My Instagram Post with tags “#SecondChapter” and “#InLove”: What mushy optimist posted this drivel?

I recently got an email from a widow of fourteen months who asked if it’s okay to fall in love again?

Hell yes! We deserve love and we deserve to be in love. I wrote about that here.

I just didn’t think it was possible for single people over forty. We carry too much baggage. We’re too idiosyncratic, too entrenched in our ways. We don’t want to disrupt our lives. We want our meals and our rooms just so. Our schedules are sancrosanct.

But then, I found my person. Actually, he found me.

In  September, I was again trolling through my OK Cupidity messages when I got one that said, “We’re both culturally Jewish, nonreligious lawyers who are looking for a relationship. We live ten minutes apart. Do you want to talk?”

”Sure,” I typed back. He turned out to be awesome. He still is.

I’m no longer a cynic. And I may be out of weird dating stories. (Almost). But not advice.

I wish I could say I did something miraculous to find my guy, but I just hung in there, staying online (I even tried Coffee Meets Bagel), answering messages, going on dates with promising people, and smiling so much I thought I had fishhooks embedded in the corners of my mouth.

I hung in there even when I didn’t believe the right person even existed. Prior to meeting my boyfriend (who I hope isn’t reading this) I was dating a polyamorous doctor with a Wharton MBA who’d abandoned both medicine and business to become a tantric sex instructor. I didn’t see it as forever–more like a weird field trip—but at least it was interesting while I kept up my search.

The best dating advice I’ve received:

There’s a reason all these people are single.

But there are good guys out there. The men who’ve commented on this very blog have been thoughtful and perceptive even when I’m verging on man-bashing. I joined a hiking group on Saturday mornings and there were several articulate, nice, apparently available, guys, including a few widowers who described their losses with real depth. (It’s the Hike On! group in

So, my very best piece of dating advice:

You are going to want to I've up. Don't


If I’d given up when I was getting sick of the process, when I was getting messages from the disturbed, when I was sick of rejecting and being rejected, I never would have met my current boyfriend. And once I met him, even on our first date, I knew I was done. (I even agreed to dinner instead of coffee for a first date).

My second best piece of advice:

Do Not Settle for Less than You Deserve.

I learned this the hard way after dating the emotionally abusive guy I’ve talked about here.  I wasted a lot of time dating guys I was never going to have a future with. (Being a writer, I could call it research). George was my high school sweetheart, my one and only. For a while I was looking to have experiences since I never had them when I was younger. But later this year, I wanted to be in a long-term relationship.

What helped me to figure out what I truly wanted was making list of the qualities I sought in a man. My friends had said to do this, but I ignored them.  It wouldn’t change who I met. But it did change how I filtered people out.  Here’s my list:

Debbie’s Guy:

  1. Can be a grown up if necessary
  2. Gets my sense of humor
  3. Good with time apart
  4.  Wants to travel
  5. Socially appropriate and articulate
  6. Non-workaholic
  7. Emotionally available and affectionate
  8. Quiet about former partners
  9. Positive outlook
  10. Financially stable

The list grounded me when I got caught up in messaging with someone who wasn’t right for me. I just think a guy over fifty shouldn’t be living in his adult kid’s basement. Even if he is really cute.

So now, I’m trying to be more positive. I’ve stopped prefacing all my sentences to my new boyfriend about the future with “If we don’t break up by then.” Then he can stop prefacing his future plans to me with, “Stop being so negative.”

I feel a sense of possibility. I even cleared out my spare room of all the excercise equipment I no longer use. So, now it looks like this, empty and open to something new:

Debbie's Empty exercise room with Billy Idol poster
My Empty Room

So that’s what I want for all of us this season: a sense of possibility and expansiveness, in all areas of our lives. Tell me what you want for the new year, or ask me your dating questions. (Hell, ask me anything, it’s lonely being a writer), in the comments below.



P.S. I was so surprised and grateful that Feedspot listed my blog in this list of top 50 blogs for widowed people.



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