrome, if you will.

    But the flip side of that consistency is that I found many of the guys to be uncommunicative when it came to problems, or issues, or personal feelings.

    I think it’s a combination of that “niceness” and a “git ‘r done” mentality that these guys had a hard time discussing issues or being emotional. I don’t think they were cold or unfeeling, but I liked to think of it as “emotionally frugal.”

    Avoiding the lows and enjoying the consistency of the middle ground is great in a relationship, but not at the expense of knowing what the other party is really feeling.

  7. Angie
    Angie says:

    P, there is a great ebook on the internet called
    Dating without Drama. It’s really helped me out and changed my outlook on dating. Download it and give it a read.

    Don’t ever sell yourself short. Make yourself happy and love will come. Don’t compromise!!

    angie

  8. chris keller
    chris keller says:

    PT, you are like a good critical care/intensive care nurse, in that, when the situation is changing rapidly, you can quickly shift gears, wheel around, anticipate (new) needs and FUNCTION.

    You are also like the football squad members, on the run, quickly looking over your shoulder, putting up your arms, even if you are off-balance, to catch the pass, and run for the yardage–if not for the TD. You have an injury? Sure. But you soldier-on.

    I am guessing you don’t want to hear anything mean-spirited about the farmer. You hold him dear, probably, even now, after the serial dumping.

    I once got dumped by a guy I held dear. He wasn’t a great communicator about emotional thing/relationship things, but he did say “It is not YOU. It is ME.” That was his whole explanation. I had much to think about over time, trying to interpret that short explanation . . . He came back into the family a year later. And he was killed a year after that. Loss has many faces and many meanings . . .

    I am now with a guy who quietly supports my rabbitiness and mood-swings. He knows I have good judgment, am changeable, can turn on a dime. He accepts that I am tense and intense. He is benefitting from my creativity and my good ideas, and my rapid analysis skills. He KNOWS that I HAVE to push and push-back . . . I keep the drama up and going, and he seems to be able to live with that. I KNOW I am not easy to live with . . . I appreciate him, his calm and stability. It is a good foil for me. He lets me be myself. It is not too exciting, but it is
    good–it is Zen-mellow. I need that.

    Judy Blume: So we return to your investment in writing. Methings thou dost protest too much (in another post, recently) about NOT needing to write a book. You need to write SOMETHING, if not a book. Is your blog enough for you? Write-on, PT!
    Your new blog or your new book should have the term “resilience” in it, don’t you think?
    CAK

  9. Mark W.
    Mark W. says:

    I’m surprised nobody has mentioned one of Penelope’s recent Twitter feeds dated 10/24/08 – “I made a deal that the farmer can see my posts before they run. He says trying to control what I write is like holding water in his hand.” – http://twitter.com/penelopetrunk/statuses/973717937
    You don’t have to read between the lines as the word control is there in the feed. However we don’t know if he actually used the word control. I don’t know how you could ever expect to control Penelope’s writings or any writer for that matter. I read this 140 character or less feed as an element of mistrust between Penelope and the farmer. This Twitter said something much more about the relationship rather than the individuals.

  10. Lara Kretler
    Lara Kretler says:

    Penelope, wonderful post and so beautifully open of you to share your pain, sorrow and struggles with us. I always wonder how I can show my true self yet still be professional in my blog, and you’ve certainly shown us the way. Cheers to you. Clearly he was NOT deserving of you!

  11. Juki Schor
    Juki Schor says:

    I am still struggling to understand the American blog world. If this is true and real, the dumping I mean, I am sorry, I hope this is not the general “American way” to do it…I am amazed that you write so openly about your personal relationship struggles and kind of wrap it into career advice, but of course, I have always wondered how people can perform “on stage” when something awful happened to them shortly before the “performance”. I guess that is called professional. The whole post leaves me still with the impression that life is very “dynamic” at your end of the world and I would probably feel like going insane with managing it all. Good you don’t, seems that you have the “7 lives of a cat” in your backpack :-).

  12. Jordan
    Jordan says:

    How awesome are you to have the guts to express yourself and tell thousands of readers how you feel and still remain professional.

    Some individuals don’t express themselves when they should with people they’ve known for years!

    Then you pull off a presentation after your ordeal. Keep on kickin’ butt cause you’re the real deal sister.

    Take care of yourself and if farmer guy calls, don’t even pick up the phone. He had a gift and passed it up. Keep on expressing yourself-just not to him. He seems like someone who passes up opportunities a lot. You clearly are not that way.

    Anyhow Judy Blume is wonderful. Any chick that has banned books under her belt is okay with me. Here’s to empires and fearless expression.

