How to make a genuine connection with anyone

My friend Melissa is gone. It’s been two weeks since her visit ended, but I’m still so sad. I’m not sure if I’m sad because I’m really lonely and isolated on the farm or if I’m sad because I fell in love with Melissa.

I miss her taking pictures all the time. For example this self-portrait. Which she took 500 versions of. She wore the same clothes for a week— something that feels natural to do on a farm—and even though the paint is red and her clothes are pink, she magically matches my bathroom walls.

She left me with a folder of 50 photos for my blog. That’s a good gift. And she left my kids with the feeling that they made a new friend.

I took this photo from the front seat. I told her maybe I didn’t like it. She looks sad. But she said, “We were sad. It’s a sad movie. The Dalmatians are being turned into coats!”

I wish I were gay, and attracted to people less than half my height, because then I could marry Melissa and she’d never leave. But she cannot live here. She needs to get married.

She wants kids. And I don’t think she will find a husband on our farm, although I have to say our plumber is smart and sweet and hot in a country-boy kind of way. But he’s married.

Now that she’s gone, I’m sort of sinking into a depression. And lately, all my depressions look like this: The farmer does not pay enough attention to me. Blah. And my career does not seem to have a rocket ship trajectory. Blah.

But if career paths are really learning paths rather than earning paths, then my career is about learning to make connections. And maybe I do have a rocket.

1. Watch for personal patterns in moments of failure and success.

I have built three Internet companies based on communities of math teachers, then city managers, and finally young professionals. And I have built a writing career on documenting how I sort out the rules of engagement in life.

You can see how far I’ve come because my first big break in writing was when my hypertext (which is here) got me lecture gigs at Brown University and the University of Paris. Publisher’s Weekly bitched about my inability to be emotionally connected in my writing, but I got into graduate school at Boston University for my cunning ability to describe really bad sex.

I wonder if my editor will cut that part.

2. Focus on one person at a time.

The thing about writing for an editor is that you write for one person. Did you ever get coached for speaking? I did — the TAI Group. I love them. They gave me incredible coaching and if I had to get a job that was commission-based and made me scared my kids would starve if I couldn’t make a sale, I would choose to sell speaking coaching from the TAI Group.

TAI taught me that you have to connect with a single person in the audience. Talk to that one person until you know you have made a deep connection. And then move to another person. Do not scan the audience trying to connect with everyone. If you try to connect with everyone, you connect with no one. If you connect deeply with one person, the whole audience can feel that connection and they actually feel connected to you.

Really. This works. It’s super hard to do because our intuition is to ditch someone before we make a connection because it’s so scary in a speech to try so hard, in front of everyone.

Speech-making mirrors life. We must risk making deep connections. This would be a good jumping off point for a post about intimacy but I fear I have no ability to understand intimacy, so instead this will be a jumping off point for writing for an editor.

If I write for him, with him in mind, then I connect with him really well, and, in turn, connect with you—just like in the speech.

Right now, I am stressing because my editor might cut all this stuff. About connection. So I have to write more.

3. Have patience while you look for an engagement point.

I’m becoming fascinated with how people make connections. So much of it, I think, is that you assume people will be interesting. Moira Gunn has a show on NPR called TechNation where she interviews scientists about topics she knows nothing about. She is renowned for knowing how to start a conversation with anyone.

Gunn gently steers the person to a place where they can make a connection. One of Gunn’s favorite interviews was with a food safety researcher who ended up talking about mussels. He told her that you are only supposed to eat them in months that have Rs in them, because in June, July and August the water is warm and bacteria levels go up, and mussels are basically filters.

Melissa met me by stalking me at a conference where I was speaking. I thought I was avoiding her, but she waited until I was clearly lost trying to find the room where I was to speak. She said, “You look lost. I can get you to your room.”

