The Advice Column – A Dating Question About a Guy Who Wants to Date a Girl


What readers want more than anything – is advice.  Each week, I receive a number of questions.  Most of the time I provide these answers specifically to the inquirer, but it appears much more helpful to put these answers here, so you can benefit from them too.

If you’d like to check out last week’s question.  Click HERE.

Today we answer the second question for The Advice Column.


“I have a dating question for you.  I am a guy in my mid 30’s.  I want to date a girl who is a bit older than I am.  She has a child who is already grown up and out of the house and is recently divorced.  I want kids – big time.  She might not be open to having more kids.  Do I forget the whole idea? Please advise.”


“Thank you for this great question.  It’s complex and the many moving parts are valuable to look into.

First of all, let me commend you for knowing what you want.  You want kids and this is wonderful.  As someone who is expecting my first child, there have been very few experiences that have been so beautiful than the anticipation of new life.

As this question is comprised of many concepts, not all are simple – so due to the complexity of the question, it’s good to break the various concepts down into bite-sized pieces.

Concept #1 – Dating

People hate dating.  Why?  It’s tricky.

Combining people skills with developing a new friendship, coupled with fears of rejection and lowering walls that have kept you safe – it’s intimate and scary.  There is a lot of risk involved.  However, just because it’s risky, doesn’t mean it’s worth hating.

Hating dating is a waste of energy. (Yes, you can tweet that.)

I’d like to present dating in a fun, fresh way.  Try this…

“Dating is fun.”

Try not to put any pressure on yourself or on the date.  You’re getting to know someone.  New relationships are fragile, it doesn’t matter what type of relationship it is – coworker, friend, acquaintance, client, etc.

Find your strength-zone and relax into it.

What’s your strength zone?  Liking who you are, being happy with that person.  When you are happy with yourself then the outcome matters less.  If you don’t like yourself – honestly, you have no business dating.

Concept #2 – Age

As someone who married a great guy much older than myself, I do believe that age is not a factor (so long as everyone is over 18 and of sound mind).  The key is to ensure you have enough in common and solid foundational values.

I’ve dated many, many people who were older than myself and it was difficult to stay connected because we didn’t have enough in common.  That being said, it’s important not to count someone out just because they might seem older.

My husband has enough energy to run circles around me and keep me on my toes.  Age hasn’t played a factor because our values and many interests are in alignment.

Concept #3 – Kids

If she hasn’t told you she isn’t willing to have kids, don’t assume she isn’t willing.  The fact she has a grown child is kind of neat.  Is it a person you respect and enjoy?  Experience can be great.

That being said, if she doesn’t want to have kids, then dating her will be a waste of time because your future will be incompatible.  This is nothing one quick dinner wouldn’t resolve.  Be sure to ask, “Where do you see yourself in 5 years?”

If she definitely is not open to kids, don’t be afraid to leave.  Once in a very happy relationship, my boyfriend and I didn’t want the same 5 year plan.  Even though it was heart-breaking, the right decision for me was to leave.

Even if I never had children, I wanted the option.  I wanted the possibility.  It’s not fair to resent someone for not giving you the future you want if they are brave enough to tell you where they stand.

Concept #4 – Divorce

Of all of the factors, this one is somewhat of a red flag.  I have a lot of questions.

How long ago was she divorced?  Did they separate first?  Was is a peaceful divorce or were there difficulties?  How did the divorce impact her financial situation?  How long was she married?  How many times has she been married?

If it’s been over a year since the divorce and she has taken some time to work with a counselor or coach and work on herself, that’s a good sign.  People coming out of divorces are in a significant amount of pain.  They will sometimes try to bury the pain of their loss (divorce is a big loss – it’s the death of a dream) in the next relationship.  Things an surface that are difficult for everyone.  I would not consider getting into a relationship with someone in that stage of life – let alone having a family with them.

If it is someone you enjoy, it’s worth pursuing a friendship until the kinks have been worked out.

As I am a fan of dating lots and lots of people while you are choosing a life partner, I don’t see any harm with a few dates a getting some of the answers to those above questions.

With more information, you can make a solid, awesome decision.”

What else would you suggest for the inquirer of this question?





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