October 2020

Deciding Not to Settle: What I Learned from The Rules

Happy at the Beach. Finally done settling.

My absolutely best dating advice: Do Not Settle. 

But I had to figure that out for myself.  

Four years ago, I had a group of five girlfriends, all of us middle-aged, none of us happy with the men we were dating. Most of our guys (including mine) were unreasonably cheap. Several (including mine) complained about our alleged character defects while demanding way too much emotional labor. None of them were putting in much effort.

Yet we all hung in there longer than we should because, well, we hadn’t found anyone better, and going back to the dating sites sucked, and it was so exhausting to have to start all over again with someone new, assuming we even found anyone. 

We were all mired in lethargy. And we were all dissatisfied, and a bit angry. Was this all there was to dating at our age?

Why I Turned to The Rules

I have a confession. During my last round of dating in early 2018, I read The Rules. It’s a 1995 self-help book known for telling women how to catch a husband by being elusive, uncomplaining, and unrelentingly well put together.

When The Rules first came out, I was 32, a lawyer of seven years living with my high school sweetheart, later to become my husband. Back then, I thought the book was ridiculous. When you had true love, all you had to do was be yourself. 

But once I started dating after widowhood, The Rules began to make sense to me. I couldn’t take it literally, but The Rules were telling me that I had every right to expect a higher level of courtesy—dare I even say a dash of chivalry—in the men I dated. Which I’d been worried a Modern Woman wasn’t allowed to want. That deeply flawed book made me feel that I was not alone in rejecting modern dating, and modern men, as an exercise in apathy.

What was weird was that I needed this self-help book with its admittedly archaic ideas to tell me that I could want what I wanted. Back then I was caught up with wanting to seem trouble-free and low maintenance, open to almost anything, heh heh. I feared I was doomed to being alone if I didn’t lighten up.

As a naive, new widow, I hadn’t realized how much dating had changed since my high school days. Back then, the boy asked in advance and planned something you’d both enjoy. (Girls could do that too, we just didn’t back then). I still expected a nice man to ask me out on a reasonably planned date, open doors, offer a bite to eat or drink, and try to be good company. 

I did not get that.

What I did get was rants about exes, complaints about the cost of dating, and offers of second dates like just come over. Men wanted to see me, but they didn’t want relationships, hell, they couldn’t even manage to agree to an initial coffee date with a couple days notice. 

I worried that wanting a committed relationship was too old-fashioned. I hadn’t yet realized it’s better to be alone than to settle for the wrong person. Or that I limit my energies to finding the right one.

In the meantime, perhaps in deference to my age, instead of getting unsolicited dick pics, some men sent me pictures of themselves shirtless, sometimes photographed from behind, their pants or ill-chosen Speedos riding low enough to show off their butts.

Ass-first is no way to approach a relationship.

Is it Feeling Hostile in Here?

Photo by Alex Iby on Unsplash

Online dating has convinced me there’s a war going on between the single middle-aged daters. And it’s based on how much women will put up with.

The Rules say that if a man really wants to be with you, he will put some effort into spending time with you, pretty basic in theory, yet so rarely did it happen in dating purgatory. After a few messages, several men asked when I might be coming their way. A few suggested I meet them at their local watering holes. Some of them were miffed when I said I expected them to bridge the distance instead of my coming to them.

 A few messaged endlessly, saying they were too busy to meet, they’d let me know when they had time. Several mentioned a specific day to meet, but said they’d let me know the time and place on the day itself. These guys were like the friend you realize isn’t really your friend because they only make time to talk to you when they’re driving on their way to see other people.

I used to be on several Facebook sites for widowed people. I kept seeing posts from vulnerable young widows saying they’d met men who’d told them they were interested only in being friends with benefits. The widows thought the men would change after getting to know them better. Not surprisingly, the men did not change. The widows were heartbroken even though the men had been honest with them. They were just used to a world, as was I, where sex and love were partners. 

Cue The Rules which suggest you see what your date will offer when you don’t offer it first. If he doesn’t reach out to you, you have your answer. If his idea of a date is saying, ”I thought I’d stop by your place on my way home (from another gathering),” he isn’t offering much. If a person puts little effort into seeing you, they don’t care about you. No matter how much home-cooked food or awe-inspriring sex you provide. 

The Rules also advised keeping your private feelings to yourself until you really knew some one. You don’t want to pour your heart out to someone who turns out to be an unworthy receptacle. Better wait to see if his level of interest remains high for awhile instead of discovering he was just waiting for the metaphorical head push. 

And while terribly old-fashioned, The Rules advise holding off on becoming physical. Maybe it’s just me, but most of the men I’ve dated have changed after sex. Suddenly all effort ceased. I’d go from paragon to project. They’d wish I’d pay more, or be more nurturing, or more available. They thought I’d stick around simply because I’d said yes once before.