4. Say something simple and true.

People who say they are shy are usually not shy, but rather, they are under the impression that they have to say something genius and complicated and impressive as an opener, according to Bernardo Carducci from the Shyness Research Institute. But in fact, people like openings that are simple and true—these openers have plenty emotional and intellectual space to join in.

I’m smitten with Joel Johnson’s bio page. Look at it. He’s done incredible stuff, but he uses the page to create space for the reader to join him—in an e.e. cummings sort of way. There is something about the combination of lists of achievements and fully-formed sentences that pushes a reader away. Roland Barthes writes about how the connection between the reader and the writer is in the white spaces on the page, not the text. If this is true, which I think it is, then Joel has one of the best bios for making real connections that I’ve ever read.

He makes me want to change my bio, but honestly, I’m scared to make my bio more about connecting and less about me because I want to make sure people know how great I am. It’s a personal failing.

Note, that last line is not something simple and true. It is perhaps a partial-truth.

5. Practice.

Anything you want to be good at requires that you do it over and over again, and Carducci says that creating a good opener for conversation is no exception. Here’s his book, for those of you who are operating under the delusion that reading about something is a replacement for real-life practice.


I miss Melissa.

67 replies
  1. Wayne Allen
    Wayne Allen says:

    Hey Penelope,
    I’m wondering, do you miss Melissa, or do you miss how you chose to be while being with Melissa?
    If the former, you are stuck, if the latter, then you know the way out when you choose to start depressing yourself!
    Warm thoughts on “V” Day!

  2. Rita
    Rita says:

    Penelope, each time I read your posts I come away gaining something new and different. You’re brilliant. I am so sorry that your heart it hurting. I had a therapist who told me once (as simplistic as this sounds), “you have felt good and you will feel good again.” Peace, give yourself the time and space..

  3. Lauren
    Lauren says:

    ” It's super hard to do because our intuition is to ditch someone before we make a connection because it's so scary”

    This is true not only in speech writing but in all human interactions. I love Penelope’s writing because she so often makes profound statements about the world using the minutia of everyday life. People connect with Penelope because she is courageous enough to discuss the minutia.

  4. Erica Peters
    Erica Peters says:

    The problem with “cunning” is not that it’s too risqué, it’s that it’s too tired, too much of a cliché.

    This is great: “you have to connect with a single person in the audience. Talk to that one person until you know you have made a deep connection.” Brilliant and immediately useful.

    If you were really focusing on writing for your editor, would you write this line: “Right now, I am stressing that he’ll cut all this stuff.”? Maybe you would… But me, I think you were writing the post for Melissa, not for your editor. Which is fine, except that Melissa has been hanging out with you, finishing your sentences and vice versa, so you can assume that she sees your point immediately…which is perhaps not true of the rest of us reading along at home.

    I didn’t understand your point about Joel Johnson. It’s cute, but really hard to read. And you talk about the white space on the page, but the only white space on that page is the words themselves… which seems odd, not welcoming. Could you explain if you really see this page as creating space for the reader to join Joel? And if so, how so?

    Also, two comments unrelated to this post:
    1) My yellow disk just arrived (except in my case it's green) – €“ yay! So fun to stand on. Thanks!

    2) Following up about the Volkswagon Force ad, in case this hasn’t been mentioned here:
    “Volkswagen … managed to get more than 10 million people to watch its minute-long ad [before the game]… And then cut the ad's time in half and played the shorter version during the game. Since a thirty-second spot during the Super Bowl ran for $3 million, Volkswagen saved itself another $3 million by playing just the thirty-second ad.”

    • Penelope Trunk
      Penelope Trunk says:

      Erica, I think you’re right about cunning. As a pun, it is stupid. So I deleted that paragraph. I think the post works fine without it.

      Thanks for the good edit.


    • Jennifer Ellis
      Jennifer Ellis says:

      I completely disagree about the post being unclear if you are not Melissa and with your point about Joel Johnson.

