Dating divorced guy who is still in pain

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Dear Guys,

I have been seeing a guy who got divorced two years ago.  He went through a rough divorce and was betrayed pretty horribly by his ex. They have no kids and have had no contact in nearly the two years since all has been finalized.

Last weekend I stayed at his place for the first time and during that time he started to show me pictures on his computer because he has an online business and wanted me to see his commercials. In the process he came across pictures that set him off. He spent the rest of our time together over the weekend telling me the divorce story over and over. The pain I witnessed was horrible. Not only did I learn more than I wanted to ever know but he made statements about how the future is lost, how he had planned a life that will never happen, that he doesn’t know what was true and what was a lie. He would mention little things they did together.  That they had so much fun and it is gone. I felt like I wanted to be supportive and understanding but at the same time I felt like he was dismissing any opportunity that we could ever have—that he is so deep in pain still that perhaps there isn’t room for me or a future. This is all new for me. I have not dated someone divorced before.

I don’t know if I should feel complimented that he trusted me enough to let me in to his darkest thoughts or if I am hurt over his talk of dispair and hopelessness over prospects and a future lost. I’m a patient person and willing to take a risk but I also don’t want to be played a fool. I left exhausted and cried the whole drive home. He didn’t communicate with me today at all. Something we have been good at and consistently have done since our first date, even if only a hello on text.

I need advice on where this guy’s head is at and what I should be doing.

Hang in there or move forward?


Dear Mic,

Thanks for your question.

Clearly this guy has a lot of healing still to do. And based on how intense his feelings are, it might be quite awhile before he’s able to be truly open to a new relationship.

Obviously he feels very comfortable with you, otherwise he wouldn’t have opened up to you so much. We don’t think he’s playing you or using you, but if you’re willing to listen, he’s going to talk about his divorce. In fact, he’ll talk to anyone willing to listen because his feelings are still very raw. Sure, this is understandable, with all that he’s gone through—and still going through—but do you really want to be his main sounding board? You need to ask yourself that very question, because this is unlikely to abate anytime soon.

If you’re up for the challenge, and you believe you have a very strong connection with this guy, proceed with caution and patience. But understand you will be challenged on many levels if you stay the course. It’s up to you to decide what’s best for you.

Good luck,


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2 Comments on Dating divorced guy who is still in pain

  1. Thank you Guys for your advice about the Divorced Guy in Pain. Since I first wrote you he has continued to degrade. I asked him to seek professional help. He agreed to do this and in the process I set up some boundaries in order to protect myself. Things worked for a short time but then he blew and started to accuse me of saying and doing things his ex had done for no reason at all. He became extremely paranoid and frankly, ugly. Out of the blue he lost it. I pleaded with him to get professional help and to please take himself off the market until he is ready to really be healed and ready to be fully with a new person and not living in the past.

    I am sad that he is so hurt and that things ended so poorly but feel I did nothing wrong other than to be supportive. I only hope he can heal since he has some wonderful qualities and gifts.

    Thanks again for the advice. Peace and Love to you.


  2. @Mic……thanks for the update. We’re sorry things didn’t work out. And yes, we hope he gets the help he needs. And of course, we wish you the best. Enjoy
    your fourth of July weekend. Take care.

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