Dating a Widower

I have been spending time with a lovely man who lost his wife 15 months ago due to illness. He said they talked about his moving forward with his life. He is 61 and has a daughter who is 37, with whom he is close. She thinks that I’m going to take advantage of her father and take away the time he spends with her and her son, the only grandchild. When he tells her that he is lonely and wants to spend time with me, she makes him feel bad. He and I live one house down from each other and have coffee together every morning. I am divorced, with two grown children and five grandchildren. My friend wants his daughter to invite me to dinner and other events. I tell him that I understand that she needs time to work through the loss of her mother and the thought of her dad dating. He admires my patience. I’m wondering how I’ll feel when she gives her blessing for me to be around.

And I’m wondering whether she’ll grant your wish. You don’t say whether his daughter has a partner of her own, but that could influence her willingness to time-share her dad. There’s no finer tribute to a good relationship than loving again, but it may be some time before his daughter understands that. It’s her father’s place to help her know and accept that. Patience (yours) is great. But action (his) is better.

Why are you rooting for a relationship at the daughter’s bequest? Moving forward with one’s life requires that Mr. Widower establish the rules and boundaries of his own life—of course, with sensitivity to his daughter and the loss. That would suggest that he make clear to everyone what he wants and that he not prematurely push for you to be invited into his daughter’s home. First, your presence would be a constant reminder of the loss, apparently something she’s not ready for. But just as important: Is that really where you want to conduct most of your relationship?

If his daughter is accustomed to soaking up all her father’s time, perhaps he needs to wean her a bit. He ought to be making clear—very kindly—that some days or evenings are reserved for you. It should not be a matter of permission. He’s an adult, isn’t he? That arrangement would be most respectful of everyone’s needs—hers, yours, and his.

Grief Begets Regret

I am a year into the loss of my brother. We lived on separate coasts, and though we spoke, visited, and vacationed often, when he was diagnosed with stage-4 cancer, it was as if we were frozen in time. I can’t remember the details of our conversations, or even the level of emotion. It was as if it happened in a bubble belonging to others. What does stay with me is regret. Why didn’t I run out to see him when I heard or visit more often. Others remind me that I have a demanding business to run, or that I might have had a hard time believing it all, but these seem like unacceptable excuses.

Grief is a profound emotional experience, and yours seems to have started at the time you received the phone call. Anticipatory grief is a real thing. Like the grief that follows a loved one’s death, it stirs deep sadness, which slows us down and turns us inward so that we can understand what we most value about the dying person and begin adjusting to the loss by reorganizing the family of loved ones who live on in our heads.

Typically, too, sadness shares the psyche with sweet memories of experiences you two had together. It is natural for grief to stir up regret—remorse that you didn’t do more, say more, be more present: When you focus on the wonderful qualities of a loved one, you awaken the knowledge of what you value and want more of in your life. We come away a bit wiser, with knowledge of how to live our lives better or more faithfully to what we recognize is important.

Carrying that knowledge forward and putting it into action in your own life serves as a natural brake to guilt. The enduring remorse you’re experiencing suggests that you can’t find a way out.

Be kind to yourself. Allow yourself to understand what kept you from seeing your brother more often. Yes, a business to run. But perhaps you feared that the pain of seeing him dying would be overwhelming to you and harmful to your brother. Perhaps you were trying to protect one or both of you emotionally, but the finality of death enabled you to realize that, especially in the face of death, some things—like human contact—matter more.