      • Erica Peters
        Erica Peters says:

        So, you think the post was clearly not aimed at Melissa. Cool. And you understand the point PT was making by pointing at Joel Johnson’s bio. Great. Can you explain to me how the use of white space on Joel’s bio is inviting? ’cause I still don’t see it.

  5. Jean Gogolin
    Jean Gogolin says:

    So ironic that you would would write “I feel I have no ability to understand intimacy” in a post about falling in love with, and missing, Melissa. I loved this post.

  6. Sheryl
    Sheryl says:

    This post reminds me of being out for dinner last night with my husband. He ordered a mojito, and I ordered scotch on the rocks. He took a few sips of his mojito and noted that he couldn’t taste rum in it. He asked our waiter to have the bartender make it again. The second mojito came and it tasted fine. Then I ordered a second scotch on the rocks and got a tumbler full of scotch with a few ice cubes in it (this in Utah, where it’s illegal to serve more than an ounce). I think your editor did a version of the bartender’s trick with this post.

  7. Bryan Thompson
    Bryan Thompson says:

    Penelope, I like how you wove your connection speech in with the story of your friend. You have a way with words. I have been communicating through writing and speaking for about 10 years. As a pastor, it is absolutely crucial (at least if we want to do it right) that we connect in massive ways (public talks) and in the smallest, intimate ways (one on one conversations). I would add “be a better listener.” There’s no arriving point on that one. We can always aim for better. Thank you for your post!

  8. Jennifer
    Jennifer says:

    I find that attachment and loss are really hard for me too when the rare people I trust live far away. When I get to participate in regular shared experience with someone I’m attached to, I feel calmed and secure; it is incredibly healing. When friends live far away, not getting to experience them physically is painful. I have to remember that when someone I need is far away, not to be angry at them for abandoning me. Its easier to be mad at them then really feel the sad. When I miss them, its really visceral, a deep body ache. Thank you for sharing your sad.

  9. GeneratonXpert
    GeneratonXpert says:

    I think you need to remember that you are where you are right now, because that’s where you’re supposed to be. Living in the moment, in the present, is really hard. But that’s how you learn the most.

  10. Kathy
    Kathy says:

    Your posts always make me feel or see something I didn’t realize I was missing. For instance, how important it is to have a deep connection to someone even when you know that they eventually will have to leave you. I hope to someday have a friend that means that much to me. In the meantime, Penelope, spring is coming to the farm. May the thought of that lift your spirits.

  11. Mark W.
    Mark W. says:

    IMO, just right as far as the content of the photos and the amount of photos for this post is concerned.
    I like the way the second and third photos were woven together with the text. Each photo showed in different ways how your kids made a new friend/connection.

  12. Lisa
    Lisa says:

    Maybe you could rotate *us* in. Two weeks at a time. One might argue, by the way, that you are the best on the Internet at making a genuine connection with your writing. If one correctly parses genuine, and connection. I hope the coming spring lifts your lonely heart.

    • Penelope Trunk
      Penelope Trunk says:

      That’s interesting. I have thought seriously about this. I think about seeing if people want to come here to visit. There’s an extra bedroom. And the farm is fun. I wonder what would happen… like, if no one would come, or only psychos would come.

      The farmer has sort of said it would be okay… So I’m thinking.


      • Margaret Goerig
        Margaret Goerig says:

        I would come. And I’m pretty sure I’m not a psycho. I mean, I’m still really embarrassed for telling you to listen to “Teeth” that one time, because that’s probably not a song you should recommend to someone you’ve never met, but I think the fact that I am embarrassed about that means that I am not a psycho. I should be passing through Madison in about four months, too. Maybe our dogs could have a play date.

      • Jennifer Ellis
        Jennifer Ellis says:

        I would seriously consider coming. But I would be afraid I wouldn’t be interesting or engaging enough.

