Several days after meeting a man and getting his phone number, I found out that his girlfriend had passed away about a month or so prior to our meeting. We dated, and I noticed at times that he would withdraw/shut down, but I didn't know what was going on. It was a little frustrating, but now I understand that he was grieving. At one time I did ask him if he felt guilty because of the feelings he has for me. And his answer was yes. Our relationship has slowed down, but we still talk, flirt with one another, and go to lunch. There has been no real intimacy for about 4 months between the two of us, but we both still have feelings for one another. I don't know if I should move on, because I feel like I need more from him, or should I wait for him to grieve? I am in love him. I have my own issues because I am divorced and still transitioning from that as well. So the slow-down was okay with me. I know grieving is a different process for everyone, but how long do I wait?
Your question contains a few hints about what's going on and what you could do. It sounds as though there are some gaps between you and your friend. Apparently he wasn't forthcoming about an important event in his life—the death of his girlfriend. And you seem content to do a lot of waiting. Yet you, too, have something of substance to talk about—your divorce. I know that you probably don't want to base your relationship on death and divorce, but you could include these central issues in your conversation. If these powerful matters are there between you, why not talk them through together? There is a lot of life to be lived between you, but you could give the past some attention without overdoing it. The honesty and openness of the conversation could give your relationship a solid grounding.
The other gap is your waiting. Most of us wait for the other person to make a move. But this relationship is clearly something you want, so you may have to take the initiative. Waiting can be a passive, masochistic thing. You suffer it. The more you wait, the worse it gets. But waiting, too, can be done in small doses. You've already waited. Now take a cue from your impatience and do something.
It is possible to be too sensitive to another person in a time of grief. You may sentimentalize the grief. Outside, you try to be patient and understanding, while inside, you're boiling for some action. This is like yin and yang. You need both, and in this case the yang side—the active, impatient, initiating part—may need to come to the foreground.
I suggest having a heart-to-heart talk. Tell him you know he is grieving a loss, but you want to go on with life. Tell him you are also still struggling with your divorce, but you definitely want to get on with life. You can share your grief, and then share some life.
Tell him you’ve been waiting for his grief to tone down, but you’ve waited long enough. You don’t have to give an ultimatum, but only encourage him to find vitality with you. I think that if he knows that you are aware of his grief and that you understand it because of your own feelings about your divorce, he may have the common ground he needs to set aside the intrusive quality of his grief.
If not, he is hanging onto his suffering excessively, and you may have to go on with your own life until, perhaps, he understands. You know when you have waited too long. Know also that waiting can become masochistic, which means that it is fruitless and battering.
In short, you do two things at once: you acknowledge the grief you both have, knowing that it will never completely end, and you acknowledge your desire to start life afresh. One of the great strengths of human beings is that they can do two things at once, without having to make sense of it all.