How not to hit on a widow.


Opening day at the horse races in Del Mar, California always brings out the most interesting characters. There are big hats, tight dresses, and a plethora of plaid. I’m too much of a recluse to deal with people at the track, so I usually head straight to the after-party, which, in my case, should be called the during-party. I linger near the watering hole, waiting for prey. This year, I was taken aback.

“Are you single?”

“Yes. My husband died a few years ago.”

Most men, at this point, would show sympathy and offer the canned response: “I’m so sorry.” Not I. I took a deep sip of my gin-and-nothing, to ponder my response instead of blurting something I’d regret. I advise you, friend, to use the same strategy when asked your opinion–take the sip of consideration.

By examining my thought process, I’m convinced I need therapy.

  • Did she kill him? If so, how?
  • Did she hire someone to kill him? If so, was the hitman ever caught?
  • Is she done mourning yet?
  • Will this woman begin crying every time I do something that reminds her of the deceased?
  • Is she fucking with me?
  • Well, it sure beats needing to look over my shoulder for the ex who never leaves.
  • Does she have children or pets, and did the hubby take any of them with him into the ether?
  • Perhaps I should consult the Animal House dating manual, and review the chapter on Fawn Liebowitz and the kiln explosion.
  • Am I at the point in my not-getting-laid streak where I can take on this challenge and show sufficient concern and respect to break the streak, or should I slide my cards in and wait for a better set?
  • If she says he’s in a better place, I’m going to enter into a debate–one which rarely ends well for me.

I am not an insensitive prick. I’m a creative prick. Giving the usual response at the usual time is horribly boring. It’s far better to give the response nobody expects, and learn to become a better person by dealing with the aftermath.

She was very attractive, so I took a shot.

“You’re fucking with me, aren’t you?”


Her friend saw my train of thought heading into a wall, and offered her assistance, as the widow went to powder her nose.

“Actually, her husband did die a few years ago. He left her with three children.”

“Oh.” (Insert another huge gulp of gin sedative.)

“Yeah, she probably doesn’t want to talk about it. She’ll start crying.”

“Right. Well, in my defense, how was I to know? I was simply trying to discern her availability.”

“I understand.”

“If I were a beast, I would have said something like, ‘Did he leave you lots of money?'”

“He did.”

“I wasn’t asking. That doesn’t matter to me. I mean, good for her, right?”

“Good for her? She’s a single mother of three who lost the love of her life.”

“Aw, fuck. Sorry. Look, I’m not really this much of an asshole.”

“I’m sure.”

“It’s not every day I meet an attractive young widow.”

“Lucky for you.”

“Shit. Here she comes. I promise I won’t talk about it.”

I shifted immediately to small talk about living and loving in SoCal. Not much of a dancer, but I 23 skidoo’d and skedaddled, sadly, without her number.

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About the author

Author of humorous essays about relationships and lifestyles.