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!

Prenups are sooo unfair…


Reader’s Question:

My fiancée and I have been dating for a few years and we are now engaged. When we first started dating, he gave me a heads-up. If we ever decided to get married, I would be required to sign a prenup agreement. I laughed it off at the time, but now it’s not so funny. He says that he can live his life more openly and securely if he knows he has this plan. I feel like it’s his plan for when he is done with me. I’m not marrying him for money, but I want us to take care of each other in various ways, including sharing resources. Do people use a prenup anymore? How do they go into a marriage knowing they are planning for a divorce? How do they get over the initial hurt and insult of a marriage contract?

Congratulations on getting engaged! Yes, of course, people still protect their life earnings before marrying someone that wasn’t there for the struggle.

45.2% of American adults are single, so finding someone you can spend the rest of your life with is an accomplishment!

I’ll admit, I’m pro- prenup. You should be too. There will certainly be protections for your financial well-being as well.

The fact is over 45.9% of marriages today end in divorce. Both parties should decide on protection while they still like one another, and that is the purpose of the prenup. Divorce often causes the most monstrous traits of a person to take over. While they may come to regret their behavior, a prenup will ensure no permanent damage is done.

A prenup doesn’t mean that you don’t share resources, so try and move on from that thought. It makes you sound quite “gold-diggy.”

You aren’t going to want to hear the truth, but the money he made before you, isn’t your money. Nor should you be entitled to it just because you get married. That’s his money. He earned it. You should respect what he has accomplished and not expect him to be okay with you clearly wanting the chance to take it.

If you were marrying a man that had no real wealth, this wouldn’t be an issue.

When you are married, his money is your money and as you stated, resources will be shared.

Not that you would admit this, but if you had the big bank account and not him, would you still hate prenups? Would you even be interested in him if you had more money?

I’m not saying sign whatever he puts in front of you!

Get a lawyer and do your best to secure what you think is fair via the prenup. Then, go plan an amazing wedding and enjoy those hard to find resources. Focus on having a happy and healthy marriage, then none of this matters.

I hope you try and be reasonable about this. If you are having a hard time finding a reason, re-read this blog.

Good luck!



Self-Love: Take Better Care of Us!

I am dangerously close to being 40 years old, so I started washing my face!

The past couple of years have been trying ones. As I turn 38, I’m starting to realize I need to make some “late in the game” changes.

It’s funny… I’m a confident gal both inside and out. I have a great family and I obviously love my job. “First world” complaints are really all I have. However, as 38 years old gets closer, I am freaking out.

Life might be good, but damn it’s hard to get old.

Somewhere over the years, I forgot to love and care for myself. I didn’t really forget, more like didn’t make it a priority. I gave minimal effort to what I looked like and how well I took care of myself: emotionally, physically, and mentally.

I wouldn’t call this “letting myself go,” but it was close.

Now more than ever, I regret letting those bad habits continue for so long. I could blame school, work, kids, my husband, and so on. But, placing blame and making excuse helps no one.

I did this to myself and only I can fix it. Ugh…

So… Where do I start? How do I regain control?

As a relationship expert, I work with people on every aspect of their life. From love and sex to business and parenthood. I confidently lead others to find their best possible self, but how do I take my own advice?

First things first, I washed my face. This may seem weird to you, but I’ve really never bothered with it before.

So now I wash my face, daily. It’s a small thing. I’m sure you’re laughing at me, but this has taken some serious effort on my part. I actually had to set an alarm for the first two weeks as a reminder.

So, one baby step towards self-improvement. Check!

Next, I started back to the gym. I freaking hate the gym. I have exercised a bit here and there because my husband kept on talking about being healthy and some other stuff. I don’t really know. I didn’t pay much attention.

This is no longer a baby step. I have been working out five days a week for over a month now. I have also given up sugar, my only true love… sorry kids.

I’m now making actual lifestyle changes because I need to love me more. I need to be stronger and healthier and happier for me. There is no excuse not to be my best possible self. It’s all about effort. There is enough time if you make it happen.

This is my new way of life. It keeps me balanced and centered. Going to the gym in the morning helps me to start my day feeling like I’ve accomplished something for me.

