A single man at 53 with relationship questions

This will give you a good idea of where I’m at beIng single at 53. It’s a trip for sure.


Do you think you will fall in love again?

Do you have the energy to start a love relationship and keep it going?

Do you still get sparks/attracted to someone or do you dismiss it right away?

Do you feel like you could live with someone 24 x 7?

After living alone so long, could you put up with someone around having to talk to, plan things with, accept things that annoy you,…

How would it work dealing with their family?

Do you worry about growing old and alone and not having memories shared with someone?

Are we alone if we live by ourself but have many friends?

Do you crave a hug, your cheek kissed, …?

When was the last time you were intimate? Was it awkward? Were you scared?

Is it different when we don’t feel as attractive now compared to when were younger and more attractive?

Could you trust again?

Would you be walking on egg shells waiting for something to go wrong?

Would it end up being like many couples at restaurants sitting across from each other not talking?

What’s the worse thing that could happen if you tried to find love?

What’s the worst thing that could happen if you don’t try?

It seems to me all this was much easier when we were young. What are your thoughts?

Sending good vibes to you all,


32 responses to “A single man at 53 with relationship questions”

  1. Dwight, you’re not going to like this answer, but only you can answer these questions. What do you want at this stage of your life?if you know, go for it!
    Jim x

    Liked by 3 people

    1. Thanks Jim. It definitely takes some pondering.

      Liked by 1 person

  2. Hey, Dwight,
    In all honesty, it seems to me that you will fall in love again, deal with the ups and downs, the families and the not-so-alone time. You’re far too caring not to! The biggest thing is not to push for it, it will happen as it should. In the meantime, your sobriety continues to shift and strengthen that big ol’ heart of yours. What you had before is not what you will have again!

    Liked by 4 people

  3. Dwight, I don’t think these things were necessarily easier when we were younger, just different. Relationships (old and new) are not easy though, that’s for sure. I’ve been with my husband for 20 years now and there are questions that go around my head all the time. I’m with Jim on this though, only you can answer the questions. Maybe you won’t be able to answer them all until the right situation happens. Whatever, we’re here supporting
    Hugs 🤗

    Liked by 5 people

    1. I think you’re right, Claire. Thank you😊

      Liked by 1 person

  4. I believe when you least expect it, turn a corner, open a door, that “someone” will be there who will make all those questions go away. However, like clairei47 mentioned above, the questions never truly go away, they change, over and over until we are no more. As Jim suggest, why don’t you print these questions out, and answer for yourself, you’d be surprised what pen and paper bring out, as compared to typing on a computer. All the best!

    Liked by 4 people

  5. Dwight, I guess I read the post differently than the other people who commented. I thought you were asking for us to answer your questions and I did, directly to you via email. Because they are questions that I wonder about as well being in a similar situation. I wonder about the male thoughts on those types of questions and would enjoy hearing your answers whether by blog post or email. Some of the questions felt too personal to answer on a blogging comment forum so I didn’t choose to do it.
    But yes, I’d like to find love again with the right person.
    Yes, I think it is different and harder to find love in our 50’s in this day and age with all the social media, online dating apps and prior relationship baggage etc. But I think it’s possible and that’s what keeps me going.
    Have a great day!

    Liked by 5 people

    1. Thank you, Janie. I was looking for feedback from others who could relate and had been or are in this scenario at our age. I welcome all comments though and have gained insights. I’ll email back soon😊👍

      Liked by 3 people

  6. Such good questions! I’m not 53 but going to comment anyway. I was single for a longer time and I had decided not to have any romantic relationship in my life! I was done and finished. I made plans to become a nun in a Buddhist monestary, I wasn’t there yet but was seriously planning and considering it.
    To ‘study’ different monasteries and to learn about Buddhism I traveled a few places. Long story shorter: I met someone who made me laugh so hard. I met him in Tibet of all places and he looked a bit like a monk 🙂 It turned out we lived about 8 km from each other.
    I didn’t want a relationship but I couldn’t let him go either. I had some of your questions. I learned that they are two people in a relationship and that I couldn’t answer those questions alone. I asked them and together we are figuring it all out. But in the first place I choose to be honest and to make the relationship work and to this day I do what I can. I feel like life sometimes happens and it doesn’t care always about our questions.

    Liked by 3 people

    1. Point well taken that life sometimes happens and it doesn’t care about questions. I’m shooting for that and toss my questions to the side.

      Liked by 1 person

      1. I think you can keep them in mind of course. But we change and grow and life happens. It will be a mix of those. Life has surprises!

        Liked by 1 person

  7. Hi Dwight,
    I can only speak for my single friend who is 54. She has been dating, and most of the guys were not good for her.
    However, she kept trying, and is currently with a good guy.
    It takes faith and courage, to be sure, for her to put herself out again, over and over, knowing she might be hurt again.
    But she doesn’t want to live life alone!
    You are such a good guy!

