Should Rebound Bachelor Marry Rich Woman

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September 30, 2014
I stumbled on your site the other day, and have been enjoying it ever since.  I read the articles here on regarding the 14 different types of women, and need some advice.  I am 46, and have been divorced for a year now.  I have a 10 year old boy from my marriage, as well.  I started dated soon after my divorce as I had been missing physical and emotional intimacy for many years.  The reason for this is my wife turned out to be lesbian, and had no attraction or interest in men.  Once I discovered this, it all made sense, and I made the decision to move on and find someone who would appreciate and enjoy a man.

I dated a lot, and had sex with a few sex-craved women.  I don’t have too much trouble dating, and I look younger than I am.  Anyway, I started dating a woman that I met 5 years ago, but we were both married at the time.  We had kept in touch, and things finally fell into place.  We have fallen in love with each other, and she treats my boy great, and he enjoys her company, as well.  I am scared as she wants to move in together, and have a baby.  I am happy when I am with her, but she makes my life hell when we are not together.  I’m not sure why, but her mind creates drama and she blames me for her feelings.  I would say, based on your 14 types, that she is a Boss, Showgirl, and Nymphomaniac.  I find myself questioning if she is right for me, and that I am getting in too deep, too soon.  I don’t like being alone, and definitely enjoy her company.  The sex is off the charts.  She is petite, beautiful, takes lap dance classes for me, Filipino, kind hearted, 8 years younger than me, and wealthy beyond belief – yes.  She is a CEO, and makes over a million dollar a year.  People tell me that I hit the jackpot, and if it weren’t for the roller coaster ride of emotions she puts me through (she is never wrong and blames me for everything), I would agree.  She is wanting to buy a million dollar home, and start a family.  I’m scared, but I don’t want to screw this up.  How should I deal with it?  Is the money issue that important?  I have always been the one to support the family, so this is new territory for me.

We are at a standstill right now because I have told her I don’t want to get married, and have any more kids.  She claims that I have misled her as she has expressed her needs for a baby, and to be married.  I explained to her that she assumed I wanted the same, but she never actually asked until last night.  She wants to adopt a little girl, and I support her in that.  Last night she mentioned a prenuptial agreement as a requirement, so at least that is a start.  Maybe if she adopts first, before any kind of marriage, that would relieve me of any legal obligations down the road.  She tested me earlier today and asked me when I would like the key to my apartment back.  I said, “whenever it is convenient for you”.  I must have passed the test because she is on her way here to give me a BJ to make me feel better.  LOL.


First of all – thanks for writing in.  I have to tell you – you are recovering marvelously from the ordeal of your wife turning out to be lesbian.  That must have been a very difficult thing to go through.  I’ve actually seen that many times before here – but it was the husband who “became” gay – there is an article about this here on midlifebachelor:

Five Signs Your Husband May Be Realizing He is Gay

So congratulations on being able to successfully shake off that traumatizing ordeal, and moving forward with your life.

Here are a few observations.  There is some chance that you are ON THE REBOUND … which his essentially a fear of being single or by yourself.  I discuss that at length in a different article here:

On the Rebound – Does Fear of Being Single Drive Your Behavior?

So you might check that out, when you have time – and just be aware of the symptoms.  They may or may not apply to you.

Now – with respect to your actual request for advice about what to do with this crazy but wealthy Filipina woman … let’s analyze the situation here.  First of all – you are almost correct about the different Types of Woman she is (according to my article here – The 14 Types of Women)  As you correctly noted, she is a Boss (likes to boss you around), a Showgirl (drama queen – always putting on a show), a Nymphomaniac (because she is always jumping you) … but the one you missed is a crucial one … she is a Jackpot (because she is a high income earner, and can support you financially, if necessary).  Her being a Jackpot changes everything – because serious money can compensate for many other deficiencies.

Want to meet and date a wealthy man or woman?  Please see a related article here on entitled, How to Meet and Date a Wealth Man or Woman

Here are some things for you to consider:

1)  Marriage is an inherently flawed institution.
Marriage is the #1 cause of divorce … so if you get married, be ready to be divorced one day … because odds are it will happen.  Some people (myself included) think that marriage is a portal into hell … meaning that going there can seriously adversely affect your own happiness in the long-term.  May or may not turn out that way – but just be mentally prepared to go through another divorce again (but for very different reasons versus your last divorce, obviously).

2)  She is rich – she can take care of you financially.

This is a tremendous reason to continue the relationship … possibly even to marry her … because YOU might be the one receiving alimony someday.  Just a thought – you might just do it for the rest of us midlife bachelors (so we can cheer you on).  I’ve personally never dated a woman who had more money than me – but I would in a heartbeat.  I would treat her like gold – and I’d probably put up with a lot, especially if she was hot.  Just something to consider!

3)  One word of caution – before you marry her, be certain about her financial condition and potential liabilities.
Very wealthy people are subject to the same missteps as everyone else – and have the potential to have very large liabilities.  In other words, a normal person might be in debt for $400,000.  A very wealthy person might be in debt for $4M.  If she makes $1M/year – that’s nice … but how is that $1M/year relative to what she owes?  Are there any current or upcoming liabilities on her part that could potentially drag you down in the future?  Just be careful – and perform your own due diligence!

4)  Anything that bothers you A LITTLE right now … will eventually wind up bothering you A LOT later on.
Just saying. Only you know if you can handle it – or not.  This is true with any new relationship – whether you marry her, or not.

5)  Enjoy that crazy sex – that is a unique gift that rarely happens.
Enjoy it like hell until you cannot continue with the relationship – for whatever reason.  You must be grateful for this incredible gift or find that you have right now.  Don’t waste any time – go and hit it again right now, Brother!

Now do I think you should marry her?  Only you know the answer to that – but from what I’m hearing from you, it sounds like it is just too soon to remarry since your last divorce.  I suggest a strategy of DELAY … tell her you just need a little more time … because you just got divorced … and you really need to go through a phase of self-healing and introspect before you commit yourself so totally to her.  If she doesn’t buy into that, tell her that after you’ve gone through this introspect phase, you should then be ready to commit for life.  If she asks for a time – how long … tell her you don’t know … you cannot rush mental healing … you cannot rush nature.  That would like telling a wild animal to hurry up and do something … it’s just wrong.  ha ha

Okay – I hope this was helpful.  I would like you to consider joining our Midlife Dating Forum.  Here is a link – Midlife Dating Forum.  We have many people there in their 30s/40s/50s in similar situations … divorced after long, imprisoning, suffocating marriages or relationships … who support one another and bounce ideas off of one another.  We would be happy to have you join our group.  Good luck – please report back with what happens!

Anyone who wishes can also add a COMMENT to this article directly below, in the COMMENT section.

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About the Author

Midlife Bachelor chronicles lifestyle, dating, and relationship experiences and advice to avoid a midlife crisis. Readers like you are often beyond young adulthood in their 30’s, 40’s, and 50’s that want to understand how dating, sex, relationships, and love fit in with our lifestyles.