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Dating at Midlife/Money Issues in Relationship


Hi April,

I am a single mom in my early 40s and have been dating a single dad in his late 40s for a year.  Our relationship is fantastic, we are committed, in love, our communication is great, and our kids all get along really well.  

At this point, I am not considering moving in with him.  But that will be a conversation we will probably have short to mid-term as we are serious.

Here is the problem.  He has told me many times he is not good with money.  He tends to spend too much and would really like to change that.  He makes a good salary, owns a house and takes care of his 2 children (shared custody) wonderfully.  A few days ago he asked me if I could help him with his budget.  I must admit this is one of my strenght. My children primarily reside with me so I am responsible for all their expenses. I also own a house.  My budget is balance and we live well.

My boyfriend, a very smart, organized and professional man, has a budget worse than I could imagine.... It does not balance at all: his estimated expenses exceed his revenus by almost $2000 a month!!  I don't understand how he could not have known this...

This now has me worried... how can I help him through this?  Do I want to get involved seriously with someone in a bad financial situation?  We are leaving on a family trip this summer... I know he will pay his fair share (if not more, he is very generous...) but he really can't afford it!

I know money can become a real issue in a relationship.  But everything else works so well!  Can I be optimistic that we will get through this issue also or am I being too naive?

Hi Kate,

You show your relationship maturity well by asking this dating question.  Indeed, money can be quite an issue for couples, and as we age and mature, it only becomes more so.  Mature singles definitely need to consider and openly discuss finances before making a lasting relationship commitment.

I have to ask because it is such a glaring financial issue.  His expenses exceed his monthly income by about $2000 each month?  If that is so, does that mean somehow he is accruing $24,000 of debt each year?  Perhaps his income has a variability like a quarterly bonus that covers it all each quarter?

Since the two of you have been courting for about a year now and you are both mature people, please read, you're not just young and naive in your twenties, then you two really can have some mature discussions about this.  How does he cover that excess $2000 per month?  And if he does have a debt build up, then will he do what is necessary for 6 months, 12 months, 2 years, to pay that down and off completely?  Will he live within his budget?  Would he be open to your creating a livable monthly budget for him?  

And then reflect for yourself.  Is his income and lifestyle potentially in harmony with yours?  Do you earn substantially more than he does?  

His 2 children, are they in college where he will be wrapping up his financial support of them sometime soon?  Or are they in middle school or high school such that his financial support will necessarily continue for quite some time?

And then discuss the family trip just like you would if you two were married.  Can we actually afford to do this together?  If not, what is more appropriate for his budget and means?  Can you do then dial back the trip to enjoy a vacation which is better suited for the financial means you both have?

I don't think you are being too naive at all.  Don't be too optimistic either.  Face the issue with maturity and open communication without judgment.  Share with him your feelings of being concerned.  Treat yourselves with dignity and respect and open the door to relationship building by openly discussing finances.  It is always emotionally loaded.  

Then by all means, let me know here how it goes!  

Dating at Midlife

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April Braswell - Dating Expert


Can certainly address the romantic questions from Boomers looking to date again after divorce or the death of their spouse. Address how dating and courtship principles remain the same, however many of the tactics are different now. How to use social media and online dating sites well which reflect your age and style, not that of your grandchildren.


As seen in Dating for Dummies, 3rd edition. I'm an internationally recognized Dating and Relationship expert, frequently on Radio and serve as "In Touch Weekly"'s go to relationship expert for questions regarding celebrity couple relationships. Additionally recognized for specifically serving the different romantic needs of the Baby Boomer generation, having contributed to such media as Gateway Media, Woman's World, and The Boston Globe.

As seen in Dating for Dummies, 3rd edition.

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