Deep Questions (aka: One-Sided Conversations)


It’s been a very long time since I’ve had a good, deep conversation with another human being over the age of 18. Conversations in the workplace tend to stay on the shallow side, which is normal, I suppose, but unfulfilling at times, like snacking on fruit when what you really crave is a thick, juicy steak and a buttery baked potato.


While browsing blogs on WordPress, I came across a post by Wendy, at Brilliance Within, which posed ten great questions that can help you to dig deeper, to get to know other people at a deeper level. Since I lack the social opportunities to use these questions in actual conversations, I thought I’d answer them here, should any other wandering souls want to get to know me a little better:


  • What are you enjoying most about your life at the moment?


At this exact moment, I am enjoying a Netflix Show, called The OA. It is a strange and mysterious program about a young woman who has near-death experiences, and through them is able to reach out and change the lives of other hurting people. But overall, I am enjoying the peace and stability of my life; of raising my children in a decent neighborhood, of working at a job I enjoy, of having good health, and of finding ways to keep learning, keep growing, keep becoming a better version of myself.


  • What’s your biggest fear?


I have two. One is the obvious and unspeakable fear of something bad happening to one of my children.

The other fear was already realized. My best friend, around six years ago, decided that she no longer wanted to be my friend. Before we parted ways, she confessed to me that our friendship had been uneven. I wanted a best friend, and she did not. She had felt for a while that I was like a dog, following her around. Just writing those words – even thinking them, unleashes such a flood of raw emotions that I am still unable to keep myself from crying, and I am a person who rarely cries. I thought that I had been a good friend, and kind, and generous, and loving, and that our friendship was reciprocal. I never knew that I was being too clingy, or that she had perceived me that way. Her words have haunted me so much, that I feel them any time I start to get to know an acquaintance. I am fearful of calling, fearful of texting first, fearful of reaching out to invite anyone to spend time together, because I don’t know how to keep from crossing that invisible boundary that makes people feel as though I am chasing them. When I sense that someone’s interest in me is waning, I run away, because I don’t want to hear those words again. Because of my greatest fear, I have become skilled at remaining cold and aloof, and skilled at letting people go. I have learned how to be content with loneliness instead of trying to build relationships.


  • What do you regret most?


This is related to #2, and cannot be expressed here.


  • What did you dream about doing when you were a child?


I dreamt of being a children’s book author (still working on that one) and a tap dancer (no thanks, haha). I also resolved around the age of ten that I would never get married, and would adopt a bunch of kids and drive a bike instead of a car (which I did until I finally got a driver’s license at the age of 26).


  • How do you feel about your job? What would be your ‘dream job?


I’m crazy about my job. It covers my favorite aspects of IT (creating, building, and administering computer systems and supporting users of those systems). I also hope to have my young adult novels published someday in the not-too-distant future, but my day job is perfect for me, and I look forward to doing it each day. The only thing that would make it even better is to be in a position where I can use my leadership talent and skills at my job, which I intend to work my way toward.


  • Where do you see yourself in 5 years’ time?


Hopefully in that position of leadership (see #4). I also see myself as a soon-to-be single empty-nester, as my youngest kid will be on the verge of graduating high school and heading off to university. That is a pretty lonely vision. It is hard to imagine life without my children.


  • If you could choose 1 place in the world to travel to – where would it be?


Only one? Seriously? My list is sooo long! Okay, then, I will have to choose England, so that I can travel to the places in the Harry Potter and Jane Austen and Charles Dickens and Shakespeare stories that I love so fondly.



  • What is your ‘vision’ for your life?


I don’t have one all-encompassing vision. Just a series of smaller goals. Raise my children to be kind, caring, educated adults who contribute to society in positive ways and are content with their lives. See my future grandchildren grow up. Keep working hard at and enjoying my career. Keep finding ways to learn and grow and experience the good things in life. Share my stories with the world. Travel a lot.


  • How could you enhance your relationships/life?


I don’t know. Unless #2 magically fades away, I don’t believe that I will ever develop any close relationships beyond those with my children.


  • When do you feel you’re happiest/saddest/most in love?


I suppose I am happiest when everything feels at peace, like when reading a good book while lying on a warm, sunny beach while my children play nearby. Saddest when the darkness is too dark and the night lasts far too long.


Please feel free to answer questions in the comments below. After all, the point of asking deep questions is to start an authentic conversation, and to get to know other human beings.


9 responses to “Deep Questions (aka: One-Sided Conversations)

  1. The second of your biggest fears breaks my heart sweetie. If I could I’d give you a huge hug right this very minute. Otherwise, I like the theme of this post but my answers will require some mulling…I’ll get back to you on that. Consider yourself hugged!

  2. Okay, so being President’s Day and the Bosses being who they are we’re in the office but quite slow so I’ve answered the questions. However, I wanted to be sure you really, truly wanted them posted in your comments as some are quite lengthy. ; )

  3. Here goes nothing!

    What are you enjoying most about your life at the moment? Playing with my dogs. No, really. I LOVE coming home to a house with dogs in it! When Kohl trots up and dumps a well-chewed Kong Wubba toy in my lap I know I’m loved. If only for my mad tug of war skills!

    What’s your biggest fear? I can only list one?!

