I See How This Works

Note: This is combination of two posts from last year that proved to be very popular. This dialog is a mash-up of all the conversations I’ve had with women this age in the past two years or so. I put it in this format because my normal posts can be too abstract. Many people learn from the dialog approach just as many people require pictures.

A middle-aged fellow is having a libation at an upscale bar and restaurant in a big city. It’s about an hour or so after work and the place is rather full with a white collar, professional crowd in attendance. The protagonist is sitting at the corner of the bar.

A reasonably attractive, early 40s-looking woman sits next to the protagonist but as the bar has a corner, she’s 90 degrees to him. She orders a cosmopolitan and then proceeds to dig her cell phone from her purse to look at it with a hopeful expression on her face. Then a brief and darker look crosses her face.

Our protagonist, an observant fellow, notices that the woman isn’t wearing a wedding or engagement ring. He also notices that her hair is down and her very red lipstick is quite fresh. He glances down and sees high heels that are too tall for work and a skirt that ends just above the knee. Her well-cut jacket covers her blouse so he can’t see what she might be wearing there.

The woman looks up from her cell phone and sips her pink drink and then sighs almost imperceptibly while looking away from the protagonist. She looks back to her drink and the phone.

He finally speaks to her.

“Cheers.”

The woman looks up at him, almost puzzled.

“Oh… cheers” She raises her drink glass and has a sip.

“Pity about your date being cancelled.” He says flatly.

“Do I know you?” The woman has an expression of surprise and wariness.

“Not at all, but I can tell your date cancelled.”

The woman regards him carefully for just a moment, as if assessing a threat.

“How did you know I was even supposed to have a date?”

The protagonist sips his drink – an imported draft beer – as a way of pausing. He then looks at her directly.

“Your heels and skirt are too high for work, your lipstick is also too red for work and it’s fresh. You’re not wearing a wedding or engagement ring, that means you’re single. You were supposed to have a date.”

The woman leans back to look at the protagonist. She raises one eyebrow.

“I could be here to pick up men, did you ever think of that?”

The protagonist smiles wryly.

“We both know there are better places in town for that.”

The woman crosses her arms in front of her and almost glares at the protagonist.

“OK smart guy, how did you know my date was cancelled?”

The protagonist continues.

“You checked your phone as soon as you got here. You had a hopeful look at your face and then you saw something you didn’t like. Probably you got a text just as you entered this place and waited to sit down before you checked it. Also, it’s five minutes past 7:00 so it’s likely you had plans to meet at 7:00. He’s not standing you up because you would be looking like you were anticipating something.”

The woman glares at him.

“What are you, Sherlock Holmes? I don’t think I like this conversation and I think you’re kind of rude.”

She looks around the bar and sees that no empty seats are available. The protagonist calmly takes a sip of his beer.

“I know I’m rude, I’m actually rather good at it.”

“You know you’re rude?” This remark surprises her. “I can’t believe you just said that.”

“Should I continue?”

“You might as well.” The woman lets out an exasperated breath of air.

“OK…you’re not here to meet friends or colleagues because you would have tried to get a table or they would have already been here. I’ll even go out on a limb here… this was supposed to have been your fourth, no, your fifth date with this guy.”

As the protagonist talks, the woman leans in and opens her mouth slightly. Her stare at him is unblinking.

“Fifth date and have you been following me or something? This is really creepy.”

The protagonist sips his drink again.

“Nope, not following you. I have better things to do.”

The woman leans back and opens her eyes widely. The protagonist doesn’t react to her expression. He reaches his hand towards her.

“I’m Douglas.”

The woman reluctantly extends her hand.

“Claire”

“Well, now that we’re not total strangers, should I go on?”

“No, I think you should stop.”

“Fair enough. Pity about your date.”

“Yeah, I know.” Claire turned and sipped at her drink and then turned back to Douglas. “He didn’t even say he’d contact me later, just said he couldn’t make it tonight. He didn’t even apologize. I was about to text him back.”

“It won’t do any good.”

“No? Why is that?” She looks both surprised and crestfallen.

“If he were serious about seeing you again, he would have texted that he would call later or for you to call him, or something like that.”

Clair looks at her drink pensively.

“I had high hopes.”

Douglas smiles thinly.

“We all do, even at our age.”

“Why do men do that?”

“Because we can.”

At this, Claire looks almost angry.

“This conversation is making me uncomfortable. I don’t even know you except for your name.”

Douglas leans back on his bar stool. He crosses his arms.

“Do you want the truth about men and women? I figured out your situation in about minute, I have more to say.”

Claire looks away. Then she looks back at Douglas.