  13. Grace
    Grace says:

    We are all drawn to Penelope because she bares all on her blog. And, you may recall, this is what drew the farmer to her. If the break-up is in part due to her revealing posts, then the farmer was a fool, for he should have known what he was getting into. Based on the posts, the farmer seemed like a fine man, but not the right man.

    Penelope was dumped for being her direct, imperfect self. Penelope, wait for someone who “gets” you. Better yet, don’t get involved with a guy until you “get” yourself. Another suggestion – seek friendship with other strong women who feel as together/messed up as you do.

  14. Leanne
    Leanne says:

    I was at the ERE conference for Penelope’s talk on Wednesday…without a doubt the best session of the conference. She even took the time to help boost my self confidence.

    I wish I could do the same for her right now.

  15. Jill
    Jill says:

    I’m a Wisconsin-born woman who dated “Wisconsin nice” men and I agree with Patrick that they don’t do well with communication about issues or personal feelings.

    My fiance dumped me by phone just before my finals my first year in business school. So I feel for you! Turned out to be the best thing that could have happened to me. I learned that I could try at something, miserably fail and still survive and thrive. And I found out that I needed a different kind of partner in my life, which I have now. He came from California, if you’re wondering where to look for one! :)

    You’ll be OK. But I agree that you should take the time to grieve a tough year of loss.

  16. Lane
    Lane says:

    Thanks for the edit list of helps for going into that meeting even when you are experiencing loss. That should be added to the original post.

    Because we’ve all been there.

    @Jill: Ditto on the “Wisconsin nice”. That also goes for “Illinois cool”.

  17. Harry Joiner
    Harry Joiner says:

    I’d have to say, as a writer, that the final two lines of this post are the smartest two closing lines of any blog post I have ever read. Effing brilliant! It’s as if you’re saying to the VC-lurkers “Here I am. Take me, warts and all, ‘cuz that’s where the money is.”

    But careful. The obvious follow up questions any self-respecting VC-lurker will have are “What business is Judy Blume in?” and “What business are you trying to establish?”

    Is it publishing? Fine if it is, but is publishing a business that your VCs understand and can add value to you as a partner? It took Judy Blume decades to become “an empire.” My first hand experience with VCs is that none of them can wait that long.

    Your fan,
    Harry

    PS – “… the universal tweet response was that I should get out of the relationship.” You’re getting your relationship advice from a liberal internet mob? Sounds like a great way to drive your life into bigger ditch than it may already be in. Call me anytime. You have my number.

  18. Kate
    Kate says:

    Love your blog, have read every one and can really relate in many ways. I didn’t meet my husband until I was 30 and thought I would be single forever. Then I met him and I learnt the secret, which I will now share.

    Good relationships are easy.

    The right guy will say, do whatever you need to and I will always be there for you. They will be so nice to you all the time that you just want to be nice right back.

    Don’t persevere if it’s tough, get out. Pain is not a sign of love.

    We have all been there, tyring to juggle it all. Just wanted you to know that there are guys out there who will ring you two hours before a big meeting to say they love you no matter what.
    That’s what you deserve, hang in there.

  19. Matthew
    Matthew says:

    This is only my second comment in approximately three years of reading your blog, but I thought this might be an appropriate moment to let you know how much I admire you and enjoy reading your blog. Thanks for sharing your life and hard-earned wisdom with us.

  20. Rachel
    Rachel says:

    Thanks god the farmer is gone! I’ve been holding back, since he keeps lurking, but I hope he is gone for good (if not, you will have a hard time admitting it to all of us!) If you stayed with him, he would just do this again, before another important meeting. If you married him, he’d be calling up asking for a divorce before important meetings. Ugh. I always thought he was just a rebound relationship, anyway.

    I am sure you will be able to hold your life together. Hire some more people to help you! (Alternately, fly your best friends in to cheer you up!)

    Thanks for the reply to Karen about how to get through the meeting, which you seem to have forgotten about in your post.

    But you glossed over what Karen suggested in her post, which I want to second: Don’t be frustrated that they want advice on starting blogs–charge them! Not only can you make money doing this, and expand your personal brand, but you can get to know key people by working closely with them on something they care about.

  21. Katherine
    Katherine says:

    I was feeling sad, like I was going to burst into tears, because I left my job without one to go to a little while ago and it was getting to me. It is getting to me.

    I thought that maybe if I read your blog it would remind me that I left my job for the right reasons, that the “rules” of career change are out-moded and that I should be congratulating myself for forcing the change that I need in my life.

    Then I read your story about being dumped. He dumped you, I dumped my job… I feel like having my career up in the air is the defining facet of my identity right now, while you were feeling the opposite. It made me feel better to realize that I have a lovely relationship to be thankful (and not teary) for. So maybe it’ll make you feel better to know that there are others out there who are struggling, aching, yearning to find work that fits them, that means something to them and that doesn’t make them cry. You have that and it’s a beautiful, meaningful, ever-changing thing.

