Dear Ann Cannon • I am a widow in my 60s and I’ve been dating for maybe nine years now. My past three relationships have had bizarre endings. Let’s start with the person I dated for four-and-a-half years. He stayed with me over Valentine’s Day and brought flowers, candy, jewelry and took me to dinner. The next morning I fixed a nice breakfast and he left — never to be seen or heard from again.

Let’s move on to the second Mr. Not Right. He called me every night and told me he loved me (I told him not to say that because I don’t fall in love easily). After no phone calls for two nights, I called him. He said, “I’ve been meaning to call you. Remember how I went to my class reunion? Well, something happened. I saw my high school sweetheart and we just hit it off.” The next day they announced their engagement on Facebook.

And now we come to the last Mr. Wrong. We dated for a year-and-a-half. He took me on trips and always brought goodies when he came to visit. He was always polite, but didn’t like to call me — he was a “texter.” So we got back from a trip (he even took his mother with us.) Everything appeared to be fine, but I didn’t hear anything from him in over a week other than some one-word texts. I tried calling after a week-and-a-half, but no answer. I texted and emailed because I was worried about him. I called his son and he said he had a text and that his father seemed fine. Pretty soon I got this two-line text: “I think we should go our separate ways. I wish you the best. Do not reply.”

So I’m asking you, Ann, have people just lost their minds, backbones and decency? Is it me? Is it too much to expect an explanation or a conversation? I don’t know if I dare trust any man again. I met these men on dating sites. Is this the wrong approach? I’m not a barfly and really don’t go places, other than meetups for dinner to meet people. Do you have an answer?

Disillusioned Dater

Dear Dater • Wow! I’m sure that if others had these experiences, they’d be disillusioned, too. (And for what it’s worth, I’m guessing there are plenty of men and women out there who have dating horror stories, as well.)

Like the song says, breaking up is hard to do. Always has been. Always will be. But I do think technology has made it easier for people to opt out of relationships without showing up in person. I don’t see things changing much on that front, unfortunately.

OK. Because I haven’t dated since I was 21 years old (and I was never very good at it anyway), I asked Facebook friends for their advice for a woman your age when it comes to dating. Their suggestions follow. (Be forewarned. Most of them involve you getting out of the house a lot more than you may be inclined to.)

  1. Volunteer. Even if you don’t meet somebody, you’re doing something worth doing.
  2. Go to church. RELAX, EVERYONE! It doesn’t have to be the Mormon church (though it can be!).
  3. Join more Meetup groups online and then — you know — get out and meet up!
  4. Several people mentioned friends who found significant others in grief support groups.
  5. Cook and invite people over to dinner. Tell them to bring friends.
  6. Move to Florida where there are more singles over 60 than there are here.
  7. If you do decide to try another dating site, have a friend you trust review your dating profile. Have your photograph taken by a professional or a super talented friend.
  8. Find a podcast or two that gives tips on dating for seniors.

One friend said, “STAY. SINGLE.” This made me laugh out loud, but I’ll leave that decision up to you. Best of luck!

Ann Cannon is The Tribune’s advice columnist. Got a question for Ann? Email her at or visit the Ask Ann Cannon page on Facebook.