Am I too Old to “Sport F&#k?”

Reader’s Question:

 I’m in my early 50’s, wealthy, and single. I travel often and meet a lot of women. I “sleep” with a lot of them. I don’t know why, it just happens for one reason or another. Am I too old for this “sport f*#&ing?”

So, you like to have casual sex, eh?

Fun Fact:

The term “sport fucking” was first recorded by Playboy in 1968 during a Paul Newman interview.

Fun Fact #2:

Age is just a number!

Not Fun Fact:

Massive amounts of sexual partners increase your chance of unhealthy consequences.

But, you knew all that. Especially the last one.

The point is, you’re self-conscious about your personal life being socially frowned upon. I understand and think it’s healthy to consider outside perspectives.

My opinion stays the same: If you and the other “athlete” are both getting what you want out of this form of relationship, good for you two.

Some people are never drawn to a committed relationship. Some feel happier and perfectly content being single. These people truly don’t want to see someone every single day. They want to come and go as they please, be free of responsibility and the inevitable drama that’s inherent in any relationship. Any relationship that lasts more than a dinner and some “game” time, of course.

This should come as no surprise, but relationships don’t always equal happiness.

All of this goes for lady “sport fuckers,” too. Don’t get me wrong, you’re both sluts, but you’re not bad people.

We all need and want different things. As long as your partner is single, have fun.

Warning! Danger!

Besides the health concerns, you better be sure your fellow “sport fucker” fully understands the rules of the game. This isn’t the start of something new.

Also, this could get tiresome, you are in your 50’s. Most people want a companion to live out our elder years with. You’ll probably want the same at some point.

I work with single, wealthy men every day. These guys are offered their fair share of sex, just like you. Here’s what I’ve seen happen: At some point, women will look at you and think you’re creepy, old, and pathetic.

Just like young, beautiful “trophy wives” have a window of opportunity to find their ideal partner… older, wealthy men can only catch that “prize” for so long.

Just remember, if you ever want more, “jump on” your options while you still have them.

Have fun!

The Remarried Man’s Famous Last Words Were, “I’ll never get married again!” 

Reader’s Question:

I’m 57 years old and have been divorced twice, both times were hell. I’ve met a new woman that I really like and things have been moving along nicely. We have been dating for about a year and I can tell she is ready for things to move forward. However, I do not want to get married, ever again. I am happy to move in together and have this be a long-term, committed relationship. Everything would be the same as marriage, just without vows and legalities. I feel like once you marry a woman she quits trying and I don’t want to go through that again. Any suggestions on how to broach this sensitive issue?

The remarried man’s famous last words were, “I’ll never get married again!”

I totally get it. I’m sympathetic to both sides in this situation. You’re not wrong and neither is she.

This is the second most common issue I encounter as a matchmaker. You’ve been hurt, cheated, and broken. She took a ton of the money she never spent a moment earning or supporting. You thought you knew her. You thought she was different. I have heard it all before. You are not alone.

First, it is unfair to compare or judge your new gal based on previous experiences. We all do this, but it’s best to leave the past in the past, so that it doesn’t control your future. If you’re worried this gal will become the same bad memory as your ex’s, ponder if you’re picking up on similar traits, or simply letting fear rule your perspective.

I have always loved the tradition of marriage, but as I get older, it’s clear to me that good relationships come in all forms. You don’t need a piece of paper to be in love. You don’t need a piece of paper to have a life partner. You can even call each other husband and wife, as there’s no law against this.

Try and share with your partner that you’re in this all the way. Explain that there isn’t another person on this planet that you would rather be with and you hope this lasts forever… you just aren’t interested in signing a contract that says so.


Over the past decade people have begun to utilize legally binding contracts termed, “relationship agreements.” 

While The Big Bang Theory popularized the term in its own particular way, real people use these agreements as a form of commitment that doesn’t reach the level of marriage.

Consider drafting your own relationship agreement and presenting it to her as a sign of your commitment level. While you feel not getting married is a security to you, she is experiencing the exact opposite. A relationship agreement could be the compromise you need.

Now, the “big-ass elephant” I have yet to address.

Your question mentions both wife one and two gave up after marriage. You don’t mention in what ways, and there can be many. The obvious thought of every woman reading this is, “What about men after marriage? Men give up, too!”

Effort levels dipping in various areas of the relationship happens with virtually every couple, on both sides. I preach honesty and effort constantly as a foundation for successful relationships.

Sometimes you push, sometimes you pull. There is a literal give and take a happy couple must comply with.

