This guy regrets dumping his mean, cougar sugar momma 25 years ago. Douche, or normal dude?


Of course he loved her.

Shelby Spires, 45, lives in Macon, Ga. He told me this story: 

I spent my career as a newspaper reporter and editor. I’ve done OK for myself — I own my house and car outright, I have enough investments that I can be picky about what kind of work projects I take. But there have been many times when I’ve found myself editing some crappy copy or changing a car tire, and I thought: “What would have happened if I married Naomi?”

When I was 19 I dated a 52-year-old widow. She was very attractive and dressed like she was 20. Naomi grew up with money and married money and was a successful real estate developer herself. I grew up middle class, and while I never really worried about having food on the table, it was thrilling to be courted with U2 concerts in Atlanta, sex and booze with what I considered a sophisticated older woman. That is what passed for erudite when you’re a teenage journalism student who grew up on James Bond novels.

But it wasn’t all glamour. One evening I was enjoying a Jim Beam in what was considered an upscale restaurant in Macon, Ga., (meaning they had linen napkins and a well dressed hostess) when Naomi literally cursed the waitress, calling her a “slant-eyed bitch.” It came out of nowhere. This was what first opened my eyes to her temper and racism. Aside from my literal drunk uncle, who had been shot up by the Japanese during World War II, I never heard racial slurs except on television or the movies.

But it wasn’t just how she treated other people. Naomi physically scared me. She’d grab me by the lapels of my jacket, throw me down on the couch, and say, “Fuck me!” Today I’d love that, but when I was 19 it was terrifying.

After a month or two she asked, “What do you want with your life? Where are you going? I want you to know that I’m here for you.” It was her way of putting the ball in my court, to let me know she wanted a serious relationship. Eventually I just let things drift apart.

I went on to marry and divorce twice – neither time to women with money. I sometimes think: If those relationships ended, why didn’t I marry and divorce and walk away with some cash? But then I work through the regret fantasy. If I had stayed with Naomi I would have wound up as some boy-toyed manager of a real estate company, become an asshole and got myself shot. Like I said – she was mean. We would have wound up in court – either criminal court or divorce court. She had money and connections and could have really come after me.

The regret pops up every now and again, but then I snap out of it after 5 minutes. If I had gone that route when I was so young I wouldn’t have pursued my career – written books and partied with astronauts and traveled all over the country. I wouldn’t have created the life I have for myself. To this day, I don’t really care for Jim Bean.

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11 thoughts on “This guy regrets dumping his mean, cougar sugar momma 25 years ago. Douche, or normal dude?

  1. If this was anyone but you posting this, I’d say this was fiction.

    But since you’re a straight shooter and you’re the one posting it, I have no choice to believe the story is true.

    To answer your question, he is not a DB…but he’s also not a normal dude.

    He’s not a d-bag because there’s nothing that can fix bat shit crazy. Which, if his account is to be believed, she was. He did the right thing by running for the hills.

    But he’s also not a normal dude because – how does one say this – I never once had the desire to do the deed with someone older than my mother when I was a teenager. And here I thought I was living dangerously by having an illicit love affair with a 21 year-old when I was 16…jeeezzz..

    1. Hi Harry- I always appreciate your comments. Yep, Shelby is a real person and a personal friend of mine. I disagree that he is ‘not normal’ (and not just because, again, we’re friends). I’ve dated all kinds of kooky people — some dating is for real partnership, some is for adventure. Not everyone is interested in the latter, so maybe that makes it hard to understand? I’m pretty libertarian about such things. And then I reach a point where I’ll judge the hell out of you.

  2. Emma – Thanks for your reply. I wouldn’t use the word libertarian to describe myself, but the stained glass does start to crack whenever I enter a church…Anyway, I think I can safely speak for regular dudes when I say this.

    If Shelby went on a campout with a bunch of guys, had a few beers along with everyone else, and laid this story on them…well, let’s just say Shelby wouldn’t be invited to the next campout. Women get creeped out alot easier than guys, but even guys have their limits.

    1. Harry…You must hang with some judgemental pricks! Most guys i know dont care. In fact, most guys understand how hard it is to meet someone and then also actually develop a relationship with them. Also there is the adventure aspect Emma mentioned. Most do not have that experience so they are pleased to listen

      1. I tend to agree with Jojo here …. As a single woman who often finds herself surrounded by married people I have seen that we are often the court jester, prodded for stories.

      2. @Jojo – There’s a world of difference between being 19 and, say, having a fling with a 32 y.o. MILF and being 19 and mooching off of Grandma.

        1. I don’t know … adventures are adventures. Why not? They dated, had a thing, he learned a lot and has some good stories. Where’s the harm?

  3. Growing up we were always told “It’s just as easy to fall in love with a rich person as it is with a poor person.” Tells you a bit about where I came from. :-)

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