Compete Network Feature Stories

Bedroom Sports: May-December Relationships: Is It Just About Money?

When I was in college I worked as a server in an upscale restaurant. I was waiting on a table when I asked a mature gentleman if he was there with his son for a special occasion. The gentleman quickly told me that his “son” was actually his longtime boyfriend. It was a mistake I did not make again.

As the world evolves, people are living longer, healthier lives in general and more members of the LGBT community are now openly gay. Because of these changes, the opportunity for an older person to be out in public with a much younger partner is becoming more common.

What do I mean by “much younger?” Well, I am certainly not an expert on what has long been known as May-December romances. But to me, I’d say that it is at least a 20-year age difference. And I’ve known couples that are even 40 or 50 years apart in age.

Typically when I see such a May-December couple my first thought goes to, “I wonder how much the cougar spends on his/her partner?” I guess I always just assume it is about money and perhaps, control. Again, I assume the older partner is the more dominate one in the relationship. But is that assumption really accurate or I am just feeding into stereotypes? After doing some limited research, I must confess I was genuinely feeding into stereotypes.

I started my research online (who doesn’t nowadays?) and joined a dating site for older men looking for younger men.. This was much less a dating website than it was a hookup site. In fact, I kept my profile to a minimum by not answering specific sex questions. I was actually quite shocked by the number of 65-plus-year-old men who were blatantly forward in their quest for a quickie – most of the time they didn’t even say “hi” when messaging me on the site.

Not all men on the site were there for sex. There were a few genuine guys that were true gentleman. They attempted to have a somewhat normal conversation with me, even asking such mundane questions as “how are you?” and “how is the weather?” After about an hour in the online chat room, I’d say I talked to about 9-10 men. And out of that number maybe two were there for more than just sex.

Since I personally prefer men my own age, I began to feel like I was leading on the others in the chat room. So once I had enough notes on online cougar dating, I quickly exited.

The second part of my research began by calling one of my best friends. Although Jacob is 42, he was only 23 when he met Bill, his partner of 18 years. There was a 33-year age difference between them and Bill passed away last year at the age of 73.

Bill was already retired when he met Jacob so they spent 18 years travelling and enjoying life. Now in his early 40s, Jacob was left with a nice trust fund. And if he manages his money well, he’ll never have to work.

I asked Jacob if Bill’s money was one of the reasons he was attracted to Bill. “I have to admit it was,” he said. “Well, not really the money. It was about the security the money provided us. The ability to travel and spend much more time together than a couple in a traditional relationship would be able to spend together.” That does kind of make sense to me. After all, money problems are certainly one of the main reasons relationships don’t work out.

“So it wasn’t really about money,” Jacob went on to say. “It was about security. I trusted Bill’s maturity. I always felt like his life experiences meant something and I could learn from him.” While unconventional to me, I have to admit that Jacob and Bill’s relationship always seemed really positive.

So based on one trip to an online dating service for mature men and a twenty minute conversation with my friend Jacob, I certainly know I am not an expert on the subject of intergenerational dating. While I don’t think it is right for me, I’m no longer quite so skeptical when I see a May-December couple.

When it comes right down to it, relationships, like the people in them, come in all shapes, sizes and needs – it only has to work for the individuals involved. (Oh, and I asked Jacob where he met Bill – he still hasn’t told me.)

By Ryan O’Conner, Guest Columnist

Ryan O’Conner is just a regular guy who is dating in this great big world. His advice comes from personal experience and his advice is for entertainment purposes only. We recommend you consult a physician, counselor or therapist in your area for specific advice about your personal situation. Otherwise, questions can be submitted to [email protected].


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