Looking for Love in...

It started perfectly logical.

My buddy Dexter stopped by my office the other day. This has been a rough year for him. A serious relationship that was a major pat of his life imploded in the space of thirty days, his job, which he enjoys, just isn’t cutting it, bill wise. Well, he and his ex wife are getting along. I guess every dark cloud has a silver lining.

I leaned back in my new chair and put my Allen Edmonds on the desk.

“What’s up, man?”

“It is what it is, J. Is what it is.”

“You’re looking better, man.” It was true. He’d lost some weight and he was clean. Suit, tie.

“Well, I have a new strategy, man. You know, I’m not into just random encounters. I dig the ladies, though. I’m far from ready to get back out there, but when it’s time, I have a plan.”

He shared it with me. I listened. That evening, I shared it with the first person I knew would listen and not slap me silly. Well, not right away.

“He’s just gonna date twenty year olds,” I explained to my sister Brenda.

“Mmmm Hmmmm…” Bren is a veritable font of wisdom and advice. Her words are few, but oh so powerful.

“They aren’t bitter…they aren’t carrying a buncha baggage…if something goes wrong, they aren’t on some ‘I’m always right it must be you that’s wrong’ page. See, he figures…and by the way? I mean, dude is clearly still a bit confused about his last situation, and reasonably so. I thought that was a definite recipe for happiness. Perhaps that is affecting his judgment.”

Bren sighed. “I remember that girl. If she loved him half as much as he loved her, he wouldn’t be on this silliness now. So exactly WHY is Dex now chasing women half his age?”

“He’s not chasing. When he gets back in the swing of things, he is going to exclusively date twenty year old women attending four year institutions who happen to be close to graduating.”

“Mmmm Hmmm…”

“No, wait…he wants someone who is busy, has some goals, isn’t just looking to get married, etc. “

“And…there are no women his age with which he can accomplish that?”

“Dexter feels not. The last one took the cake. He says he is tired of dealing with women who, when you meet them, their attitude is ‘Woe is me…I’m a good person…why am I alone?” Then, after the honeymoon period, the psychosis emerges, and now you are the devil incarnate, either expected to just do as you are told or take the blame for what every bad jerko they dated in the past did to them. He has that Sean Connery in the Untouchables logic: If you keep getting a bad apple from the barrel, get one off the tree.”

Brenda is 300 miles away. Indianapolis. I could see her look of incredulity via long distance wire.

I continued. “And not HALF his age. We both agreed dating anyone whose age ends in ‘teen’ makes you look like Robert Sylvester. No. Twenty. Young enough to not be disenchanted, young enough to still believe in love and not be jaded into thinking it’s love because they don’t want to be lonely. Old enough to be legal.”

I thought it was humanly impossible to laugh for a straight five minutes.

When Brenda caught her breath, she gasped, “OK, so you realize there are probably gals his age that may know some tricks the young ones don’t…” She started giggling again.

“No, we discussed that. It’s like the guy in the locker room who thinks he is pleasing all the women and doesn’t know the computer nerd is doing his girl. Just because someone believes with age they are super freaky does not mean they are. It’s just what they want to believe. Plus, he figures it’s a win-win. If his twenty year old is out there, then he gets to enjoy some way out encounters with someone who is young and ah…”

Brenda giggled all over again. It took five minutes for her to choke out, “Fresh?”

“Whatever. If she’s NOT out there like that, then guess what? He’s got a pupil. He gets to be the guy who introduces, um, new stuff.”

“OK,” Brenda had it under control, for now. “so what is the appeal?”

“He figures he’s tried everything else. He’s tried women his own age. In too many cases, he finds them manipulative, and immature. He’s tried older women. They are into the whole mother thing. That’s a turn off for him. He has a preference for one type of women, so crossing certain lines is out of the picture.

“Dex wants someone who is going to be nice, and appreciative. Says his luck lately is to hook up with someone who starts off nice and a bit wounded. ‘Why me? I’m a good person.’ Once the relationship progresses, this person starts dragging all of their baggage from past experiences into the relationship. He thinks some people actually LIKE carrying that stuff around.”

Brenda stopped giggling. “Some do. They get off on it. Makes them feel simultaneously they were the victim, AND it was never their fault.”