      • tiger
        tiger says:

        i’d come in a heartbeat. but i think i’d probably fall in love with you, if i haven’t already, and that might just be awkward. of course, you could pretend you were into me too and maybe that way we could make the farmer jealous and maybe that would solve that problem for you.

  13. Irving Podolsky
    Irving Podolsky says:

    As usual, P, you have published a post covering eight juicy topics. Okay, this time less. But I had to choose a comment issue, and I did. Here’s an idea about connecting with people within conversations.

    There are individuals in my life who are not really interested in what I have to say. They use our discussion to make me interested in what THEY have to say. Talk about a disconnect! So my suggestion is this: For a real connection, you should, no you must, sincerely WANT TO KNOW the person facing you. You need to care about them, even if you disagree with their ideas. And if you’re not that close, find something about that person you CAN admire – some common ground. You can’t fake this symbiosis, unless… Unless your conversation buddies don’t care about you. If they only care about your impression of THEM, about THEIR WORLD, you can easily feign interest and manipulate their impressions of YOU. How? By laughing at their dumb jokes, by nodding at the appropriate moments, by agreeing with them…about everything. This I call “Workplace Cooperation.” It’s phony as hell and it keeps the wheels of society turning world wide.

    Sad but true. And I hate to admit, I also use this tactic. Is it cunning? I’d say so.


  14. BrendaH
    BrendaH says:

    Mark W said ‘One might argue, by the way, that you are the best on the Internet at making a genuine connection with your writing. If one correctly parses genuine, and connection.’ I have to agree. Sometimes I think you are too cerebral to actually connect with the Farmer…yet here you connect beautifully with all of us…who don’t live with you.

  15. Paul Basile
    Paul Basile says:

    Small world – I didn’t know you had a TAI experience in your background. I have been a big fan of TAI for a long time – and possibly the biggest suppliers of clients to them. Gifford performs magic – except then you find that it’s all real. They know about connections at TAI. Sometimes the world is even small physically: I now have moved from Paris and live in NYC exactly two blocks west of TAI.

  16. Tzipporah
    Tzipporah says:

    Why is it that all my best online connections with writers are with people who have Asperger’s? Or various other social issues, like being economists. I think there’s a difference between the emotional/intellectual connection you can develop in person vs. online; for those of us who are interested in ideas, rather than things or events, online connections are just easier.

  17. judy
    judy says:

    First, I know writers have editors, and supposedly have to please their editors, but mostly you need to be true to yourself. Otherwise, why bother?

    Secondly, I don’t especially like the advice about connecting to ONE or TWO people in the audience. If I were one of those people, I would probably feel very uncomfortable, uneasy. (Maybe it’s just me.) I say, talk to everyone! Make sure the rest of the audience isn’t feeling neglected!

  18. Harriet May
    Harriet May says:

    I wish I could come visit you. But I’ll admit I’d be scared. I think too much about what people think of me and sometimes I find it debilitating. Sometimes I take far too long to write simple emails, for example, just in case I come across all wrong. And I have a fear of being deathly boring. Well, perhaps I’m not, not completely, but remember how I compartmentalize too much? My boring self is the one that comes out first. And I would hate for you to think I was boring. In fact, I don’t think I could stand it. The key, I think, is to be drunk. My drunk self is my most open self, but then, isn’t that true for everyone?

  19. John G
    John G says:

    If your editor is a cunning linguist he would enjoy a good pun, but I think he should take out the part where you uncover it for all the world to see. Modesty is appealing, like a hidden treasure.

  20. Stacy
    Stacy says:

    I am sorry you are missing Melissa. I love your blog and the things you write and the pictures. I hope that you find your rocket ship trajectory. Let me know if I can help.