For those that are unaware, I am not a moderate person. It’s all or nothing for me, no matter what. So, beyond the changes already mentioned, I focused in on smaller bad habits as well, like biting my nails.

Over the next few months, I plan to continue my journey to a happier and healthier me. I’ll learn to love me again.

If you don’t love yourself, how can you love someone else?

Self-love is very important. When you have a strong sense of who you are and your own value, you’re able to have healthier and happier relationships in your life.

Loving yourself and having self-worth is an endless process which takes effort just like any relationship. Loving yourself is a choice you make every single day. Loving yourself must be a way of life. I am working towards taking care of myself as a new habit. Loving me for me, all day, every day, because I should and I can.

What’s the point?

If you have “let yourself go,” or simply stopped making sure your needs are taken care of… for whatever reasons, make changes now!

Good luck and stay mentally tough.

PSA: First Date Conversation

As a relationship expert, I do a lot of coaching. I constantly hear he/she did not bother to ask anything (on a date) about me, except my age, marital history, and income.

A first date can be uncomfortable, especially if you arrive with a bad attitude or don’t even attempt to give the other person a chance. However, if you can walk into a first date with a great attitude and no expectations, things will go much smoother… this is actually true with everything in life!

During a first date, both people are supposed to use this time to get to know one another a little better. The keyword here is …BOTH… but at least seventy percent of the time this doesn’t happen.

We’ve all been on that date when one person is so self-absorbed that they spend the entire time talking about themselves, what they have, where they have been, or who they know. (This is a RED flag)

FYI: If a first date conversation includes: Can you show me photos of your ex’s? How much money do you make? How big is your house? How many cars do you have?… RUN! Don’t waste your time lecturing an adult with poor priorities, just leave.

So, today I want to set the record straight with a few extremely basic guidelines:

  1. Remember, a first date is also the first impression, and first dates are inherently awkward. Which means the first impression may not be so great, either. As long as the person seems nice enough, you share some basic interests, and there is some chemistry, try for date number two. On your second date, things are generally way more comfortable and you can really get a better idea of who someone is.
  2. Always go with your gut. If you go out on a first date and leave with the feeling that something is just not right (i.e your instincts are warning you, not a superficial judgment), then maybe just move on to someone that doesn’t make you uncomfortable to be around. Don’t waste time here…
  3. Ask questions, appropriate questions, and lots of them! Ask about interests, life goals, family, pets, favorite foods, or television shows. Ask about holidays, culture, and even if they enjoy their career. Don’t talk about break-ups, divorces, finances, how you want a baby by date three, or anything else that you would not disclose to a total stranger. Use this time to get to know someone and allow them to get to know you. This is NOT an interview and should be fun and relaxing.
  4. Lastly, please stop with the games. There is no winner when this happens. Grow up. If you don’t want a second date, say it. If you like someone, tell them. If you want a second date, ask right away. Don’t wait around because you don’t want to seem too excited or desperate. Pick up the damn phone and call.

“The early bird gets the amazing relationship!”

I Will be Alone for the Rest of My Life

Reader’s Question:

 I am not an attractive man and it doesn’t help that I am short (5’3”) with a below average penis. I was in my late twenties before I finally had my first date and at thirty-five, I am still a virgin, as a refuse to sleep with escorts. I am not suicidal or depressed, but I would like to figure out how to accept my situation and move on. How do I accept that I will be alone for the rest of my life?

First, you don’t have to be alone for the rest of your life, unless that is what you truly want. Believe it or not, there are people out there who will love you for the true you.

You are not your body. You are not your looks.

 I’m proud of you for taking a hard look in the mirror and accepting the truth of how difficult romantic relationships are for you. That is not easy! It seems that a lot of what hinders you are factors that are out of your control.

You have allowed yourself to move on with what you have and who you are physically. Now, it is time to decide what you want from life.

You don’t want to be alone! You need to stop saving yourself from possible disappointment or rejection.