I know this is hard, but you know this must be worked out to move forward together in life. Have this chat soon. Honestly, I find it a bit odd this took a year to become an issue. Do both of you a favor and let her know where you stand. She can decide if this is a path she is willing to try.

Good luck.

You’re not an “Arrangement Whore,” You’re just Lucky

 Reader’s Question:

 I’ve been dating my guy for a little under a month and things are going well. I’m 34, he is 57, and we live about four hours from each other. We see each other a lot when he is in town and sometimes I visit him. He recently asked me to quit my job so I could be more available to him. He said that he is comfortable supporting me financially each month to give me the freedom to travel more. We haven’t been together very long, so I feel uncomfortable with how this makes me look. What are your thoughts?

You were careful not to use the word, “Arrangement,” but that is exactly what you’re self-conscious about. Every relationship is different and there is no real set of rules. We decide what are acceptable relationship parameters based on past experiences and societal pressures.

When referring to relationships, the term “arrangement” has been soiled over the past decade by adulterers and “gold-diggers.” In truth, every relationship is based on some level of arrangement. Some arrangements (I.e. relationships) are balanced, some more onerous.

As a matchmaker, I see all kinds of different arrangements in relationships. I judge relationships based on one question: Are both people receiving what they want in the relationship?

If the answer is yes, two consenting adults are happy with what they get… with their arrangement… then “to each their own.” Putting people into the relationship they want is the essence of my job.

Attractive ladies that date wealthy men are judged more negatively by the public than a person who claims to be a cat. Makes “purrrfect” sense.

Many adults prefer an arranged relationship. I don’t mean monthly allowance for sex and the occasional arm-candy for galas. I do mean clear boundaries are discussed and what’s expected of each other is made clear.

People judge because they are jealous and bitter.

Websites like SeekingArrangements, WhatsYourPrice, Sugadaddy, and AshleyMadison are all arrangement-based services. The arrangement being sex for money, gifts, trips, et cetera. The ladies that participate in these types of relationships are “working girls.” I still do not judge them because both parties are receiving exactly what they want, but you are not one of them!

Life is hard. Money equals freedom.

In his mind, it makes no sense for you not to quit your job and see him around his schedule. He can afford it and has worked hard to be able to offer such a lifestyle to his gal. Yes, the relationship is new, but he can afford your freedom… BE FREE! He will still be at work! Him arranging for you to quit your job is the natural progression of a relationship with a busy person making lots of money.

The Real Issue

You’re worried about people judging your relationship based on age difference and financial support. You are socially aware those factors are reminiscent of the “gold-diggers” playbook, but do not fret. You aren’t an “arrangement whore,” you’re just lucky.

You’re lucky to be with a guy that can afford freedoms most cannot. You’re lucky to have gotten in to this relationship for the right reasons and have economic abundance as an add-on. You’re lucky to be semi-retired at 34 years old. Most of all, you’re lucky to experience such a care-free relationship.

Shit, I’m jealous. Who wouldn’t be?

Note: I do not actually believe in luck. I use the word here to deliver a point.

Be Careful. Be Prepared.

Your situation is not unique in the world of dating successful men. I have had many of the relationships I match turn out this exact way. So, here is my warning:

Your “luck” can run out quick. Have a plan for a potential break-up.

Being judged by others aside, there is one real drawback to allowing him to support you. If you break-up, you become unemployed, not semi-retired, and quickly broke. So, before you agree to quitting your job, discuss how/if he would help you get back on your feet if things change. This isn’t scummy, this is very necessary. Trust me, I have seen the aftermath of having a plan and not. Be on the side of preparation.

Relationship agreements (i.e. actual contracts) are becoming more and more prevalent due to this exact circumstance.

Otherwise, enjoy!

This is a wonderful opportunity for you both to get to know each other on a deeper level. Plus, he is showing a real commitment on his part. Believe that he wouldn’t give his hard-earned money to any pretty face… he wants you.

I say go for it. Try not to care what everyone else thinks. Only you and your partner know what’s best for your relationship.

 Have fun!

Top Ten Reasons You’re Single

  1. You are unreasonable about what you expect from a partner.
  2. You play too many “hard to get” games.
  3. You are stuck on a previous relationship.
  4. You fall for the gender stereotypes. e.g. He must be tall, dark and alpha. She must be…
  5. You only want to date “the one.”
  6. You are too needy from date one.
  7. You have too much drama in your life and you shout it to the roof tops.
  8. You fear becoming dependent… aka, commitment issues.
  9. You think relationships can be developed online. The internet is a good start, but texting and emailing will never build a proper foundation. Pick up the phone and meet in person.
  10. You are insecure about yourself and send off those vibes without knowing it. It’s unattractive.

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