Dating Games: Older, but not wiser

This is my simple question: Why has someone with more than 20 years of dating under his belt not yet found anyone who meets his standards?

Forty Single 311 (photo credit: Courtesy)
Forty Single 311
(photo credit: Courtesy)
I received numerous e-mails following a column printed a few weeks ago called “Dropping the ball.”
The phrase “a great guy who is still single and approaching 40 makes me wonder” provoked a lot of single, over-the-hill men to ask me what I meant.
First, it’s not an insult, and not meant to be offensive.
When a friend who is in her late 20s or early 30s goes on a date with a guy who is 40, it simply leads me to question why someone with more than 20 years of dating under his belt has not yet found anyone who meets his standards.
I’m especially concerned about 40-year-old bachelors – and bachelorettes, for that matter – who have not even been in a relationship serious enough to head in the direction of marriage. Most of the single 40-year-olds I know have either been engaged or lived with someone for many years; but others have no long-term relationship experience, which is highly suspect, and rightly so.
I understand that some people have been busy and invested in their careers. I have sympathy for people who didn’t realize they were being too picky until it was too late. I empathize with people who simply weren’t ready until they were over the hill.
But I do question the person’s willingness to compromise, and his or her compatibility with others.
Most of the men and women I know who are still single and in their 40s are beyond stubborn and not willing to change anything in their lives anymore because they have become too self-sufficient and independent.
Typically these are good traits – but not when taken to such an extreme. These people are so used to being alone that they can’t seem to share their lives in order to make a relationship work.
Unfortunately, circumstances are such that more women than men fall into this category.
My just-turned-40 friend Shelley has been living solo for so long that she has her schedule for every day of the weekend, morning to night, filled a month in advance. As for the rest, from an early-morning bike ride, to a 10-hour workday, to a workout afterwards, to dinner and drinks with friends, to whole weekends away, she is booked solid.
THE ONLY problem is she hasn’t left any room for dating – probably because she doesn’t want to face the music (I’m not sure if this is a conscious or subconscious decision).
And when she does squeeze a guy into her schedule, she immediately judges him and puts up a proverbial wall if he doesn’t pick a restaurant, bar or activity she approves of.
Shelley is a very strong woman because of her predicament. She also has very strong (read: negative) opinions and isn’t afraid to share them, but doesn’t realize she is holding to a double standard when she rejects a man who does the same thing.
On the other hand, I just met newly engaged Larry at a fund-raiser. His love story made me smile because he met his fiancée on a Jewish singles cruise earlier this year.
Larry is a 41-year-old, good-looking, successful and friendly man and although he had actively dated, he had yet to even live with a woman until now. Luckily, he was open enough to go on a singles cruise and didn’t judge the women who had also gotten to the point in their dating careers where they were willing to be held captive on a cruise ship with hundreds of other singles.
I was proud of both Larry and his bride-to-be because most people would be too embarrassed to go on a singles cruise, rather than seeing it as an opportunity to meet someone who is in exactly the same situation.
I’m not saying single, Jewish 40-year-olds should be outcasts or social pariahs or shunned, or anything of the sort. Everyone deserves to find love or to live whichever lifestyle they wish. Rather, I’m looking at this from a perspective of J*Date preferences and singles events and shidduchim.
Every single – no matter his or her age – needs to be open-minded, willing and flexible. That includes those in their 20s, divorcees, widows and, yes, even those who have the bulk of their 30s behind them.
No relationship – friendship, marriage or other – can succeed without compromise.
Both participants have to be prepared to meet in the middle. I know plenty of 30-year-olds who are stuck in their ways; but, luckily for them, they still have time to learn and adjust before their biological clocks tick into overdrive.
I truly hope the 40-year-olds can figure it out before they give up altogether, because it is not a lost cause.