    And today you helped me.

  22. spleeness
    spleeness says:

    I wanted to pour my heart back out to you here because your words really touched me. I don’t know if you know how much your honesty means. I spent last night pouring my heart out in my own blog and was simultaneously scared and compelled to do so and this morning, I feel comforted by your own confessions because it helps me feel that somehow I am not alone.

    I too worry about all the same things you mentioned. I am so sorry for your loss of the relationship. The timing is terrible, there are no words to express all you must be feeling inside. Keep writing, it’s beautiful. Big hugs…

  23. spleeness
    spleeness says:

    One more thing. I’m reading other people’s comments. Someone wrote: “seek friendship with other strong women who feel as together/messed up as you do.”

    To this I’d like to requote (sorry, I don’t know the original source): “The only people who are normal are the ones you don’t know.”

    Everyone feels a mess inside at some point or other. The stronger ones can talk about it.

    Keep talking, Penelope. Your strength, courage and vulnerability moves us all.

  24. Regina
    Regina says:

    Lyrics from an old song captures this exactly:

    There’s no business like show business like no business I know
    Everything about it is appealing, everything that traffic will allow
    Nowhere could you get that happy feeling when you are stealing that extra bow

    There’s no people like show people, they smile when they are low
    You get word before the show has started that your favorite uncle died at dawn
    Top of that, your pa and ma have parted, you’re broken-hearted, but you go on

    There’s no business like show business and I tell you it’s so
    Yesterday they told you you would not go far, that night you open and there you are
    Next day on your dressing room they’ve hung a star, let’s go on with the show!!

  25. Jennifer
    Jennifer says:

    Your previous posts about you and the farmer always bothered me a bit. The words that you used to describe some of your experiences made it sound like he was always trying to teach you something or mold you in some way. It doesn’t surprise me, then, that he’s not good at long term relationships.

    Contrary to popular belief, if you have to work so hard to make a relationship work, maybe it’s not going to work.

    Good relationships should not be hard, you shouldn’t have to “make it work” with someone to be successful, and you certainly shouldn’t feel like you need to live up to someone else’s image of what you should be.

    On balance, being with your partner should give you energy and make you feel good about yourself. If that ain’t happenin’ (especially 4 months into it), move on and know you did it as a sign of self-love.

  26. JB
    JB says:

    “I’m sick of direct and honest. I want nice.”

    Like a lot of women, you want to be lied to. Good luck with that.

  27. Leslie
    Leslie says:

    Penelope

    The farmer just gave you the space you need to make room for someone new in your life.

    I was dumped like that about 18 years ago by phone in a humiliating way – but I am grateful. A week later I went on a fun date with a fantastic man who I have now been married to for 16 years.

  28. Gary
    Gary says:

    I “discovered” PT when I attended the PRSA conference in Detroit. She was the highlight of an otherwise worthless conference. Her personal brand is awesome and its value immeasurable. Some VC will realize that soon.

  29. Leroy Jethro
    Leroy Jethro says:

    Time to get serious about making things work with the farmer. Put your other items on the back burner to be either brought back later or thrown out.

  30. Connie Mettler
    Connie Mettler says:

    Go, Penelope!! Mighty gutsy to share all this not only with us, your intimates, but with the investors (yikes!). Would Hillary have done this? how about Sarah?

    Who cares about the guy…plenty of fish in that ocean. I know, at 66, still plenty of men in my life. And, as a mother, think the guy isn’t nearly as important as the kids and the earning money parts, and, as you are in Madison, I think there are plenty of cool fish, eventually.

  31. Jennifer Lynn
    Jennifer Lynn says:

    I’m so sorry to hear about the breakup. That sucks.

    But my mom always says, “When someone tells you who they are, believe them.” [she is a genius]

  32. Eileen
    Eileen says:

    I’m very sorry for your loss. But it appears this guy is not treating you right, and you don’t feel good in the relationship. Every relationship either energizes you, or depletes you (think about it, it’s true). It’s clear from your comments here this is a depleting relationship, that often leaves you feeling BAD. Whoever you are with, you need to feel GOOD.

    Don’t be so hard on yourself about this relationship. THANK YOUR LUCKY STARS you’re getting out NOW, and that you’re not married to this guy! Often, looking back, you can see the signs of how someone will treat you much earlier than you imagine.

    I remember clearly your discomfort when he peed in the front yard ON THE FIRST DATE. To me, that said, “I’m all about MYSELF and MY feelings,” as opposed to caring about YOU and YOUR feelings. Is it any wonder this guy hasn’t been in a relationship longer than four months?

