A few months back, I got a call from a couple of old high school friends of mine who were going to be in town in a few days. We agreed to call a couple of other friends who also lived in Toronto to join us for a reunion dinner. It was a mixed group of four girls and three guys. Some of us hadn’t seen each other in years. It was going to be good to catch up. The anticipated day finally arrived, and there we were in a cozy Queen West restaurant, reminiscing about old times and catching up on what was up with all of us.

One of the girls, let’s call her Linda, was saying how she was happily married and pursuing her passion as an artist. Linda was always the creative one. She would always be in the school plays or reciting poetry at various slams during our university days. She read Noam Chomsky and loved travelling.

Today, she still does all of that and more. A few years back, she met her husband Josh, a corporate lawyer, on one of her trips to New York, and now, she goes back and forth between NYC and T.O., attending art shows and fundraising benefits.

There was also Janet, who became a successful businesswoman. She was always the entrepreneurial one. After our undergrad together, she went on to earn her MBA and opened her first small hotel resort in the Bahamas. She also got married to a wealthy hotel owner. Together, they now own three resorts around the Caribbean.

Among the men, there was Robert. He was also an aspiring artist with some success but was still saving up to buy his first home. Back in the day, Robert was also into acting and spoken word. We all used to go check out his and Linda’s performances at the slams. Today, Robert was in love too with his wife Jasmine. They had met in high school and were still together. I couldn’t help but wonder about some of the reasons why life had taken Linda and Robert, both artists and bohemians at heart, into such different paths.

Granted, there could be tons of reasons why Linda is jet-setting now, and Robert is renewing his monthly TTC pass. While nobody would ever see anything wrong with Linda seeking out a “suitable” life partner to “complement” her bohemian streak, society would certainly be more critical of Robert for scoping out wealthy women to finance his equally noble artistic pursuits. Somehow, it was always assumed by our group of friends that Linda would “marry rich.” Not that she would outright go out and say that she’s looking for money in a man, but she would always make a point of going to the “right” events, bars and social gatherings.

At the risk of sounding sexist, we all know that beautiful women can spend hours at a Yorkville bar drinking all night without ever taking out their purses. At the end of the night, they might end up with a date with a Forest Hill dude with a trust fund. Brothers, have you ever tried doing that? Good luck! In fact, I’ve been told by a female friend of mine that her group of girls has a “rating system” for the city’s restaurants and bars. Of course, the most highly rated spots are where there is a larger concentration of rich guys.

More and more these days, men are starting to observe how good women have had it all these years, and they are now looking to “get theirs,” too. The web is now full of guides for men on “How to Attract and Win a Rich Wife.” I’m not saying that men should go on welfare and wait on a woman to feed them, but men should also take a page from the ladies’ playa book and not overlook the benefits of partnering with rich women who can help them take things to the next level. Look at Janet’s example, for instance. She was an already successful businesswoman who would only consider marrying a more successful partner to advance her prospects further.

Men who do seek wealthy women, however, tend to end up with older women. This is probably why the gold-digging trend isn’t as popular with us men. If all older women looked like Demi Moore or Angela Bassett, I think there would be a lot more Ashton Kutchers running around. But then again, women have been making that ethically challenging choice between true passion and money for years.

Are any wealthy Cougars looking to get their groove back?