Gay guys.Decision of my life. How to make this first move with closeted men?

My first thought would be to strike up a conversation about something you both have in common, e.g. what's up with the catholic church and their out of date beliefs re abortions/gays. You could talk about your mutual divorces, what went wrong etc. My second thought would be to get him drunk and explore that. It's not the best option however, because folks should be more honest about themselves, but sometimes a little deception works too.

 

Forgot to mention - I held an executive position for over 20 years. I behaved as a straight, married guy. If somebody picked up that I was gay (it did happen once) I would shut them down. There was no way I was coming out at work. Nor would I explore a gay relation with anyone from work, outside of work. That would never happen. You are going to need to find a safer place to bring him out, away from work, so there is no way it could get back to anyone at work.

 

I was out before getting married. I was also struggling to find a job who would keep a gay guy employed. I met my wife-to be at work. She was older, tired of dating and wanted a child. I also thought it would be great to have a child, but I knew that as a single/gay that wasn't going to happen. My wife knew I was gay, and we agreed to get married, hopefully I would be able to produce a child (I was) and we would stay together for the 20-25 year experience. After said offspring had grown up and moved out, we would either amicably separate or stay together, depending on whether we wanted to be together at that point in our lives. I got hired to my corporate job less than 30 days after getting married. I learned from this that as long as you are straight, you are employable. It helped that the corporate controller was my wife's brother-in-law. It's amazing how the straight world works. Anyway, I was now living a straight life, and had no desire to change that. Thirty some years later, my wife simply moved out. She was done with me. I was surprised as it happened with no prior notice or discussion. I guess I always knew it could end this way, but she could have at least talked about it.
I had an employee who picked up I was gay and tried to instigate a "bathroom quickie" with me at work. You've got to be kidding! He was cute, but I had a career and family that had to come first. There was no way I would do something so stupid at work. Whatever you do, it has to be separate from work, and not get back to folks at work.

 

Neither. You don't know that he's the love of your life. Do you? And don't get him drunk to change what should happen in a sober state. In 18 months, nothing has happened? No hints? Brushing of the arms? If you like each other, keep hanging out. Time will wear away at the obstacles, I think. Have you gone places together alone?

Why is he so fragile and fearful? Of what and why? It sounds like you are the more assertive one of the two.

I think this pretend thing happens a lot when there is a lot at stake and certain types of upbringing. Don't feel bad about that. I think it comes with the territory.

It would be helpful to get more insight into you and him and how your approaches might differ.

 

Both those ideas will most likely not go well.
If you give out some subtle clues about your own orientation he will pick up on it ... at his own speed

 

I guess I have a distorted point of view - I don't see her leaving me as punishment, I am free now. Nobody can take away my memories of family that I have.

 

I actually wonder if it might be better to write him a carefully written note, rather than confront him with your feelings and place him in the position of responding immediately. If there is a lot of tension between the two of you it might not be helped by surprising him with a sudden and unexpected declaration of love. By leaving him a note that you have taken time to write, you give him time and space to consider things carefully and soberly (getting him drunk and making a move is a bad idea).

Of course there is no guarantee that he will acknowledge his feelings, even if you do send him a note, but nor will he be able to ignore them once you've put it out there how you feel.

What do you think?

 

I’m curious, do you feel like you missed out on anything all those years with your wife? Effectively being in the closet? Did anything happen with other men while you were married? Does your kid know now? You don’t sound as though you regret it...

 

-> I’m curious, do you feel like you missed out on anything all those years with your wife?

Not off the top of my head. It's like taking a vacation to Hawaii and regretting you didn't go instead to Florida. Instead of regretting, I enjoyed the trip I was taking. We had so many family-type events, family christmas, mother's day with mother-in-law, etc. All decent experiences I would not have had gay/single. I sometimes wondered if I had not married if I would have ended up dead from HIV/AIDS? We make decisions in life, and I was enjoying my side route no matter what. It would have been harder to have stayed in a gay lifestyle, as the world clearly does not like gays.

-> Did anything happen with other men while you were married?

I had two occasions across 36 years where I was caught out, and approached. In both cases, I shut the other guy down. I was married, and not willing to risk my straight-life for a fling. I proved this many times to my wife by letting her clear my voicemails for me. On a busy day, I could get 50-60 voicemails that needed to be harvested and responded to. That would take me hours. I would give my phone to my wife and she would go through them for me, making notes on which ones needed calls back. She knew I was clean with her - nothing hidden.

-> Does your kid know now?

Not sure. About 4-5 years ago, my son came over to where wife and I were living. The first words out of his mouth were not "Hi mom/dad" instead his first words were directed to me where he said "I don't like how you are treating mom." I gave him a sideways look, turned around and looked at my wife and asked her "What the hell is he talking about?" She got a strange (I've been busted) look on her face. She said she would fix it. So three years ago, my wife moves out, apparently my son helped her do so, as he ripped off some work parts/equipment that only he would have known about. I have not heard from either my wife or son for the past three years. He's a adult, so gets credit and blame for his actions. What am I supposed to do if neither wants anything to do with me? Son and I never discussed dad's history prior to mom, so I truly don't know what she has told him.

-> You don’t sound as though you regret it...

I have no regrets. To know me is to love me. I no longer have any interest or energy for beating myself up over anything. I'm a decent/good person. I'm not perfect, and don't pretend to be. Regret drags you down. It's just not where I like going. I don't feel our marriage was a total failure. We both had a kid and all the family stuff that comes with that. Nobody can ever take that away from me. My son had a good, nurturing upbringing, with two parents who loved him a bunch. He knows that, regardless of what he thinks of me at this time.

Everybody needs to get on with their lives. I'm certainly doing just that. I'm truly free now to pursue my dreams.

 

Maybe a different approach - ask him what his greatest fears are? That should make for an interesting conversation.

 

There really is this thing called "seduction." Stop negotiating the relationship and start greeting him at the door in a pink Speedo with a tray of martinis. Have one of those gay self hypnosis playing with the sound all the way up. Stop thinking "we shouldn't be doing this" and start thinking "How tight are those jeans, anyway?"