Courting Disaster is Jackalope Ranch's weekly column of dating horror stories, observations, how-tos, and more by Katie Johnson. Names of ex-boyfriends, past hookups, and bad blind dates have been changed to protect the guilty.
For as many guys out there fantasizing about having a threesome, there are just as many women wanting to, at least once, date an older man.
See also: 10 Phoenix Guys You've Probably Dated
Like the threesome, there is some fine print. Just as the men would prefer a threesome with a higher female-to-male ratio, women ideally would prefer that their older love interest not resemble the Cryptkeeper and be somewhat successful, well-off even. Because when a guy your own age can't get his shit together, it's annoying, but when he's older than you, it's just sad. Don't believe me? Go visit my father.
I was able to check "date an older man" off my sexual bucket list over the summer when I was 25 and met a 42-year-old man we'll call "The Neurologist." One, because I won't say his real name; two, because that was his actual job; and three, because it makes him sound a lot smarter than he actually was.
We dated for a couple months, and during that time I ate at some of the most expensive restaurants, was offered plane tickets and designer purses, and encountered some of the strangest sex of my life.
Perhaps "strange" isn't the right word to describe it, but what do you call it when you notice that a guy has been watching his reflection the whole time you've been messing around? Lame? Narcissistic? I'll go ahead and call it flashing red sign number 238.
Side note: When you go over to a man's place and notice that his bedroom is covered in mirrors, just make a mental note that shit's definitely going to get weird.
Also, I say flashing sign number 238 because, as sad as I am to admit it, I had picked up on many: the heavy drinking, the man jewelry, the weird relationship with the mother, the strong metrosexual tendencies, the rollerblading, the inability to remember even the most basic details about me, his propensity for estrogen-infused cocktails (appletinis, cosmopolitans, etc.), and naming his heavily accessorized chihuahuas after rappers (the black one was Snoop Lion and the white one was Slim Shady... yeah).
But the final breaking point happened during a Gypsy Kings concert at Talking Stick Resort (because remember, this is a story about a sad middle-aged man). He kicked off the evening with his usual swagger: excessive drinking, thick black-frame specs, and an ensemble that made him look like Brad Goreski from It's a Brad, Brad World.
We stopped to pick up his friends on the way, and he insisted on pounding down a few more drinks before showing us all how fast his limited-edition sport car could go from 0 to 100 mph on residential streets and the Loop 101. It was a high-speed douche beacon just asking to be pulled over by the cops, yet somehow we made it to the casino, unscathed (relatively).
We never really got to enjoy the concert. When he found out that I had arranged other means of getting home because, you know, I didn't feel like dying that night, he took a few more bracing shots of whatever ovarian cocktail he was drinking and proceeded to tell me that I had better learn to change because he sure as hell was not. If I wanted these nice material things he was offering, I need to act a certain way. I needed to maintain my looks, not gain weight, and seriously make an effort to control my lazy eye (as the Flight of the Conchords would say, "Wear the eyepatch, Bret. Wear the funky eyepatch.")
I must say, the one nice thing about crying in public at a casino is that even with your makeup smeared and your face flushed, you'll look around and realize you're still not the saddest person there. Not by a long shot.
Like all my relationships that have gone sour, I wouldn't take this one back because I learned a lot: about myself, about him, about the type of people you meet at a Gypsy Kings concert...
Plus I've since been able to add "working with the elderly" to my list of charitable deeds. You're welcome, old man.