  21. Stephani
    Stephani says:

    I think you have a knack for letting people in. That’s what creates intimacy. So we’re all drawn to your posts and come back for more. You’re a fabulous writer and that’s an outlet you shouldn’t give up. But I love that you’re challenging yourself and enhancing your posts by learning photography and adding your unique Penelope-esque images. Maybe you could make the leap to video and give a us a short handheld tour of the farm from your perspective: inside, outside, interesting objects you love, animals on the farm, your boys in action…a moment with the farmer doing his work. Maybe some of the town folks, and your assistant, I’d love to meet them. Talking to the camera might be a nice outlet for you…cathartic in some way. Even if you don’t post it you may gain something from the experience. And, most importantly, you will have documented this interesting chapter of your life in yet another way. I’d tune in!

    As a New Englander I also want to weigh in and say this winter has been extreme and many of us are feeling blue from being shut in. Cabin fever is very real so cut yourself at least a little slack. And thank God for spring and mini getaways where there’s sun!!

  22. Derek Rubio
    Derek Rubio says:

    What rubbish!
    This whole article -like, it seems, a lot of them here- presumes that the author alone has the power to determine the outcome of a particular activity (in this case, trying to create a connection). Very humble! No mystery, no uncertainty, no question of why one would want to create all these connections in the first place (but we all know why, don’t we?- just to make more money and get ahead in life). No, you just apply the technique & away you go, brazenly successful!
    I love the numerous american people I have got to know and am able to call friends. I see many good traits in americans generally- goodwill, diligence, team-work to name just a few. But this post has that most annoying trait, namely seeking to reduce everything in life to a bullet-pointed procedure- ‘life for dummies, by lists’.
    I commend a long period of silence, preferably in peace & quiet away from communication devices & all the other ‘noise’ in your life, in which to seek a truer, more authentic voice.

  23. Susie
    Susie says:

    Right before I read your post (which I enjoyed immensely, as always) I read a teeny post in my Facebook about how camels only sleep 20 minutes a night. I decided you must have caught on to that trick, Penelope, because otherwise how on earth do you think so much, and then write it down for us, to boot!

  24. Deena McClusky
    Deena McClusky says:

    “3. Have patience while you look for an engagement point.”
    I think this is a great point but because I know that I am really bad at this I actually find it easier to do it in reverse. I give other people the opening. Whether it is my tattoo, or a somewhat unusual or outrageous piece of jewelry clothing, I give them the engagement point to speak to me. I do this not out of the need to stroke my vanity, because I actually hate having the focus on me, but out of my self-awareness about being bad at striking up conversations with others.

  25. Tom Meitner
    Tom Meitner says:

    I just want to say that this is beautiful, Penelope. I actually am probably going to rip off the “careers are learning paths, not earning paths” quote you used there. Life in general is that way – we focus so much on the money that we forget about developing the meaningful relationships that make life worth living. Great stuff here!

  26. Joanna
    Joanna says:

    I thought you might enjoy a non-self-help book take on intimacy–check out Max De Pree’s (former CEO at Herman Miller) Leadership is an Art and Leadership Jazz. And really, not because I work for a research institute with his name, because it is a good book about intimacy, and work, and connection, and becoming what we can be.

    I blogged on a section he wrote on intimacy here:

    and I think intimacy is about a sense of belonging more than anything, which it sounds like you are beginning to find.

  27. Stephen Pendar
    Stephen Pendar says:

    I find your last point the most important. Majority of people are not naturals at socializing, and most do not realize it is a skill that can be developed. What I find to work best is a simple question such as “How’s you day?” or “What have you been up to today?” Then simply ask follow up questions on anything they mention. Keep at it and it gets easier. I blogged on this subject here:

  28. Irina I
    Irina I says:

    This post reminds me of this character Lucy in No Strings Attached. She’s the main character’s sexy boss and at the end of the film, she finally almost gets to sleep with him. And as he’s kissing her, she keeps narrating. “I can’t believe this is actually happening…Oh, that was awkward how I just did that…”, etc.

    And you narrate as you write this post. It’s like this:
    piece of content –> reflection on your content –> narration of your reflection.

