Dating An Older Man

Gay Dating

Dating an Older Man

Jonathan Welford
Jonathan Welford Updated:
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The gay world can be very open minded about many things. In previous decades, being gay seemed to eradicate (for a while anyway) social distinctions — class, money and employment status.

Many relationships worked very well (a CEO dating a waiter, for example) and status wasn’t really an issue.

In the straight world, when an older man dates a younger woman, these relationships can work successfully for both concerned.

The older man might feel he has an improved “stud-like” status and the woman may feel she has established herself at a higher level.

OK, she might be classed as a gold digger, but it’s an accepted and well-trodden path.

Does the same apply in the gay world?

The answer is yes.

In my dating life, prior to marrying my husband, I was always attracted to and dated older men.

There was something about an older masculine man established in life, knowing his own mind and with a life plan worked out. I liked the idea of this structure.

There are many other reasons younger guys are attracted to older men. Through the ‘80s and ‘90s, if you were older, you were thought to have escaped the AIDS epidemic — this was a trophy in itself.

Today, there is a whole genre of “Daddy Chasers” that shows there is an aesthetic appeal toward older guys (and the fantasies that revolve around them).


“You have to appreciate you may experience

some resistance from friends and family.”

Why didn’t I marry someone older than me?

Well I had the opportunity to do so, but it just didn’t sit right for me and my personal choices at the time.

When you are in your 20s, a guy in his 40s doesn’t seem that old. However, when you’re in your 30s dating someone in their 50s, situations do arise (and certain things don’t rise to the occasion).

Perhaps I’d grown up to be the man I wanted to be through the experiences of dating older men and found a man and partner with whom we could grow old together.

The things to consider looking at when dating an older man are:

1. Older men have experience and you can learn from them.

However, sometimes the adage, “You can’t teach an old dog new tricks” can also apply. As we get older, we get into a comfortable routine and it’s not as easy to change.

2. Age doesn’t matter when you’re fit and healthy.

But when one of you is near to retirement, the body does slow down and this can mean the life in the fast lane quickly turns into slow Sunday drives along a country road.

3. Finances.

In the last couple of decades, people have had more flexibility around their career options and increased choice has become the norm.

Some people have jumped from one job/career to another, and although they have the experience that age brings, they don’t necessarily have the financial stability and rewards.

4. Resistance from family and friends.

You have to appreciate that you may experience some resistance from friends and family. Think about introducing your parents to a partner that is the same age as (or older than) your father.

Likewise, integrating into an older crowd can be hugely valuable, but if you’d prefer to go out drinking and dancing, you may find that a bridge night doesn’t do it for you.

5. A partner passes away.

If you’re looking at a long-term relationship, prepare yourself for your partner passing away before you.

When you are older, will you want to be single or getting back into the dating pool again?

The above points may seem negative and you may feel I’m advising against dating an older gentleman, but many relationships do work.

You have to enter them with your eyes wide open. I value the time I’ve spent with older guys, and I hope they do, too.

Be honest and open, and if it’s a temporary relationship for you and a permanent relationship to the other guy, you need to be fair to him and end the relationship.

The older you get, the more challenging it becomes to create a good relationship.

What are your experiences with dating older men?