“This is going to be uncomfortable.”

Douglas doesn’t smile.

“Probably”

Claire takes a gulp of her drink, finishing it. She quickly signals the bartender for another.

“You should buy me that drink, you know. It’s what men are supposed to do.”

Douglas smiles wanly.

“It’s what men do who are unsuccessful with women. My beer is almost empty, by the way.”

Claire looks very surprised.

“Wait, you want me to buy you a drink?”

Douglas nods his head slowly with a small smirk outlining his mouth. Claire shakes her head.

“I can’t believe this.” Still, she signals the bartender and points to Doug’s beer.

“Thank you. You’ve never bought a drink for a man before?”

Claire appears thoughtful for a moment.

“Well, I actually bought drinks on the first date with the guy who cancelled tonight’s date.”

Doug continues his questions.

“Has a man ever bought you a drink?”

“Sure, every time I go out with my girlfriends, there’s always some guy buying me and my friends drinks.”

“Have you or your girlfriends ever gone out with a guy who’s bought you a drink?”

“No, not that I know of…” Claire catches herself. “I don’t get your point.”

Douglas leans back.

“You just made my point for me. Guys who buy drinks for women don’t usually go out with those women.”

Claire makes a skeptical face while sipping her drink that the bartender has just brought over. Douglas’s beer is now fresh.

“So Mister smarty-pants, you were going to tell me about men and women.”

Douglas replies quickly.

“Not the younger generation, only people in our generation.”

“That makes sense. So what about people in our generation?”

Douglas takes a long drink of his beer before he responds.

“Dating is different than when we were young.”

Claire is not impressed and her face shows it.

“Tell me something I don’t already know.”

Douglas looks at her as he puts down his beer.’

“You’ve been divorced for about four years now, right?”

Claire doesn’t appear surprised.

“Almost five.”

“You’ve had at least one boyfriend and several short-term relationships since you started dating again.”

Claire puts an annoyed look her face.

“I really think you’re a private investigator or something.

“I know probabilities and demographics. People are shockingly predictable if you know their age, where they live, and their education.”

Claire leans back and crosses her arms in front of her.

“So where do I live and how many kids do I have?”

Douglas names a suburban community. “And you have three kids, all teenagers. The oldest is applying for college.”

“Fuck, it’s uncanny what you know about me.”

Douglas smirks broadly.

“Nice girls don’t curse.”

“Now you’re being rude again.” Claire is smiling, but not showing any teeth.

“Like I said, I’m good at that.” Douglas continues his smirk and drinks his beer.

“OK, back to this dating thing, you’ve got me intrigued.” Claire tells him.

“Let me ask you a question, where do you get your dating advice?”

Claire looks thoughtful for a moment.

“Well, in the beginning, I didn’t really ask anyone and I didn’t get any dates. Then I started talking to my single girlfriends and then started to get set up on dates through them.”

“How did that go?”

“I don’t know… it was good it was bad… the men seemed so lost and I was so uncomfortable…” Her voices trails off.

“What were you looking for?”

“What my friends told me, for chemistry, whatever that is.”

Douglas laughs softly.

“We both know what chemistry is.”

Claire looks puzzled.

“I really don’t know. I think it’s supposed to be love at first sight or something.”

“Don’t believe the fairy tale, we both too old for that. Chemistry is sexual arousal, nothing more.”

“Hmm, I don’t know about that…”

Douglas puts on a determined look.

“Look at it this way, if you didn’t feel some sort of physical attraction for a guy and very quickly, would you sleep with him?”

Clair almost scoffs

“Of course, I wouldn’t, that’s kind of a stupid question.”

Douglas smiles.

“Welcome to chemistry.”

Claire still looks puzzled. Douglas moves on.

“We’ll get back to that later. I’m curious about how you met the men you have dated.”

“Well, a few were setups from friends, divorced guys my age. Most of them wouldn’t shut up about their exes and the shitty deal they got in their divorces. I didn’t feel like a date, I felt like a psychologist.”

Douglas rolls his eyes.

“Guys shouldn’t do that, but they’re told to do that.”

Claire again looks puzzled.

“They’re told to bitch and moan about their ex-wives? They don’t know how off-putting that is?”

Douglas leans in.

“Do you remember the late 70s and early 80s?”

“I was pretty young, but yes.”

“Well, that was a time when men were expected to be more in touch with their feelings, to be more sensitive, to be more emotional and less macho.”

Clair laughs a bit and sips her drink.

“Yeah, don’t be macho, I remember that. But men should be more in touch with their feelings and be willing to open up.”

Douglas wears a satisfied look on his face.

