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?

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.