Chapter 1

I was more than a little nervous, not having dated, let alone blindly, for a good while. I had mostly sworn off dating as a social convention, in fact, but out of sheer boredom or something, I had checked the dating site where I had an outdated profile and saw some matches. I had a little discretionary money at the moment and I was curious, so I paid to see who they were. One was a rather whiny, annoying woman closer to my own age, I basically ignored her. I didn’t need whiners in my life. They were bad vibes and all that jazz.

The next was a woman who was recently widowed and seemed a bit too fine with that. That fact alone gave me the creeps about her and I rejected her as well. She had “Black Widow” written all over her. I then saw the third match and liked what I saw, even if she was a bit younger than I went for in the past. Well, Simon, I told myself, going with women close to your own age hasn’t worked out so well for you so far, has it? I mean, sure for casual fun, that was great, but I had misgivings about what kind of relationship material they might be.

I had specific expectations and boundaries, and they were niche enough to be tough as it was. Most of the women my own age seemed to be desperate to claw their way onto a guy’s back, piggyback on him to an easier life, and keep him to themselves, even as they stepped out on him as much as they pleased. I didn’t want a cheating golddigger. I wanted honest polyamory, not secretive infidelity that kept me in the dark. Honestly, as this point, I didn’t actually hold out much hope that this would be anything but entertainment, even with the younger lady.

“I might as well go for it. At least I’ll be seen with a younger woman and that will probably fuck with Ashley’s head. She has it coming, too. That alone is worth spending a little money on a date,” I told myself.

I could have gone for a coffee date or insisted upon Dutch or whatever, but while I didn’t want golddiggers, I wanted word of mouth. Women these days, especially younger women, tended to blab about their dates, in this age of social media and influencers and all that jazz. I might as well exploit that for my own gain. It might not be technically a good financial investment, but I knew that I would derive some satisfaction from driving a further stake into the vanity and ego of my ex-wife and ex-girlfriends.

Oh, yes, I had some of those, too, both before and after my marriage. Not to mention during, but those were strictly revenge affairs. I had no desire to hurt those women who had helped console me during the aftermath of Ashley’s infidelity. I didn’t honestly think too much about my earlier girlfriends, especially since they were as old as me or close enough to it, not to mention as old as Ashley. I wouldn’t mind hurting some of the bitchy women whose masks had slipped when they got too cocky or whatever after my divorce.

Most of all, though, I wanted to make Ashley suffer, at least a little. She had it coming in spades. Funny joke, I thought then, given that she went through that “Queen of Spades” phase there. That rotten cunt needed a little further pain and suffering, didn’t she? She hadn’t nearly atoned enough for my taste. Okay, so maybe I wasn’t totally over her yet. I would be ... once she was in enough anguish, agony, etc. Going on even one date with a younger woman, even if she didn’t sleep with me, well, that would really hit Ashley where she hurt or lived or whatever idiom one wished to use.

I swiped right on the younger lady, who, to my surprise, almost immediately contacted me. My hackles were a little up, mostly out of worry that this might be a catfish scenario. Still, if she was a catfish, I would dangle the bait for her and see if she bit. She sent me three emojis, all hearts, and one word: Daddy.

Oh, God, I thought, she’s really playing up the age gap, isn’t she? Maybe she had issues or whatever. Well, that was another man’s concern in the future. Maybe she would be better off with an older man in that case. Maybe that would help her heal or something. Honestly, though, the younger generation overdid the therapy talk and picked at the old scabs more than was healthy in my own view.

I began my opening salvo by typing, “Well, I do have daughters. Three of them, in fact. No sons. I’m not sure how that worked out. I’d have to ask their mother.”

“Are any of your daughters married or are they all single?” the young lady replied with a wink emoji.

That was odd, I thought. Why would she ask questions about them? Maybe she wanted to hang out with them or something? Maybe she wanted to know if they knew anyone in common? I couldn’t be sure. Anyway, I sent a question mark emoji.

“Not married yet. I don’t know why. I’d have to ask them very awkward questions and it’s really their business until or unless someone wanted to introduce someone to me or whatever. If things got that serious, then I might have some input or perspective or wisdom to impart. The youth don’t tend to listen to their elders these days, if they ever did. I certainly didn’t as much as I should,” I replied laconically.

“Are you a single father, divorced, or a widower?” was the next query.

“Divorced. Once. I’ve had girlfriends, too. They just never worked out for me. Most were around my own age. This is a change for me, shopping in the junior section. I suppose that was because I traveled more in those circles and tended to meet women closer to my own age. It hasn’t panned out so far, as I said,” I messaged back.

“Just the one marriage? Hmm ... Just like my father. He divorced my mother some time back. It’s still a bit of an open wound. I hate how much both of them hurt ... and have hurt each other. Still, I have to confess that it was probably mostly Mom’s fault. She cheated first, at least. Then he cheated back. I can’t blame him too much for that. People make the mistake of thinking that Daddy is a pushover. They tend to push the envelope and then he shows them that he ain’t,” the young lady responded.