Had I held out, I might’ve seen they never saw me as a person–only as a vagina.

And sadly, The Rules also worked when I made myself unavailable to these men. They went back to asking when I was free, suggesting dates that required some thought, and again offering praise. But I still wished I’d waited because by then I knew they’d never really liked me in the first place.

It all felt like a power struggle.

An article in The New York Times suggested if you were to follow The Rules, you’d wind up married to a man you barely knew, someone strong of jaw and quiet of mouth with whom you’d never really been yourself. And that might be true. But they’re also saying not to give yourself to someone who isn’t invested in you. Be ready to walk away if you’re not getting what you want.

They were a tiny (albeit misdirected) beacon of hope in a world gone buttocks-up.

There is a Happy Ending

Just when I was about to succumb to excessive cat ownership, worried I was way too old-fashioned for this world, I met a man (story here) who seemed to have read The Rules himself. He called me for dates in advance, picked me up, turned down my offers to pay, and did not push for sex. He opened doors, pulled out chairs, and, most importantly, he said only kind things. 

But I’d needed to wait for him. And to keep searching. And, most importantly, to stop settling.

Hold out for what you want. Believe it’s what you deserve.

Deciding Not to Settle: What I Learned from The Rules2021-01-08T18:43:50+00:00

February 2018

Dating After Widowhood: You Can Withdraw Your Consent at Any Time



Consent for sex

Many of us are diving back into the dating pool after a long absence. It’s been many years since we’ve been romantic with someone other than our spouses. We might not know what feels okay until we’re actually on a date and things are becoming steamy. The most important thing we need to know is that we can withdraw our consent at any time. Even in the middle of things. No matter uncomfortable it feels to speak up.

We owe it to ourselves.

Our date may have done everything right; we’re just not ready to be with a new person. We thought wanted to get close, but when that started to happen, it didn’t feel right.

And that’s okay. You can’t tell beforehand how it feels to become intimate a new person.

But here’s the hard part: we’ve been trained to follow through once we’ve agreed to have sex. In the romance movies, the couple kisses passionately, then suddenly they’re stretched out in bed all post-sex and glowing. They don’t show the awkward stuff in between.

When I was in high school, my dad raised me not to let a boy pay for a date lest he seek physical reimbursement afterwards. According to my dad, all boys were after one thing and I needed to guard against it vigorously. He followed the old-fashioned model that once a guy got excited, he became a sex friend.  (In the eighties, one guy actually tried to convince my virginal friend that “blue balls” could damage him). So I had to do everything in my power not to excite a guy.

Many of us older daters weren’t brought up with the idea of consent. Like me, we were taught to fear the uncontrollable male sex urge. In middle-age, we believe that either you do or you don’t. And if you initially agree to have sex, you’re stuck.But you’re not. You can withdraw your consent at any time.

But if we want to end whatever’s going on, we need to speak up. A lack of enthusiasm or a grimace in a darkened room may not be enough to alert our partners that we’ve changed our minds. We need to say, without shame or embarrassment, “I need this to stop. I’m not comfortable with this.”

We might tend to rationalize, “It will be over soon” or “He’ll think I’m crazy for changing my mind.” But our bodies know. Even if our brains think we can go through with it, our bodies will feel betrayed. They feel at a level our rational minds may not. And a decent man wouldn’t want us to feel ambivalent or awkward about something so private.

Asking consent for each act

I’ve been reading about how Aziz Ansari chose to ignore his date’s signals that she didn’t want to sleep with him. I read an advice column where a man asked if he’d acted wrongly when his date told him after the fact she felt violated even though he’d truly thought she had acquiesced. We are reaching a new model for sexual consent. And it involves making sure beforehand that we and our partners are comfortable with each act of intimacy before it happens.

I know people think it can get silly when everything gets verbalized, i.e. “Can I touch your left breast? Can I touch the right one?” Or they think it’s not sexy. But I think it is (within reason). It shows our partners respect us and care that we’re comfortable. And in the time it takes to ask, we can decide what we want. Affirming consent as things progress changes the model of sex as “all or nothing.” It lets us change our minds as we go along. And it sends the message that there’s nothing wrong with that. It’s probably closer to how people really feel when they’re with a new partner, testing the waters before diving in.

In order to feel safe to try dating again, we need to be able to stop whatever’s happening if it feels wrong. At whatever stage. Even if we initially said “yes.” Even if our partners did nothing wrong. For no other reason than it doesn’t feel right. That is a huge reason. And we need to say it clearly without shame, “I need you to stop.”

Dating After Widowhood: You Can Withdraw Your Consent at Any Time2018-02-05T14:53:12+00:00

December 2017

A Widow Finds Love through Perseverance


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 Meetup.com).

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.



A Widow Finds Love through Perseverance2017-12-21T17:04:37+00:00
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