50 thoughts on “Ask Me Anything

  1. 1)Where are you from?

    2) What is your real name? You can just give your first name, you don’t have to give your full name.

    3) What motivates you?

    4) What is your greatest accomplishment?

  2. I have a friend who is 35+ now and always struggles to find girls to date, he himself labels himself a 3-4 on the looks scale but says he should be able to land a girl who is a 8-9 because he has other not so good looking friends who have done the same.
    I’m curious to know if maybe your expectations of the girl you want to date are too high and because of that you aren’t giving the girls who would like you a chance. So instead you go on dates that end up with no second date. I had a type that I dated (and it always ended badly) and I am now married to a guy who is nothing like those men as I realized I needed to change what I wanted.

    • I don’t think I have high expectations – single, attractive, right personality and sense of humor, and interested in me. That seems to be the elusive combination and I don’t think that’s asking too much. If there are girls out there that would be interested in me but I’m somehow missing out on, I’d like to know who they are.

      • Well it depends if your level of attraction equates to a model or a normal looking cute female. It would be really interesting though if you tried going on dates with girls not quite your normal type. Unless you already have.. like I always dated tall guys but dated a not so tall one and he was great. It didn’t work out for us because I was still hung up on an ex but he’s still my friend today.

  3. This probably isn’t important have you gone to college and attained a degree? What do you do for a living or at least what industry? Also you haven’t talked about your family in a while, are you going to do a post about them?

  4. Readers might like to revisit the interview you did with me that showed a partial face 🙂
    https://unleashingthecougar.com/2018/04/15/interview-with-the-formerly-unfortunate-virgin/
    I’ve asked you a hundred questions over time, but perhaps what interests me most is your perspective on the differences between men and women on how they see dates, first meets, text or phone chats – any observations? I know it’s a bit generic, but I really enjoy seeing how men often view things from a different perspective! No holds barred! We’ve already come to blows over your idea that if a woman doesn’t reveal a whole body shot it means she’s fat! (lol – joke intended). And I second the idea of remaining anonymous.

  5. Can you make all of these in to a blog post? The comment section isn’t always the most reader-friendly format.

    I notice you consider losing virginity a great accomplishment. Was sex all you had it cracked up to be? Are there any regrets in spending such a big part of your life focusing on just the one thing?

    • That’s an idea. I may compile all the questions and answers into a post down the road.

      I consider losing my virginity a great accomplishment mostly because it was so damn hard to do. But the real goal is and always has been finding someone to be with. That’ll my next great accomplishment. First-time sex was disappointing, but it go better and better as I went along. I’ve still only done it less than 20 times in total, so it’ll likely get even better.

  6. Outside of dating and blogging what are you pasttimes? Also you’ve talked about traveling on this blog occasionally any places you’d like to travel to in the near future?

  7. Hi, I love your blog and always interested in seeing how things are going for you.

    What three qualities are you looking for in a potential match… Like what things are absolutely crucial for you to get things off the ground?

    Here’s a bit of a fun one….. If money and time was not object, what thing would you do with your life? Be it career, hobby or just a passion that you wish you could pursue x

    • Thanks!

      If we’re talking about a serious long-term relationship? Doesn’t have kids and doesn’t want kids is #1 on the list. Otherwise it just isn’t going to work. #2 gotta have the same sense of humor. We have to be able to laugh at the same things, and #3 gotta have a fun-loving, adventurous personality.

      If money and time were no object, I would quit work and learn all the instruments and languages I want, then travel the world.

  8. Okay, my good Lad, field these:

    A. If you do travel to Chicago, do you anticipate an opportunity to visit with the fabulous
    JBlondie/JRidge?
    B. You once referred to matriculating at a “prestigious” college/university in Upstate New York.
    Might you identify that institution?
    C. How is your father’s health at present?
    D. You have mentioned that one of your brothers relocated to North Carolina. To where did the other
    move?
    E. Which of your sisters is considering moving (Maureen with the children?), and to where is she
    thinking of going?
    F. We know of your fiddle proficiency, what are your three other current instruments?
    G. Is there anything of particular interest that has you mulling travel to Connecticut?
    H. How are things with your mother of late?
    I. Lastly—for now 😉—but perhaps most importantly, when are going eating? 🍔

    • A) I do anticipate visiting with her, and maybe even another blogger or two while I’m in the area.

      B) SUNY New Paltz. I don’t remember designating it as “prestigious” but it is pretty rad.

      C) Physical or mental health? I can only speculate on either as I haven’t seen or talked to him in quite some time now.

      D) Actually it was Florida. The other one went to Ohio.

      E) lolz I’ve forgotten what name I gave her in the blog, but my oldest sister (no kids) is definitely leaving for Florida in six weeks. Half my family is going to be out of state now. Sad face.

      F) Piano, drums… and an instrument of the Celtic persuasion 😉

      G) I think Connecticut is a nice state to visit. Not to mention my mother always wanted to see where Katharine Hepburn lived in Old Saybrook.

      H) Mom is doing very well!

      I) Hmm… good question. I’m planning a trip into the city two or three weekends from now to meet a fellow blogger. Fate has thwarted previous attempts, but when I finally make the trip I’m thinking of double booking that day.

      • A. Outstanding! And, yes, as
        we learned above,
        hopefully that trip will
        afford a conclave with
        “Gentleman Jack” Virgin;
        B. ah, yes, New Paltz, New
        York, the fungus on the
        foothills of the Catskill
        Mountains 😉;
        C. I was particularly asking
        after your father’s
        physical health, as some
        time back you had noted
        his cancer diagnosis;
        D. & E. interesting—as they
        age, New York Jews and
        Suffolk County Irish both
        migrate to Florida 😉;
        F. “Celtic persuasion”—like,
        say, the dulcimer?;
        G. indeed, Connecticut is a
        lovely place. So, with her
        interest in the Hepburn
        property, would you take
        your mother along?;
        H. Swell! Is she perchance
        Black Irish?;
        I. well, okay, then. 👌

  9. Some people never experienced certain milestones you had as a teen when they were a teen, such as making out, a first kiss, touching intimately, and having early sexual encounters. What is your advice to those kinds of people who missed out and played catchup? As I certainly didn’t have those in my teenage years.

  10. Love this idea ! I admittedly didn’t read through all the comments, but I want to know what your ideal date would be ? 🙂

    I would ask a racier question, but I figured I’d keep it classy haha 😉

  11. Yay …. you are answering questions! I hope you don’t find mine too snarky or too sappy 🙂
    1. Do you think that you have ever been in love, like romantically, un-platonically, wishing-this-is-a-forever-relationship inlove?
    2. If you are so adamant about not wanting children, have you ever considered having a vasectomy?
    3. This is not a question, more of a musing actually: but virginity (and all the shenanigans on losing it) is so overrated, don’t you think? Once you have gotten rid of it, didn’t you wonder what the fuss had been all about? And that maybe it was the connection with another human being that was the best part of it, after all. And that the penis-in-vagina or the penis-in-the-mouth sex (and other possible permutations) were just an icing on the cake? A very delectable, enjoyable, addicting icing — but icing nonetheless 😉

    • 1. I thought I was in love with my first ever gf in high school, but looking back I don’t think I really was.
      2. I’ve certainly considered, but until I have something of a regular sex life there’s no real need or point in getting one. Besides, I don’t mind using condoms.
      3. Swiping the V-card was one of the best things I’ve ever done, I don’t think it’s overrated at all. At least for me it wasn’t. And I do understand now what all the fuss is about. I’ve definitely been missing out. Life is even better with sex… just too bad I can’t have more of it.

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