    Liked by 4 people

  8. This was so funny to read, Dwight. Not the ha-ha funny, the other funny because you took the questions right out of my mouth! I wrote a post about never wanting to fall in love again- but it’s because I don’t think most know what it really and truly means to love. I include myself here although I think I’m learning. I also think it’s important to be absolutely comfortable with your own company when no one else is around. I love what kuchaiweb wrote. Someone that makes you laugh real hard is a fantastic start. And yes, a lot of things were easier in our younger days- but we’ve gotten complicated! That’s why we need to find someone to laugh hard with. 🙂

    Liked by 2 people

    1. I totally agree, Elizabeth. I’m ready to love and laugh.

      Liked by 1 person

      1. You even voiced questions I had but had never actually put into words! I’m def going to copy them and doing some exploring! Especially love the one about living with someone 24/7. Thank you, Dwight!

        Liked by 2 people

  9. Hmmm I have a thought on this, who ever she is she will be one very lucky lady xox

    Liked by 3 people

      1. Get a room guys (said quite seriously, and with much love for two such beautiful people) 😉😁


  10. I was single and bringing up my children for 12 years. I yearned for someone, someone who really was my other half. I found him, in the end. But you’re right, things are easier when we’re young. His divorce and ex wife have caused so many problems for us that it has tainted everything. Time doesn’t necessarily heal the damage caused. I imagined life would be different … it’s so darn complicated and often I yearn for those simple days of being alone.

    Liked by 2 people

    1. Hey Katie. I never knew you were single for 12 years. Thanks for the comment and hope you’re doing well. How’s NYC going? Are you getting into the swing of things here in the States?

      Liked by 1 person

      1. All is good thanks. Sometimes it can be quite lonely not having family and old friends close by, but there’s always something going on … my husbands work involves lots of social events, so I’m kept busy which is helpful.

        Liked by 1 person

  11. I can see why anyone alone in their fifties would have serious considerations/reservations about future relationships. I left my first husband when I was 39 and never ever planned to remarry (or have another serious relationship). A few years later I met my current husband and we got on the subject and I said I only, and very rarely, go on a date – and only with guys I didn’t really care for because I didn’t want to marry another ass. He told me to quit dating asses and I wouldn’t have to worry about marrying one. Really dumb but I would never have thought of that. 🙄. We started dating, got married. I’m glad 🥰

    Liked by 3 people

  12. It was so cool to read kachaiweb’s comment… because I was going to reply with some kind of musing on the Buddhist idea of true love. I am married 18+ years, and mostly contentedly so, but yes marriage has ups and downs, and I was definitely feeling at one point that I wanted to become a Buddhist nun… I’m not actually joking, though likely that sounds hilarious to anyone who knows me or my blog a little. I am quite far from that peak, to say the least.

    But I like this idea of non-desire, personal detachment, alongside love for everyone. And I definitely have passed through states in which desire-based love was very very faded away… but lately I’m finding that romantic love is rekindled. Guess it goes in waves, and also menopause has some influence. Anyway, Dwight, you are one lovely human being, and someone would be lucky to be in a relationship with you…

    I think I tell this to everyone who ponders finding a mate… sorry for anyone who’s hearing it again… but just before I’d decided to settle down, I’d happened upon a very kitschy-sounding book in a second-hand store, I bought it as a joke for a friend who loved all things kitsch. It was called “Get Married Now! Finding and Marrying the Right Mate for You” by Hilary Rich, I think it was. Ha! That title!

    Anyway, I started reading it on the bus ride home, and to my surprise, and in spite of the Christian-based language (for a non-religious person like me), so many parts of it made sense… that one should make a list of important qualities, do the work of figuring out exactly what you want in a relationship (as others have said above, and as you are right now in this blog post doing, by collecting opinions etc.), and then to take the necessary steps.

    My husband then was my ex-boyfriend — partly because before that, I had been a confirmed bachelorette (lol) — but a bunch of things clicked and I realized he fit most of my ideals (mainly, because “honest, reliable, makes me laugh, intelligent, similar ideals/beliefs, wants kids, values family” were the top few things on my list), and then I contacted him and was direct about my thoughts (well, I already knew he was into commitment, and interested in me, or at least he had been, when we were together), and we ended up back together, got married, and then after that, we just kept making it work, even when it threatened not to. I know things can always change, but… fingers crossed… :)))

    Sorry for the long comment (but you know I’m a rambler, and I care…)

    Basically, I guess the takeaway might be: make a list, check it twice… then find out who’s less naughty, more nice…. then hope and try for the best. ;)) 🤶🎅🏽

    hugs to you, Dwight 🤗💖

    Liked by 2 people

    1. Sounds like a plan. Sending hugs back. Thank you.

      Liked by 1 person

  13. lol..as soon as i read the title i knew there would be a lot of comments, and i sure enjoyed reading them:)..i haven’t figured it out at 53 either. questions…so many questions…lmao

    Liked by 2 people

  14. I don’t think it’s easier or harder. More that when you are much younger you tend to take greater risks. You may be less wounded. You may think less about pragmatics. Love in midlife doesn’t have to take the same form. Who says you have to get married again or even live together? Rather than thinking of all the ways that things can go wrong, aim first for opening yourself to connection and see what happens.

    Liked by 2 people

    1. Evelyn – Great points and new perspective, thank you!


    2. Hey Evelyn. I just had to tell you this really stuck with me. So much that I’ve probably shared your comments with at least 4 close friends. Thanks again😊


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