06/21/2011 10:29 am ET Updated Aug 21, 2011

Remedial Dating for Middle-Aged Men

When a colleague and I want to vent but don't want to admit we're complaining, we call it "marveling."

So please let me marvel for a moment at five disappointing first dates after more than two years of hibernation as a young(ish) widow. They included well-intentioned fix-ups with an egocentric artist, a producer of a sleazy reality show and a crunchy stay-at-home dad, and ranged from the merely awkward to the downright offensive.

"I know I'm smart, attractive and successful," one well-groomed suitor told me. "It's just hard to find someone who meets my standards."

Seems to me these men, aged 46 to 57, could use a few pointers, and after two happy decades away from the dating game, I have the fresh perspective required to enlighten them. Here are some lessons from true forays into the uncomfortable world of meeting for that very first drink.

Don't tell me your therapist calls you "a catch." Let me decide for myself.

Don't disparage your ex-wife within five minutes of introducing yourself.

Don't tell me she was abused by her father either. Besides violating her privacy, it has to make me wonder what you might tell someone else about me.

Ask follow-up questions. If I tell you I've poured my heart into writing a book, don't change the subject. If you have zero curiosity about what makes me tick, this is hopeless.

Let's not make dates by text message. We're grownups. Pick up the phone.

If you're a widower, let's not spend our entire hour together talking about your late wife. I understand the impulse -- I miss my late husband terribly, and frankly, wish to the deepest reaches of my soul that he could be the one sitting here, ordering me a Pinot Grigio, instead of you. But I can't have him back, this is a harsh world to face alone, and I'm looking for a little fun companionship. It's natural, even honorable, that we bring up our beloved lost spouses from time to time, but let's not obsess. If we can't find anything else to talk about, that's not a good sign.

Let's not get scatological either. Consider this encounter with a child psychiatrist from an Ivy League school whose credentials might suggest decorum. When I mentioned something about texting, he launched into his fascination with a web site that collects examples of mistakes made by that gizmo that tries to anticipate the word you're typing. He gushed with delight over its prediction for "big shirts" (think bathroom graffiti) and "Virginia" (as in female anatomy). Call me a prude, but I don't think they're appropriate topics for an introductory conversation.

If you want to meet someone online, here are a few tips from my one disastrous week in that time suck (which apparently works for many people, but wasn't for me). Avoid cheesy screen names like "CaptainRomance," "JerseyMensch'' and "Lukin4Luv." Please be aware that you'll likely get deleted if you can't spell or capitalize, wear a wife-beater or no shirt at all in your picture (ugh), post more than 10 photos (vain), or use a portrait where it's clear you have simply snipped out your ex (her blond curls still poke into the frame).

To be sure, I've got plenty to learn myself. After doing a full public records check on one guy before we met, just to make sure he wasn't a serial killer, I probably shouldn't have mentioned it. "So, how'd you get those two speeding tickets?" was not the most fetching icebreaker. Neither was my query about his $46,000 income tax debt. Or the secret kids he left behind in California...

When I was young, my mother's only dating advice was simple: "If you talk about him all night, he'll have a wonderful time." Maybe, but you can easily wind up with a narcissist. There must be a middle ground somewhere, a place where two people with kindness and integrity can learn about each other and find some kind of connection.

It's just probably not going to happen with the man who told me, on a first date, that I ought to see a shrink. I'd rather call my colleague to marvel.