Gay Dating Tips For Senior Men

Gay Dating

4 Gay Dating Tips for Senior Men

Mason Glenn

Written by: Mason Glenn

Mason Glenn

Mason Glenn has had a long career in the matchmaking industry and has spent his time helping high-caliber clientele in Los Angeles select eligible matches. He specializes in working with gay men.

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Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

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Some of my favorite gay dating coaching and matchmaking clients are those who are 50 or older. Over the near decade I’ve worked in the dating and relationship industry, I’ve seen that mature men have time to do the homework I ask them to do. And they want to figure out what truly matters to them in a serious relationship.

I think most of these mature men want to hire me as a professional dating coach and matchmaker because they are done with their hookup phases, and they’ve decided to follow a path to finding the love of their life.

Here are my top four dating tips for mature men to have the best success in dating.

1. Date Someone With a Similar Mental Age

Over the span of eight years working in the dating coaching and matchmaking field, I often hear my clients say, “I’m youthful and want to date someone who’s the same.” I really do believe that age is just a number, but there are certain life skills a 20-year-old guy just doesn’t have that a man in his 50s does.

Something I frequently hear from my older gentlemen clients is that the younger guy they are dating is mature for his age. But then this rift in age started causing them a lot of struggles and indifference down the relationship road. I explored this notion in more detail in my book, but, in general, I’ve found that the larger the age gap between two romantic partners, the more likely compatibility will wane as time goes on. One study shows that the success rate of a long-term relationship with people who have a 20-year age gap is around 5%. That’s extremely low.

Photo of a brain in a hand

It may sound obvious, but if you’re silly and immature at times, then you’ll have more luck in your dating life if you date someone who acts similar.

Age disparity is a real thing that can drastically affect a relationship over the long term. This is one of the main reasons why I always try to match a client with someone who’s within 10 years of their own age. The half-your-age-plus-seven rule to determine the minimum socially acceptable age to date is a tool I’ve seen has some validity. For example, if you are 50, you’ll divide that by two, which will give you 25. Then you’ll add seven, which will give you 32. So you won’t want to date anyone younger than 32.

By all means, please date whomever you wish. It’s your life. I can’t control you, but I can offer my expert advice to help you see blind spots. People pay me to be honest with them. I have to mention these obstacles to my clients (and you as a reader) so they can adjust their expectations as needed.

2. Date Someone of Similar Physical Activity Level

The amount of gloating I hear from my mature clients about their physical fitness prowess is quite extensive, especially since I exclusively match gay men in Los Angeles. This city is all about what you look like. Maybe they feel they have overcome the adversity that comes with the aging process, so they want to convince me that they haven’t let themselves go. Believe me, I have seen men of all shapes and sizes, and I think a lot of those men tend to date people like themselves in that regard.

Some of the fittest men I have met have been over 50. However, just because you have a statuesque physique doesn’t mean you should convince yourself that you only deserve to date someone 20 years younger.

Photo of senior man working out

If you’re very active in your physical, and even social, life, then it’ll be easier to date someone who’s on that playing field as well.

Dating has to be a complete package. The physical side is just one very small piece of the relationship puzzle. I would argue that you need someone to stimulate your mind more than your sexual desires at this point in your life. However, I’m not saying your sexual desires should not be honored. Just because you are older doesn’t mean you aren’t a sexual being anymore.

I also want to talk about social fitness, not just physical fitness. I know for me that, after the COVID-19 pandemic, my social fitness was quite weak, even more so than it was before. I still prefer staying home and cooking dinner rather than going out on any given night. However, I know a lot of mature gay men who are quite the social creatures.

This is an instance when I would say age doesn’t really mean anything. I’ve seen men in their 70s come into my office and talk about how they go out almost every night, attending business networking events, dinners, or game nights with friends. I’m exhausted to even think about doing those things frequently — and I’m 33 years old! But I understand if that’s how they want to live their life, and I understand if they want to find someone who also wants to live life that way.

3. Date Someone Who Can Contribute Somewhat Equally in Terms of Finances

Dating someone younger, less successful, or less financially stable than you can automatically create an atmosphere where you take care of dinner, trips, and things like that more often than you normally would. However, my hope is that if you do these things, the other person offers what he can contribute.

I typically have dated people at least five years older than me. During the start of my dating coaching and matchmaking career, I found myself having to voice to my partner that I cannot afford a fancy dinner or a long vacation. I never expected to have someone pay for me. However, I did expect someone to understand that I can contribute in my own way to the relationship. I never wanted to feel ashamed for not being as successful or financially stable as my partner. It’s important to note that you want to date someone who can actively contribute to the relationship.

Photo of a calculator

Money is one of the biggest reasons couples fight and divorce, so you want to make sure you and your date are on the same page.

A significant number of life decisions are based on finances, so it’s important to have these honest conversations about long-term life decisions. Does this person eventually want to become a homeowner? Does this person expect you to contribute a lot more than what he can contribute to rent, eating out, and traveling?

If you are looking to pay for everything, then you should adjust your expectations on longevity with this person. I will always root for new love, but, to be fair, I also need to pragmatically show you all the paths a relationship can take.

4. Be Honest With Yourself About Your Relationship Goals

Other than dating someone with similar finances, a lot of older men tell me they want to date someone with a passion and who can stimulate interesting conversation. Because these men have lived longer, they have many more interesting stories to share about the fun and learning experiences they’ve had. They also have a lot of knowledge when it comes to dating and relationships.

Photo of the word goals written down

You have to know what you want in your love life to attract the right kind of person.

My hope is that at this point in your life, you know what qualities you seek and want to avoid in an ideal relationship. You’ve had more practice in terms of dating, sex, and love. You want to make sure you find a partner who counteracts your weaknesses and roundss out your strengths. Mature gay men have always seemed more interesting to me than younger gay men. I think intrigue is something they should use to their advantage.

Trust Your Emotional Compass to Guide You to Dating Success

One of my favorite matchmaking stories is the time I paired these two men who were both around 50 years old. They would’ve never thought to date one another because they were only looking for someone who was 10 to 15 years younger. Because their dating styles were so similar, I thought they should totally roll the dice and go on a date. They did, and today they are engaged! The reason I’m telling this story is because I can give you all the advice I want, but, at the end of the day, it just goes to show that you never really know what’s going to happen in life.

Regardless of age, I always tell my dating coaching and matchmaking clients to give themselves the option to be surprised. I’m going to tell you, dear reader, the same thing. Shake up your routine. Don’t believe in stereotypes, rumors, or preexisting notions you may have adopted years ago. Believe in someone’s heart and where they are now mentally and emotionally. Usually having this mental and emotional compass will bring about more awareness to your love life, and you’re more likely to go on more successful dates and have a successful relationship. Have fun!

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