Cheryl: female, 48 years old, single

I’ve known Cheryl for about ten years.  She is a very-high-achieving attorney, perfectly fit, highly attractive, and looks several years younger than her age.  She’s a good friend to the people she likes, but readily admits to “flipping off” a few drivers on her daily drive home from work.  In fact, I remember one evening (before she knew it was me) she recklessly raced her car around mine as our building’s garage door opened, just to gain a fraction of a second.  

As friends, we laugh and have lots of fun going out together. I doubt she’d argue about being labeled as “assertive”; in fact, I doubt she’d feel the slightest bit of remorse or embarrassment about that label.  She’d probably consider it a failing in those who didn’t do the same, and she doesn’t really care if her assertiveness offends someone.

Although Cheryl is highly self-sufficient, she’d love to have a life partner, but feels she’s “stuck”.  “I don’t meet people. I don’t know people who meet people. I’ve spent lots of times on dating web sites and apps, but I just don’t have the energy to go through the process.”

Here’s Cheryl’s essentials list:

1. Passion/Attraction/Chemistry: “ He needs to be physically fit and must be over 6 feet tall.  I don’t get attracted to anyone shorter than that…He must be athletic, tall. and have a healthy lifestyle, not someone who likes spending their nights drinking wine and going to the latest restaurants….I’m into eating healthy and working out…caring about your appearance is a sign of discipline.  I have it and they need it, too.  I don’t care if they’re black or white, but I’m not attracted to Middle Eastern or Asian men.”
2. Honesty:  “I’ve had my share of dishonest people.  I give them the benefit of the doubt untill I’m proven wrong.  I can tell a lot by how much they share about themselves and the type of relationships they have with their friends and family. It’s a red flag if they’re talking shit about their ex-wife, sister, or mother.”
3. Confident:  “Confidence  goes hand and hand with success.  It’s damaging to a relationship when men are not comfortable with the amount of money they make or where they are in their careers.  I don’t date hot young guys who are trying to become somebody;  I want someone who’s already established.  Men get intimidated by a woman who’s a professional if they’re not on the same level or higher.  An insecure man leads to bad communication, ghosting, shooting from the hip.  I want someone who can take care of shit.  I don’t want to feel insecure that if something happened to me, he couldn’t take care of me.  I’m not in a position to carry someone else.  They have to add value to me.”
4. Someone I Can Admire: “At the end of the day, I want us to share what happened at work. I want them to be inspiring, someone I can look up to.” 
5. Communicate Openly: “I don’t want to try and figure out what they they’re trying to say.  I’m very open.  If I feel a certain way, I’ll tell them.  I don’t want to read their minds.”

The first thing that struck me about Cheryl’s list was that passion/attraction/chemistry is the first, and most important thing, on her list. Most people in their 40s and 50s begin to lower the importance of physical attraction and correspondingly raise the personality traits that have caused such grief in their prior relationships (e.g., honesty, wanting the same type of a relationship, intelligence, niceness…).  

When I brought this up to her, she held fast and reaffirmed that a relationship would not happen if the guy did not have an athletic, fit body.  In fact, about an hour after the interview she texted me “BTW my libido is just fine (probably referring to physical attraction being less important as we approach 50). Dunno who you were talking about,” followed by a smiley face emoji with tears.  

Although Cheryl’s list included important basic requirements like honesty and communication, she emphasized confidence.  This is how she explained it: “Men get intimidated by professional women if they’re not at the same level or higher.” 

Cheryl’s fourth essential was “Someone I can admire.”  Like her last essential, confidence, she wanted someone who is equally if not more financially successful than herself. 

This is how she responded when I asked her about the typical essential traits that she didn’t mention:

Wanting the same type of relationship: “I’m not on a time line.  I’m interested in a long-term relationship.”

Intelligence: “They don’t need a medical or legal degree, but intelligence is very important to me. He should be well read, travelled, and street-smart.”

Nice: I asked her about this trait three times and she didn’t seem to understand what I was asking.  She repeatedly said in slightly altered ways, “I want a long-term relationship”.  I gave her examples, like someone who’s nice to his waiter, or helps someone in need of assistance. When she understood what I was asking she responded, “If they’re at a gathering, I will see the interactions they have and how they treat their employees and whether they have long-term friends.” It didn’t seem to be a character trait she was overly concerned about.  Possibly she trusted her ability to spot it with little effort.

Many of the people I’ve interviewed had essentials lists which were vague or didn’t clearly express their real desires, but not Cheryl’s.  She knew exactly what she wanted and didn’t pull any punches. 

So the next question we should ask ourselves is whether we are offering the same essential traits that we are seeking.  She does.  She’s in perfect shape, very successful, smart, honest, and confident.  

So why is she having a hard time finding her match? It’s not from a lack of effort.  She’s visited more than a few web sites and had many dates, but was frustrated as it hadn’t “led to anything.”

Cheryl is looking for a highly successful man, who’s tall, handsome and in very good shape.  He expresses himself well, has confidence, and “takes care of shit.”  Cheryl is an equal partner, but not a common life partner. 

We should visualize the person we want in our lives and question the typical needs or desires a person like this has.  How does it align with us, who we are and how we portray ourselves?  In this case, the man Cheryl describes often seeks a significantly younger woman than himself who is less assertive  and aggressive and takes a traditionally more passive and softer role.  

Can Cheryl be someone she’s not? Of course not, nor should she.  But we can recognize the needs of the man or woman we desire and fulfill them when we can.  Relationships are give-and-take.  Too much, and it’s not acceptable to who we are.  Too rigid and we miss the opportunity to grow and improve ourselves. It’s a balance that should make us pause and look inward.

When I showed this interview to a friend, she said, “If she was a guy, she’d have no problem meeting this woman, although she may not make as much money as him.  Since she’s a female, she’d have no problem meeting a personal-trainer type who’s built well and is very attractive, but won’t make as much money as her.  He might even welcome her assertiveness.”

This struck me as true.  It may not always be correct nor is it politically correct, but it’s something worth contemplating nonetheless.  It takes courage to talk to ourselves honestly and look at life head on, as it is, then assess and reassess the path we choose to take.