Good advice for dating old
(No. 81) Introducing a new dating column in Stephen's People. by Stephen (still single) Williams
Two Old Bitches told me today I should write a dating column in Stephen’s People, giving insights into the male dating mind. Specifically, the mind of a male of a certain age. So that’s what I’m gonna do.
I’ve been divorced twice. (All my fault, both times. Or so I was told.) Since my last divorce 12 years ago I’ve dated a few dozen people. Usually it’s been one date. Sometimes it’s been three. Only rarely has a relationship gone beyond that. The longest, with a wonderful woman who I still revere, lasted about one year, ending right as the pandemic began. These experiences, and 25 years of therapy, are all the expertise I have. So take my advice at your own romantic peril.
While I’d love for you all, men and women, to send me dating and romance questions (I’ll even advise you on marriage, if you trust my thinking on that matter), in this first column I’ll offer my own tips, to women seeking men, about online dating profiles.
Some of its gonna be harsh. So steel yourself. But I think I’m gonna help you get more dates, no matter your age.
Photo fails
From my experience, the biggest turnoffs in online profiles of middle aged and older (45 and up) women are:
Fish.
This can’t be stated too forcefully. Do not post photos of yourself holding up big, slimy fish while squinting into the sun in a silly tourist trap t-shirt. First, these photos pander to stereotypes of men as fishing fools (some of us prefer big game hunting). And second, it forever associates your face with a scaly, dying animal.
Yoga poses
I respect that you flew to Costa Rica to get more in touch with your practice. But I don’t want to see photos of you twisted like a pretzel in sweaty, revealing Lululemon gear. TMI.
Slasher effects
Posting group shots where you have scratched out the faces of the other people (often your ex) suggests “serial killer.”
Scenery
Posting more than one photo of the mountains or desert or whatever place you once visited is a definite no no. I’m not going to be dating your vacation spots. I’m going to be dating you.
Avoid listing your deal breakers
Many women open their profiles with a list of red lines that must not be crossed:
No beards
No flakes
No debt
No texters
No one-night-stands
No FWB
No smokers
No cat allergies
No dogs
No kids
No exes
No fun.
Actually, that last one is just what a suspect a date with a negative list maker would be like. While some would view this is a straightforward way to get what you want, to me these lists say “I want to control your life.” No thanks.
Requirements
Often, women will post a list of desired qualities (like the above list, only in reverse). These include:
Must be my partner in crime.
This is so cringe. I can barely write the words, “partner in crime,” without barfing. You want me to take the fall for you when you rob a bank so we can afford to spend the weekend at an upstate farmhouse? Or do you just want us to pretend like we’re outlaws, our love against the world? Either way, I’m not gonna be anyone’s partner in crime.
Must be trim, because we all know that being overweight reveals a lot about a person’s mind and character.
I’ve read this actual sentence. This level of judgmental neediness is terrifying to me, even when I’m at my thinnest.
Must love cats.
I’d rather be with a woman who’d get rid of her cats to be with me.
Must be financially secure.
Ok, this one throws me every time. I live in New York City, where “financially secure” means everything from having a 40 million dollar apartment in the clouds to earning $18 dollars an hour on the side while you do your art. But I figure I will always fail this requirement, so time to swipe left.
While my track record of divorce and being single most of the time would seem to preclude me from offering dating advice, who is to judge? Ha ha. Not me. Send me dating questions at stephen@stephenpwilliams.com. or post in the comments section.