“You’ve proved my point again. Those pissed off divorced men you dated? Yah, they were simply being in touch with their feelings and being more emotional. They were doing what was expected of them as they were growing up.”

Claire looks a bit dubious.

“I guess I see your point.”

“I know you see my point.

“You’re kind of arrogant, do you know that?” Claire doesn’t sound insulting, her voice sounds almost bemused.

Douglas smiles.

“I’m rude and arrogant… one more insult and I’ll get a hat trick.”

Clair smiles and turns to signal to the bartender for another round of drinks for both of them.

“I thought this was going to be uncomfortable, but it’s not.”

Douglas looks serious.

“We’ll get to that part.”

Clair looks equally serious.

“If you’re trying to pick me up, it’s not working.”

Douglas leans in as closely to her as the corner of the bar will allow.

“I’m not trying to pick you up. I’m not even going to ask for your phone number.”

Clair looks surprised.

“What if I gave you my phone number?”

Douglas is still leaning in closely and almost whispers.

“I wouldn’t call you.”

Claire is taken aback.

“You’re a jerk!”

Douglas leans back quickly and throws up his hands.

“Insult hat track! The crowd goes wild!” Several bar patrons turn to look at him.

Clair looks exasperated.

“OK, can we move on here? You were going to tell me about men and women and dating… because you’re so smart and all.”

Douglas swiftly changes his mood to be more serious.

“Before I do, I want to ask you some more questions.”

“OK, go ahead.”

“After you dealt with those burnt out divorced guys, how did you meet your dates?”

Claire lowers her voice.

“I tried online dating. A couple of friends recommended it… but I was really hesitant.”

Douglas sounds reassuring.

“Online dating can work and there’s no need to be embarrassed with doing that.”

“Well, I was kind of embarrassed, but I did meet men.”

“See? It can work.”

“I guess you’re right, I met my ex-boyfriend that way, that was just over a year ago.”

“But it didn’t work out, right?”

“Yeah, we were together about three months. I guess it was good but he was a single father and always busy with his kids and I was really busy at work so it just sort of fizzled…”

“Sorry to hear it, but this is the age for dealing with kids and careers, it’s tough for mothers and fathers.”

Douglas shifts the conversation a bit.

“So tell me more about your online dating experience.”

“It was real hit or miss. The emails I sent out, I never got a response. The emails I received were from totally unsuitable guys, my ex-boyfriend and a few others were the exceptions. I haven’t gone back to online dating since we broke up.”

Douglas has a disappointed look.

“That’s a fairly common experience for women, especially after about 40 or so.”

Claire has an almost pleading expression.

“Why is that?”

“This is where it gets uncomfortable. I fully expect you to throw your drink in my face.”

Claire looks serious.

“I promise I won’t do that.”

“I’ll take you at your word. The reason those guys never responded to your online dating messages is that they are attractive to most women. They have options. So, they date younger women. Women in their 40s have the hardest time dating because they expect to get the same kind of guys they could get when they were younger.”

Claire takes on an odd expression that’s part defensive, part sad.

“Women in their 40s are fabulous. They’ve accomplished so much, they’re beautiful, they have so much to offer. I don’t understand why men don’t find them attractive.”

Douglas looks away briefly and then addresses Claire.

“You mean why don’t the tall, attractive, confident, and successful men find you attractive.”

Claire crosses her arms defensively and stares at Douglas.

“Now this is uncomfortable. Are you telling me I’m not attractive?”

Douglas lets out a sigh.

“The guys you want? Those are guys that most 40-something woman wants. Compared to the 20-somethings and 30-somethings they could easily date, you’re not attractive enough.”

Claire is visibly upset and takes a big swallow of her drink.

“That’s bullshit and you know it. Women get better with age. Men should know that.”

Douglas doesn’t retreat.

“Who says?”

Claire throws up her arms.

“Everyone! I’ve even heard a lot of men say it.”

“OK, I know everyone says that. But those are just words.”

Claire quickly takes on a more questioning mien.

“Just words? I don’t understand.”

“It’s the whole words versus actions thing. A confident, good-looking guy might say he finds 40-something women attractive but his actions are different in that he only dates younger women.”

“Then he’s being stupid.”

“And he’s also keeping the peace and getting what he wants.”

“Men are so stupid.”

“From your point of view and because you’re not getting what you want from certain men, yes, they’re stupid. But let’s move on. I want to know about the other guys you met online.”

Claire is still in defense mode.

“Look, I’m answering all these questions about me and I know nothing about you, just your name. I don’t think that’s fair.”

Douglas is conciliatory.

