He wanted this

The Complete and Total Loser wanted to be part of a couple his entire life. 
He wanted to fuck seven times a week in his twenties, four times a week in his thirties, three times a week in his forties and have that change to occasional, gentle, medication-assisted copulation from his late 50s on. 
But no. That basic knowledge of what to say to girls wasn't pre-installed in the Loser's grey matter, and he was too self centered to learn it on his own. 
He was so stupid he couldn't see that what he was doing would never work. Now, the Loser downloads books illegally from bit torrent sites about how to meet and talk to women. The advice often sounds silly to the Loser but the overwhelming motif is not: Practice. Get out there and meet people. Crash and burn, rise up; crash and burn again, rise up again. Repeat. 
In his mid-50s now, the Loser lacks the energy to do this and he is so far behind. He doesn't even know how to dress! He doesn't think about it as much as he did. The loneliness isn't a continuing ache now but a sharp pang, which hits him once a month or so. The Loser knows he'll never have what this elderly couple on a bench at a Trader Joe's has. It's too late for that.

A perfect couple

Great hair, great skin, but her feet didn't reach the floor.

She couldn't have been taller than 4' 11". He was maybe 5' 4". But they fit together so well you wouldn't dream of using the word "short" to describe them. He was masculine, she feminine, and they enjoyed each others' company. On the train platform she, in a moment of mock exasperation, leaned her head into his chest. The Complete and Total Loser, seeing this, would have given anything to be that man at that moment.

Two Dating Messages

He'd be an awful spy, the Complete and Total Loser, as bad at it as he's been at everything else. Take this dumb experiment he's been conducting on a dating site, where he's presented a persona that is the opposite of him.
Every time he gets a message he nearly jumps on his keyboard to ask them out, forgetting for a moment that he's lied about everything on his profile and even the picture used isn't of him.
And get this response to two recent messages on the same day:
Woman #1 writes this:
"You are an asshole."
Woman #2 writes this:
"Love your profile. Straight and to the point. Refreshing."
Now, given that the profile is a fictitious one of a man who is the opposite of the Loser, you'd think he'd say something nice to Woman #1 and ignore Woman #2.
But no.
He writes back to Woman #1, this: "Well, you're fat, semi-literate and single, so I can understand your bitterness. I hope you can work through it and be happier than you are now. Keep trying! Never lose hope!"
Coward that the Loser is, he then blocked her from responding.
And he writes this to Woman #2: "Thanks, Krissy. Earlier today I got a message from another woman which said only this: 'You are an asshole.' If you were older and lived closer, who knows?" 
Does this make any sense? Nope. 

Women for Men on Craigslist Post Titles

Taking a chance
Boyfriend Wanted
My breasts need a play date
Drain those heavy balls in my mouth!
Genuine gentleman
Today
Looking for an honest hard-working man
With love, friendship, family and fun
BBW. Ok … who’s left?
Looking for the real thing
Looking for my soulmate
Sexy BBW
SBF seeking SWM
I’m a nice woman looking for love
Looking for a great friend and possibly a great man
Tired of being lonely
Seeking a burly tattooed man
Where have all the cowboys gone?
Searching mature SWF
Searching for my best friend
Beautiful SBW seeks SWM
Serious dating/relationship
BBW looking for someone who enjoys life
Tall SBG looking for tall SBM for friendship
Friends first
BBW looking for teddy bear
Skype?
Professional African woman
Looking for that special someone. Could it be you?
Any Latinos?
Looking for a good relationship
Looking for a down-to-earth guy
Seeking my submissive boyfriend
Waiting for this ...

First Updike

The Complete and Total Loser read his first John Updike novel earlier this fall.
He had preferred John Cheever to Updike but the novel he read floored him by being so good.
The novel was "Couples," which Updike published in 1968 and is about a group of couples in a New England town near Boston in 1963.
The Loser has trouble following plots and keeping track of who's who and, while "Couples" is not a hard read despite its eloquent sentences, he had to make a list of who was married to whom a third of the way into the book. He also began rereading the book less than half way through it. This underlines his well-known stupidity: he was rereading a book he hadn't even read yet.
Updike was a poet as well as a novelist, essayist and critic, and it shows on every page. The Loser's slack jaw would drop open regularly when reading things like this:

This frightened him, and altered the tone of his body. She felt this and opened her eyes; their Coke-bottle green was flecked with wilt. Her pupils in the sun were as small as the core of a pencil.

"The tone of his body," "flecked with wilt," "as small as the core of a pencil." That's in three sentences in a 458-page novel, and he maintains it throughout.
The book is largely about adultery and has many racy yet un-pornographic parts. The Loser, who has not been with a woman in this century, appreciated the Updike makes you feel as if you've spent time with the characters in "Couples."