    I think that’s awesome. And very sexy.

    • Tom
      Tom says:

      Great insight Irina, thank you. That is true and awesome.

      One of the reasons I’m so infatuated with Penelope’s blogs is that she manages to touch me and so many others by being straightforward. I am not by nature too direct and use other ways, but I just love how she does it. Great learning, for me.


  29. me
    me says:

    Sis, I wish a bunch of us could come over & hang out with you on your porch. And play with the baby goats.

    I miss having real connections with a few special people. Seems the older I get, the more superficial things become ….

    This has been a long cold winter & I could really use a relaxing Saturday afternoon on the farm with good company …. (but only in July, of course).

  30. Celine
    Celine says:

    Like many who have said this before, including your own tweets, it’s time to cut your losses and leave the farmer. It appears that he does nothing to improve your life and living isolated on the farm is making your depression worse. Go back to a city (not necessarily NYC) where you can thrive. It sounds like you’re withering up and dying.

  31. c
    c says:

    adrienne, One answer to your dilemma is to live in a medium size city part-time (i know you will find a way to do this) your ex-husband will have the kids and you can spend some time in the city or stay with one of your friends with/w/o your kids. Also, i don’t think you have asperger’s syndrome, I hope I don’t offend you but, I think you did not have a normal emotional develop due to your parents (esp. your father) and at some point you will or have realized your parents are not role models and need help which is no reflection on you. I hope you don’t feel any guilt and if you do you should analyze what your parent’s shortcomings are! So many of us need to realize this.

  32. Dimi
    Dimi says:

    can anyone explain to me why we should watch for personal patterns in moments of failure and success? I didn’t understand how you can use this knowledge afterwards :-(

  33. Anonymous in case my friend reads this
    Anonymous in case my friend reads this says:

    Is Melissa really looking for an ENTJ, per your tweet a few weeks ago? I have an ENTP-but-can-act-like-a-J-when-needed friend who she might get along with well, and I think he’s finally ready to settle down. Years ago we were friends with benefits and he’s witty, geeky but very socially charming, and well-endowed.

    One of my favourite Myers-Briggs stories comes from him. When he was working at McKinsey they did a team session on MBTI and the facilitator asked a very J colleague if the money in his wallet was organized sequentially. Perplexed by the question, the J said “not in serial number order.”

    Anyway, I hope you feel less lonely soon.

  34. Mitzi
    Mitzi says:

    When I observe your unfolding life through your blog you are helping me understand my 10 year old daughter in a much deeper way. You let me see from hindsight what it is that crosses your mind. She is a ponderer, she has for years had a head filled with wonder and has lived usurping and tilting away at the idomatic windmills of illogical units of expression that most non asperger people never seem bothered to question but just go on accepting the status qou as it is. She has a very literal way of seeing the world which has me explaining lots. She is the love of my life. The most brilliant inquisitive darling a mother could have hoped for and she kepts me honest and with integrity in focus shapes me into a better human being. You too are like that for the rest of us. Love you. Mitzi Egnatz

  35. Dereks
    Dereks says:

    “I got into graduate school at Boston University for my cunning ability to describe really bad sex.”

    Is it available anywhere? I’d read that essay…

  36. Mikalee Byerman
    Mikalee Byerman says:

    I miss Melissa too. Well, my Melissa. I think everyone has a “Melissa” who just makes them feel better; not necessarily about anything in particular, just better in general.

    I’ve struggled with my bio page as well — I think it’s important that the tone of the page mimic the tone of your blog/website. While I’ve not read Joel Johnson’s, I can probably guess what his site is like!

    Fun post — I’m a new reader and look forward to catching up.

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  39. moya
    moya says:

    I think you could have a few trailer homes on the farm so city children or anyone could go to experience farm life for a while- see the animals, feed them collect the eggs or help the farmer a little. Then you wouldnt be so lonely and your kids would have lots new friends??

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