    Don’t beat yourself up for not recognizing this. Try to use it as a useful learning experience. I once had a similar experience. The biggest thing I learned from it is that I hope to share with my daughter (who is now in her teen years) to NOT waste time with ANY man who starts putting you down, or trying to “control” early in the relationship. It doens’t bode well.

    Good luck.
    Eileen
    Dedicated Elementary Teacher Overseas (in the Middle East)
    elementaryteacher.wordpress.com

  33. Anthony
    Anthony says:

    I had a job interview this week, my first in forever. I didn’t want the job and was using it as a practice interview so I didn’t prepare at all. I only realized how amazing the job was when I got there. Then I got nervous.

    The first day went badly. Very. I knew I wouldn’t get it and I wanted to leave but I soldiered through the second day because that’s just what you do. Second day turned out worse. I’m still recovering from the embarrassment.

    I even did the chocolate bar thing. Twice. Usually helps but not this time.

    So reading about you struggling through your pitch under less than ideal circumstances has cheered me up immensely. If someone as motivated, smart and experienced as yourself has days like this I’m not going to beat myself up over mine.

  34. kat
    kat says:

    I feel your pain. I’m so sorry this happens to you, or to anybody. I’m 23 and kept quiet until recently about the 2 year cyclical dumping by my boyfriend. I could kick myself for all the times I thought of him as my moon and stars when he was really just not ready for a serious relationship. Now, the truth comes out.. he hurt me sooo many times and I’m not going to beg for him to stay with me. Standing up for yourself takes guts.

    Love is not easy and it’s unfair how some men make us choose between our career or our family. I’m still in school, but I hope that one day I can be as professional as you in juggling personal/work life. Thank you for sharing your wisdom through your writing!

  35. Nichole
    Nichole says:

    The divorce thing can often be a catalyst for these continual rebound type relationships. When you’re in these relationships and people tell you they’re rebound, you don’t believe them. But then a few years go by after your divorce, and you look back at all of the reject situations you put yourself in and you’re like “thank god I didn’t stay with that person and thank god he dumped me!” It’s been almost four years now since my divorce, and my measure of success in both personal and professional relationships is this “Am I my best self when surrounded by this person? Does this person or situation inspire me to live my best life and reach my fullest potential the majority of the time?” If the answer is “no,” i now pick up my emotions, without a bat of an eye, and leave. It’s not always easy, but I can tell you now I know how good it feels to be inspired by beautiful and wonderful people.

    Don’t be sad about the farmer, and as my fellow divorced friends and I often say.. date, date, date.. that’s really the best way to get detached from the one who keeps holding you back.

    Also, I can promise you, you will look back at the farmer and have one of those “thank god” moments and also one of those moments where you say to yourself “what was I thinking?” I promise. :)

    Good luck… and date, date, date.

  36. The Gardener
    The Gardener says:

    In both your personal and professional life, you are waiting for the next big relationship – the right guy, the right big investor.

    With regard to you personal life, you know how to pick them, Penelope. First, a guy who wouldn’t do oral sex; next, a 40 year old guy who has never been in a long term relationship.

    Next time, before you elevate them to the level beyond an interesting night out, stop and think about whether the relationship has a chance given the guy’s issues. Once you sort through that, you can figure out whether it has a chance given your own issues (and we all have issues, although yours are just a bit more convoluted and intense than most).

    On the company, I would be kind of pissed if I were one of the Ryans and you were showing up at a major VC opportunity unprepared. Of course, if I were you, I would be annoyed to get there and find out the guy doesn’t even know what site is the company’s.

    Here’s the important part: take a moment and imagine a world where those next big relationships don’t happen. I’m not predicting disaster; I’m just suggesting that you imagine a world where salvation doesn’t come over the hill like the US cavalry in an old western.

    What would a happy Penelope look like if she didn’t have a guy in her life?

    What would a surviving (and thriving) Brazen Careerist look like if that next big drop of investor capital doesn’t come?

    If you are living in a mind set where salvation doesn’t have to come from outside, it’s more likely to find you.

  37. Frank
    Frank says:

    Penelope,
    I love you, man. In a Bud Light sort of way. Because I’m married and happy. But if I weren’t, I’d be looking up your next speaking engagement. As I read today, I wondered, how could a woman with so much confidence in at least some areas of her life, want to try to convince a guy to stay with her? Next time a guy wants to dump you, tell him he can kiss your fine white ass. (Just giving you the benefit of the doubt.)If he has second thoughts and comes back, then you’ve got something to think about. If not, to hell with him. If he does it a second time, put a block on his cell number. Lots of guys out there’d love to hook up with a cute, quick-witted future empire builder. What? Cute’s a bad word? Dang, you ARE harsh.

  38. Amy
    Amy says:

    Why are you still using water-soluble mascara? You can now get both mascara and lipstick that you can SLEEP in and it will still look okay. You should try this, because it is awesome.

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