“I’ll tell you anything you want to know but first tell me more about your online dating experiences.”

Claire is not completely satisfied yet she acquiesces.

“OK, I did respond to some messages and went out with a few guys. They were all pretty nice but not serious long term potential.”

“Why not?”

“I don’t know, they just didn’t feel right to me.”

“It’s that chemistry thing.”

Clair looks surprised and relieved.

“Yes! That’s it! There was no chemistry!”

“Not uncommon. How many messages did you get from guys?”

Claire changes her expression to mild sadness.

“I got a couple a day. Mostly from older guys or really younger guys. The messages were either really long like they were desperate or they were really short like they didn’t care that much. I got some messages from married guys who said they weren’t happy. It was so frustrating.”

“That’s a common experience.”

“You seem to know an awful lot about this.”

“I do a lot of online dating.”

Claire looks almost triumphant

“Finally, I get to learn something about you… you’re single!” She pauses and regards him more closely. “Oh… shit… I remember. Is that why you wouldn’t call me if I gave you my number?”

Douglas laughs loudly and honestly.

“You didn’t respond to my message back then, did you. Don’t worry it took a while for me to remember your profile and match you with the photo. I look at a lot of female profiles.”

Claire is obviously embarrassed and swallows a large gulp of her drink, emptying it.

“I need another drink. You do too. It’s on me again.”

She signals the bartender. Drinks are delivered.

Douglas mollifies her embarrassment.

“Don’t worry, most women didn’t respond. I’m not going to ask you why you didn’t respond, that was last year.

Clair still remains embarrassed.

“I just… well… ”

Douglas leans in.

“Stop it, I’m an adult. I don’t take it personally. I send out so many messages and get so few responses. I’m used to it.

Claire’s voice is soft.

“I’m sorry”

Douglas laughs again.

“Good Lord, woman, don’t worry about it! But if you’re ashamed and sorry, so be it. You can do me a favor. Consider it an educational exercise.”

Claire’s face brightens and she nods her head.

“OK, what do I have to do?”

Douglas looks around the bar until he sees what he needs.

“Look over you left shoulder. Do you see those three guys standing around the high-top table?

Claire does what she’s asked.

“I see them.”

“Good. Assume they are single tell me about their dating potential for you.”

Claire looks at them a bit surreptitiously.

“Hmmmm, the guy with the long hair has a pony tail so forget him. The middle guy, he’s got a weak chin and I think his eyes are too close together so he’s out. The last guy… way too short.”

Douglas puts on a subtle smirk.

“OK, did you know what you just did?”

“I’m sure you’re going to tell me.”

“You rejected three guys without even hearing their voices, just on their appearance.”

Claire looks confused.

“I don’t understand.”

“It’s a matter of mindset. A woman usually finds a reason to reject a guy before she’s intimate with him. This is especially true with online dating. There’s always a reason to reject a guy and there’s always another profile to look at or message to read. So, after awhile, there are practically no guys left.”

Claire is unconvinced.

“I still don’t understand.”

Douglas is not fazed but this.

“I want you to look at those three guys again but this time I want you find something positive about them.”

Claire doesn’t look convinced.

“I don’t know about this…” She turns again to regard the three men. “Ok… the long-haired guy, he has nice blue eyes…”

Douglas is pleased.

“Good, now the other two?”

Claire looks again, taking her time.

“The middle guy… hmmmm… actually, he has really nice hair… and the short guy, that’s easy, he’s really well dressed.” She turns back to face Douglas who was smiling.

“See that wasn’t so hard, was it?”

“I don’t see your point.”

“When you look for something good, you usually find it.”

Claire is still unconvinced.

“Platitudes… just platitudes… I’m not going to date any of those guys, after all.”

“I know, but when you start doing online dating again, you need to be able to see guys in a different light.”

“Who says I’m going to start online dating again?”

Douglas looks pleased with himself.

“I do because it’s inevitable. After your cancelled date, your conversation with me, and that little learning exercise, you’ll be re-writing your profile and looking at guy’s profiles, but differently.”

Claire takes on a coy look.

“If I put up my profile again, are you going to send me a message?”

Douglas smirks broadly.

“Would you respond to a message from a rude, arrogant, jerk?”

Claire laughs lightly.

“Maybe.”

Douglas shifts in his seat.

“It’s time for me to leave.”

Claire is a little disappointed.

“This is the best conversation I’ve had in a long time.”

“It’s been interesting to say the least.”

“And you’re not going to give me your phone number and you won’t call me if I gave you mine.”

Douglas is firm.

“I’m a man, I am bound by my word. Thanks for the drinks.”

Claire watches him leave.

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