Hey Toya, I'm a 47-year-old single woman, never married with 1 child and I've been seeing a 55-year-old man with 1 child in college. I'll start with the back story. 22 years ago we were basically friends with benefits. Looking back in retrospect, I realize he was doing things to show me how he felt about me, but we never actually discussed where we were going with our friendship/relationship. I was 25 then and he was 33. I was a little wild and just blew with the wind when it came to guys.
During a period in which we weren't seeing each other, he had a baby with another woman. Deep down it hurt me and I became cold with him and moved on. Fast forward a few years ago we reconnected. Both still single. We've been on many lunch dates, weekend dates, and sleepovers and I started falling for him again. He has expressed to me that he really likes me. He's an all around great guy, but we both have walls up. Making time for each other is difficult because he cares for his mother and my child is school age. We both work and have very good careers. We both are homeowners and just generally stay busy with our responsibilities so it can be difficult for us to make time for each other.
He went through a difficult divorce prior to me meeting him 22 years ago and I think that is what has his wall up. Me, I've just been duped so may times until I hold back, but he seems hesitant about defining what we are doing. He mentioned to me on a date once that I don't talk. I asked him to explain, but he didn't elaborate. So here's where I'm going with this question. You would think it would be fate that we reconnected the way we did, but it seems like we are back in the same place, not really knowing what we are trying to do. I recently thought about putting more effort into showing him how I feel about him. Should I or do you think it would be a waste of time? Is it fate or is it just the same old thing again? Is it time for me to let my walls down and believe this can work? Thank you for your time!
Thank you so much for writing in. Wow… There are so many layers to this. I have so many questions and only you have all the answers so before I give my two cents think about this. What is stopping you from going all in? You mentioned being duped, and him having a messy divorce, but when it is real you know it and nothing can stop you from going for it. You cannot allow your past to keep you from what might be a great present and future. Unless there is something you are not saying and you have a really good reason for not going all in.
You asked is it the same old thing, well is it? Are you two just meeting for the benefits or are you two sharing something real, building a future, connecting outside of the bedroom, actually dating? Typically, when two busy people make time to have what you describe as, "many lunch dates, weekend dates, and sleepovers", I would think they are into one another. The goal of doing these things is to fall, and stay in love right?
My advice… talk to him. Communication is key. Ask him what he wants and where he sees it going, and really listen to what he says. I am a firm believer in silence being an answer, so if he is not able to answer you that is your answer. If he has not thought about what he wants with you, or any future plans with you that is your answer. Trust your instinct, you are there with him. How does it feel? What does your brain say? You said he told you that you don’t talk. Why is that? What are you afraid of? What are you holding back and why? Is he hesitant about defining what the two of you are doing because you have a wall up? Like I said I have so many questions lol.
Hope this helps and gives you something to think about. If you want to talk more about this shoot me an email.