    What do you regret most? Not being emotionally stronger as a young woman. I’m not sure how I could have changed that or whether I would change it now if I could. But I often wonder if I’d been a stronger person would I have felt I had to marry my first husband? As an adolescent I was not attractive according to the standard of the day. When my grandmother arranged for me to meet the grandson of her friend it seemed like it was meant to be. I can’t say I was swept away but he was the first man to show me any real attention, and at 21 I was desperate for that, and for…well, not love per se, but what I thought love was. Does that make sense? I didn’t think I had much to offer and part of me jumped on the marriage as my only hope to avoid a lonely future. Being single a while longer wouldn’t have been the end of the world but I didn’t know it then. Besides, without that relationship I wouldn’t have any of my children and that doesn’t bear thinking about.

    What did you dream about doing when you were a child? I wish I could remember first, whether I dreamed and second what my dreams were.

    How do you feel about your job? What would be your ‘dream’ job? I love my job, most of the time. I work with and for some wonderful people locally. The Powers That Be in our corporate office though often rain on that parade, making it harder to enjoy what I do. I’ve often wondered what it would be like to be a librarian. As a child I loved books and I spent many summer vacations scouring the library for new titles to read. I’m not sure why it never occurred to me to be a librarian but in my imagination that seems like it would be a phenomenal job.

    Where do you see yourself in 5 years’ time? I’m afraid I’ll still be here at my desk, pounding the computer keys and coordinating workflow for the shared services team I lead. Unless I win the lottery or come into some inheritance from a long lost relative I won’t be able to pay off the loans I’ve taken from my retirement account. Until I pay those off there won’t be any point in retiring. Even if I do manage to pay those off, unless there are lottery winnings leftover, retirement is something of a dream. I didn’t plan very well for my later years (biggest fear anyone?) and I’m looking down the barrel of the future with trepidation.

    If you could choose 1 place in the world to travel to – where would it be? I’m pretty boring; I’ve never had a bug to travel.

    What is your ‘vision’ for your life? I’m not sure I have a vision for my life. Peace maybe. I’d like there to be peace in my life. I’m tired of hearing my husband whine about how much better off his sister had it when they were kids. I’m tired of hearing my two estranged daughters’ making excuses for their choices and complaining that everyone’s against them. I’m just plain tired of strife – can’t a gal just have a Calgon moment every once in a while?

    How would you enhance your relationships/life? I started to answer this flippantly but it occurs to me it’s a serious response – I’d take more time for myself. Maybe I should clarify that. I’d take more “alone time” to let my brain recharge so I can be a better wife, mother, friend. I’m constantly pulled in multiple directions and I rarely get any time just for me. If I don’t take care of me then I’m not going to be able to contribute very well to my relationships am I?

    When do you feel you’re happiest/saddest/most in love? Happiest – when I wake up before the alarm but then realize it’s Saturday – no lie. Sleeping in is my most favorite thing! Saddest – when I think about my mom passing before I could see her one last time to tell her I was sorry. Most in love – when JD does something for me that is completely unexpected and out of character. Example: for a while there work was so freaking busy I was staying late every night and some of my household chores were suffering. He helps with a lot – washes dishes, does laundry, starts dinner or picks it up, etc. One thing he’s not been a fan of doing and I haven’t asked him to do (other than post-knee surgery) is clean the cat box. Coming home late to find a fresh litter box (we use Feline Pine and it smells like a forest the first hour or so it’s poured out) was amazing! And it happened more than once! I do love that man, even if he is a whiner. 😀

    • I also used to wonder about being a librarian, until one day, I learned how tight that job market is, and figured it wouldn’t be worth it. But yes, many childhood days at the public library, reading and enjoying the kids’ programs.

      Ahh, you are so lucky to come home to your dogs. 🙂 I miss having a dog, but my current landlord doesn’t allow them.

      ” Being single a while longer wouldn’t have been the end of the world but I didn’t know it then…” Same. I was also a 21yo naïve bride. But luckily, I got some amazing children out of that doomed union.

      High five — I am all for those peaceful Calgon moments! I’ve taken to enjoying frequent soaks in the health club Jacuzzi for that very reason. Thanks so much for sharing!

  4. Have you ever read Big Little Lies by Liane Moriarty? Your fear reminded me of one of the events in this book and with the right friendships the character was ‘getting over’ this event. I wish the same for you. Love aiming for deeper conversations, I might answer these question in a blog one day…

  5. My feeble attempt to update the conversation starters:

    What makes you feel most alive? —- Have you ever considered suicide? What method first came to mind? Did you think of those you’d be leaving behind? What made you abandon the idea?

    Have you ever cried in public? —- Were your last tears of happiness or sadness? Do you choke up over fictional characters?

    Do you read reviews before you see movies? —- Have you ever become distracted because you were aware of the camera angles, pans and direction in a T.V. show or movie? Kind of like Linus being aware of his tongue.

    Do you say sherbet or sherbert? —- Does anybody know what that stuff is? Do you call them Quepons? We can’t be friends!

    Have you ever had a paranormal experience? —- How do you define normal?

    What do you usually get from the ice cream truck? —- Do you eat ice cream or drink beer in the winter?

    What was you high school gym teacher like? —- Did you have to take group showers after gym class?

    How do you feel about cilantro? —- Do you remember when you couldn’t find a good Mexican or Indian restaurant? Do you think ketchup is spicy?

    • Honestly, most of these would lead toward a far more interesting conversation than, “So, what are your hobbies? How old are your kids? What do you do for work?”

      What do I order from the ice cream truck? Nothing. I’m not a big fan of ice cream. Too cold. *Shivers*

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