Worlds Collide [Dating Story]

[Names and some other specifics changed to protect identities.]

Some time ago I met a man on a dating site. Let’s call him Walter. He was a teacher. We chatted on the phone, made a plan to meet at a local cafe, yada. I was pleasantly surprised to discover in person that he was a nice-looking guy who seemed smart, funny, etc. Then he looked out the window and said, “Hey, there’s my roommate!”

I saw an elderly lady walking slowly down the sidewalk. “Her?”

“Yeah, the old lady!” Walter laughed. “A couple years ago I answered her ad for a roomie because I didn’t have much money after my divorce. We hit it off and have been together ever since. This is our second apartment together.”

“Oo-kay.” The woman was probably around 80; Walter was my age, around 50. “Doesn’t that interfere with your social life?”

“Nah. We have our own rooms and bathrooms. Sometimes when I have a date we all watch TV together in the living room. It’s totally cool.”

Walter and I hung out for a while longer and I asked him why he broke up with his last girlfriend. “Skyler was a wealthy divorcee,” he told me. “Traveled a lot and played golf all day, but I had to work. Eventually she got really clingy and wanted me to move into her house.”

“But that seems ideal,” I said. “Or… didn’t you want to leave your roommate?”

He shrugged. “I like my life the way it is.”

Walter asked me out again, but his sitch with the roomie was just too weird and I declined. I didn’t understand what was going on there, plus Walter didn’t seem like he wanted any kind of serious relationship in the near future. I don’t like to date just to date. End of.

Around six months later I met a new man on a different dating site. Let’s call him Hank. I really liked this dude. We chatted, made plans, yada. In person, he was even better. Very smart, very funny. I had high hopes for this. We went to a nice sushi place for our first meeting, not a boring coffee date. It was all going really well, I thought. Then I asked him one of my standard questions: what happened with your last girlfriend.

“She was a wealthy divorcee,” Hank said. “Traveled a lot and played golf all day. That’s not really my lifestyle. We were together only a couple months.”

“That’s funny,” I said. “A guy I met a while back said the exact same thing. And she asked him to move in.”

“So did Skyler.”

“Oh, my God! It’s the same person!”

Hank stared at me. “The teacher who was living with the old lady?”

“She told you about him?”

“Yup. He was really weird.”

“Haha, I thought he was too. I only met him the once.” The conversation was so odd. Hank had dated, for a couple months, the woman that Walter had been with for a while. It was so bizarre that I’d picked both of them out of dating sites. Did they have a common quality that attracted Skyler and me, or was it all a logistical coincidence of ages and locations? I felt very awkward and uncomfortable for a few minutes, pondering this while keeping up normal chitchat.

But the rest of our date went fine, I thought. No problems. I had a good time. Hank seemed to as well. We hugged and said we’d stay in touch. And we did, a little. But he never asked me out again.

Time passed. Finally I emailed Hank and said hello bla bla and hey why hadn’t we gotten together again?

Hank said that was a good question and it deserved a thoughtful answer.

But I never received one. Or any answer at all.

The end.

19 responses to “Worlds Collide [Dating Story]

  1. LOL – you’re amazing. There’s a Bridget Jonesian movie in your life.

    Liked by 1 person

  2. My oldest son was born in 1961 (deceased), so because of your age and sweet spirit I feel motherly advice coming on. (Pause.) There. I suppressed it. But I’m with Toon. You’ve got chick flick in your future.

    Liked by 1 person

  3. You should totally date the wealthy divorcee.

    Liked by 2 people

  4. Erase profile and start with a new site. Eww.

    Liked by 1 person

  5. Maybe you and Skyler could hit it off and you could become her kept roomie.

    Liked by 2 people

  6. Haha, if only we knew who Skyler actually was… I could see cozying up to her. 😉

    These stories are far in the past. That’s why I think it’s safe to tell them, with some deets changed.


  7. OMG, that is so bizarre. Also loving the “Breaking Bad” pseudonyms.

    Liked by 1 person

  8. So Skyler asked Walter to move in with her, but later also said he was weird. She also asked Hank to move in with her. Sounds to me like Hank was the only one who wasn’t weird.

    Liked by 1 person

    • Yah, at least according to these two dudes, she did seem a bit desperate for a live-in guy. With all the mooches around, it’s hard to believe she couldn’t find someone to move in with her and take advantage. I’m sure she has by now.


  9. Excellent poast! What strikes me is this. If Walter likes his life the way it is, why is he even dating?

    Liked by 1 person

    • Thanks! Well… a lot of older people seem to want someone to smoothly mesh with their life without having to make any changes. They don’t want to disrupt their existing routines and they don’t want to cohabitate. I’m sort of like this myself, which is one of the reasons I hardly date at all these days.


  10. This post needs a sound track.

    So, Hank and Walter each dated two of the other’s dating choices, so they must be alike sort of? Do you and Skyler have a common quality? Do either of you have a common quality with the old lady roommate? Will Hank get his much needed brain surgery, and will he ever find out that Walter is his half-brother, or that Walter’s roommate is actually Barbara Bush who was separated from her entourage last fall?

    Liked by 1 person

    • Dark Side of the Moon? 😀

      Walter and Hank were both funny and slightly cool/reserved. I find that emotionally distant quality attractive, as opposed to the guy who blabbers out every honest yucky feeling right off the bat as if he can’t control himself ever. I want to think that I have to work a bit to discover the interesting, deep, real dude underneath the cool, witty exterior bla bla bla. And that I will be special for getting to know that inner guy whom others don’t get to see. I like to see that a man has his life together and his emotions under control. Of course, it always ends up being an illusion and a pile of lies. Either he falls apart into an even worse pile of yuck than the immediate blabberer or he’s a con man.


  11. FIrst, I just opened with “so,” but . . . it seems different there.

    Well… a lot of older people seem to want someone to smoothly mesh with their life without having to make any changes. They don’t want to disrupt their existing routines and they don’t want to cohabitate.

    This sounds like wisdom. Only the degree of smoothness in the mesh, and the percentage of routine vs change varies with age and/or energy level.

    Liked by 1 person

    • Yes. I see my 20-something daughters and their boyfriends full of energy and compromises, eager to start lives and make plans. Peeps in their 50s? No way. They need someone who can fit seamlessly into a life already there. If you can find that person AND be mutually attracted AND love dogs AND have the right amount of money AND bla bla bla bla? Better odds playing the lottery.


  12. Wow. That is a good story.

    Liked by 1 person

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