If you decide to accept being alone for the rest of your life, you’re simply giving up. You need to find your self-worth and confidence in who you truly are. Love yourself enough to move past this. You are just wrong if you think love is out of your reach because of your physical makeup. Just like people that think aliens aren’t real…we can’t prove it yet, but the numbers say the probability is virtually guaranteed. I think your chances of finding a happy, rewarding relationship are virtually guaranteed too, but you must be realistic, honest, positive, and confident.

 I understand saying “be confident” is much easier than actually doing it, but fake it until you make it. If you stop portraying your body as who you are, potential lady suitors will follow your lead.

She is out there. Maybe she is an inch shorter or wider, maybe she loves coffee and you despise it, maybe she is blonde and you only wanted to love a brunette… I do not know. The point is, your way of thinking is part of the problem.

YOU DESERVE LOVE just like everyone else and there is a someone special out there meant just for you, you should make an enormous effort to find her.

Finding love isn’t easy, but you still have to try.

You have to put yourself out there knowing you could get hurt time and time again… until eventually, you don’t. This is just how it works.

Work on your appearance. Stay in shape. Maybe, if finances allow, invest in an image consultant who can help with your overall style. Don’t wear platforms in your shoes or doing anything misleading or extreme.


When it comes to the bedroom, make use of toys and everything else on your body. Become a damn “spider monkey” in bed. Learn things she has never heard of and surprise the hell out of her. She will remember your penis is smaller than she would like perhaps, sure. She will also remember the crazy, freaky, new, exciting sexual experience you gave her that no one else ever has. Satisfying your lover in the bedroom doesn’t solely rely on penis size, never has. Some women can’t climax from intercourse alone in the first place.

For now, get your attitude right and think only confident thoughts. Never consider quitting or being alone. Focus only on presenting your best self.

Chin up! You have work to do!

P.S. I never do this on JAM, but I suggest using my workbook to help you analyze who may be a great match for you. Here is a link to the workbook. Click Here


Top Ten Reasons People End Relationships

  1. They don’t feel appreciated
  2. Infidelity
  3. Financial incompatibility
  4. Lack of communication
  5. Lack of effort
  6. Major life event
  7. Boredom
  8. Lack of met expectation
  9. As you grow, you do it separately, therefore growing apart
  10. There was no real foundation in the first place

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.

My Marriage Needs its Sex Back!

Reader’s Question:

 My wife and I are in a sexless marriage. It has been about a year since we were intimate and things get awkward with us physically. We don’t really kiss or touch and when we do, it feels like there is a major disconnect, and talking about it gets us nowhere. I know my wife well and this isn’t about an affair or something like that. Life and kids have taken its toll on our marriage and I need to fix it. Please, any advice you can give me to help me talk to my wife would be appreciated.

I hear this all the time. Your situation is more common than you think, but you really have to make an effort to turn things around.

Raising children is hard on a marriage. Life’s ups and downs are hard on a marriage. Marriage is hard work, period.

There will be times when you look at your spouse and think, who the hell are you and why am I with you. Other times you will look at them and think, I’m the luckiest person in the world.

You just have to ride the waves.

It is time to have a serious talk with your wife. Things need to change. You two need to reconnect. Start with an open and honest conversation. This is not the time to blame. It’s a time to listen and learn.

The last thing you want to do is make her feel that this is all her fault.

I have worked with several couples over the last decade that have gone through the same issues. One wife came to me and explained it has been two years, six months, and three days. She was driving herself insane. It was ruining her marriage. She thought her husband was cheating or wanted a divorce, but was too afraid to ask for it.

He wasn’t cheating and he did not want a divorce. They had twin boys and both worked full-time. Life is what was happening.

We often forget to make time for our marriage. Having a family dinner together is not husband and wife time…it is family time. Spouses should schedule time together on a regular basis. Having a planned “date” is a huge psychological motivator to get through a hard week. If you work full time and have two kids, then every week is a hard week, that would benefit from a little “light at the end of the tunnel.”

Making time for the two of you, separate from anyone else, should lead to more sex and a stronger overall connection.

When was the last time you and your wife made time just for each other, on a regular basis? Even if you only have an hour a week and a few bucks to your name, you can still make it happen.

Put the kids to bed, go lay in the back yard, and just watch the stars…or whatever…you get the point.


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