“Anyway. He says that if he is going to deal with immaturity, manipulation and the whole nine, he might as well take it from someone young, beautiful, unencumbered by extensive drama, or past marriages, or nineteen boyfriends who couldn’t get it right. He figures if eventually he is going to be the bad guy, why not be the bad guy with someone who isn’t yet at an age where they get off commiserating about how evil the opposite sex is, while still chasing the same types of losers that made you miserable in the first place. He figures if he is going to shell out money having fun, which he expects, why not do it with someone who is going to be appreciative, and, hey, may really dig the experience because it’s not their gozillionth time doing something. If he has to be bothered, he says, why not find a group that has not learned to use dishonesty with men as a defense mechanism. Plus a group that still likes to watch cartoons. ”

“Hmmm…”

“He also reminded me of a quote I read once. ‘Men think sex is important. Women know it is useful.’”


“Robert B. Parker?”

“Yeah. Anyway, he admits he thinks it is important, it matters, and he wants to be with someone for whom the act is important, as well. Not just someone acting on urges or thinking they’ll be intimate because they like someone and see they can get something out of it later. He reminded me that when younger women do it, they really like the person. He wants someone who thinks sex is more than just a useful means to an end.”

“Ok. So Dexter has figured out that he wants certain things and assumes no woman his own age is capable of providing them?”

“He likened it to when women decide to only date guys with money. They figure after being dogged and dealing with silliness, they may as well go through it with someone who has something, as opposed to Broke Ass Ray Ray.”

“I hear you. There is some truth to that.”

“What scared me was that he called his cousin at younger Northern and, while scrolling through her Facebook page, asked that she introduce him to ‘all your little top heavy friends.”

“Top heavy?”


“Yeah, he says there’s no way to accurately discern derriere measurements from a Facebook photo…He also said, ‘JD, Moving forward I am only hooking up with 20 year old college gals. I Like these young women. I keep getting older; they all stay the SAME age.”

“That’s from ‘Dazed and Confused’.”

“Great flick. So anyway, he asks her some of these kids’ names, and for each girl, she has, like, nine names! One was T-girl, T-killa, Tyty, Ty-myster, Bffty, or Totally Ty. She was only 18 though. His response? ‘Yeah. See, all that shit is PRECISELY why they have to be 20. I want a woman with ONE DAMN NAME.’”

“He’s hurting, JD. Be nice.”

“Wait…I’m just picturing me and all my creepy 35+ buddies checking our lil sisters' and cousins friends out.”

“Ewwww….”


“So Dex tells his cousin, ‘Yeah. Young women are where it's at. They not all old and bitter. Plus, they happy with Mickey Dees and the little things. Like key chains.”


Brenda and I broke up again. I couldn’t help it.

“Most importantly? Dex wants a GIRLFRIEND. Not a spouse. Not someone to walk off into the sunset. He also figures he has the luxury, when he leaves, of this woman still having some feeling sfor him, since all the women his age still have feelings for the guys from THEIR past. Plus, wives cost too much when they decide to bounce. Dex also sasid too many women have agendas when it comes to marriage. When they're young and want to reach that milestone, they are all for it. When they hit 40, suddenly, marraige is a bad idea, because they don't want someone having access to their assets. Dex says this is sound logic and he, too will apply it, although it will make women mad.

"Dex wants someone to join him at the theater, not parent teacher conferences. He doesn’t want to argue over who raises kids how or feel as if there is any agenda short of them being, well, happy. He just wants to keep it easy, have a good time, with few complications. If things get intimate, he wants it to mean something, not be yet another guy who’s hitting it or worse, be someone who may be getting the sex due to some ulterior motives or a hidden agenda. He wants someone who is going to appreciate the economy is tough and he can’t afford to just ball outta control. He doesn’t want to hear about ex boyfriends, or ex husbands, or have to pay the price because LaMarcus and RonRon messed up. He says he has realized women will complain that is immature, but he finds it equally immature that the women he has known only want to be married to carry out agendas that have little to do with their man or a real partnership.”

“Again…there are no women in his age bracket with which he can do this?”

“Dunno. He was making my head hurt, I was laughing so hard. At one point, he said the fact that he was employed, had a car, liked to go out and was a nice guy would be enough for a twenty year old.”

“Oh, my. So what do you think?”

“Brenda, I think that if you start dating someone that was born when you were seventeen, there are bound to be some issues down the line. Plus, what starts as a girlfriend may end as your wife. You know she’s gonna put his behind in a home one day.”

“Hasn’t happened to Hugh Hefner yet.”