Dating at Midlife/widower


Hi, Azure,

I am 66 and have been divorced for 17 years. I have dated extensively over that period, including some relationships that lasted for a while. Most recently I was seriously involved with someone for 4 years and we even lived together for awhile, but that ended 5 years ago. I have met a number of men since but nothing serious has developed. I am at a point where I am pretty content with my life and not interested in settling for anything less than what I really want. Since the statistics at my age are not that great for women finding a partner, I am more or less resigned to living the rest of my life without a partner, although I still keep my eye out and am on several online dating sites.

My question is about a widower. I met him online back in Oct. We have a lot of things in common and he seems very nice. He lives about an hour away. He has been widowed for almost 4 years, but apparently has not done any dating. He explained up front that he is a little nervous about actually meeting someone. So we emailed almost daily for over 2 months. Not long emails, but just once a day, fairly short messages just talking about what was going on in our lives, esp. with our kids and grandchildren. Then after the holidays he took a group of students to Costa Rica for 10 days. He promised to write when he got back and tell me about the trip. Well, he never wrote back so I put him out of my mind. Then yesterday, feeling disappointed and frustrated, I sent him an email saying that it was unkind to write for 2 months and then just drop out of sight without a word. I got a response within a couple hours. Here it is:


You are right. I should have written, and thinking about it (which I did) does not countĖplus I promised Iíd fill you in on the trip and didn't. But I donít think itís been but a month and a bit, the first of January. After I returned from Costa Rica with my class, there was three weeks of nonstop work with the students up to this week when the new semester began. I thought about writing to tell you about it, but Iíve been having this internal fight with myself over this online dating stuff. Iím still having difficulty reconciling it with my life prior to Robinís death. I donít mind looking at Our Time, but Iím worried that I canít get past feeling guilty about it. This has nothing whatsoever to do with you. In fact, emailing has been good, and it has helped me. I just semi panic when I think of things beyond that. I think that Iím good on friendship. Iím not sure Iím good on things past that.

All of that said, I apologize for not having let you know that I was back or filling you in on the trip. Sometimes I become my own worst enemy. I hope you know that I love hearing about your grandson and all the things that you two do. While I may have done irreparable damage between us, I do hope not. I was not trying to be unkind, nor trying to ignore you. For whatever reason, I put off writing and then the days added up. Good intentions donít count, and I am sorry for that. I can only try to do better in the future if you would like.Ē

So my question is how to respond to this. I appreciate the fact that he has been open and honest about his internal struggles about dating. Iím not very familiar with widowers and I donít know if there is potential here and if he just needs more time or if Iím wasting my time on him. I donít know what the best course of action is. Just keep emailing like before and see if anything happens? Tell him I would like to meet him just on a casual basis for a cup of coffee and conversation, with no expectations? Write and say that we seem to have a lot in common, but tell him just to contact me when he feels he is emotionally available? Maybe meeting in person would make him feel more at ease - or maybe not.

I would appreciate your thoughts on this. Thanks in advance.

well, at 66, if your goal is to still find a special someone, there's no time for endless emails with no actual goal. the only reasonable choice is to offer up the suggestion of meeting (always with minimal expectation); if he declines, focus on looking elsewhere; if he agrees, then set it up for sooner than later; this is the ONLY way to appraise the potential of ANY dating relationship; certainly the in person dialog should include expressions as to what each of you is looking for--whether or not this results in a similarity of needs will determine, along with whether a mutual attraction exists, whether future encounters are plausible; but step 1, proactively move this along by ascertaining his interest in meeting...

Dating at Midlife

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can answer all inquiries relating to dating/relationships REGARDLESS of age or other factors, making the appropriate adjustments in thought/advice for each unique editor, "dating for dummies", dr joy browne..BA psychology, graduate study, fordham univ school of social work..


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