Falling in Love Again: Dating Tips for Mature Adults

For adults who are not in a relationship, Valentine’s Day can feel like Christmas without a family to go home to.  If you are unexpectedly single in later life, know that the need for companionship and desire for romance never goes away.  Since we live longer and healthier lives, the opportunity always exists to fall in love all over again.

And yet, most singles will admit that the dating learning curve can be treacherous.  To begin with, the experience of dating later on in life is significantly different than dating in your twenties – you are more cautious, more vulnerable to rejection, and the script no longer includes a house in the suburbs with 2 kids. We are beyond the biological imperative of coupling and now the field is wide open for creating an adult relationship that is unique from your younger years.  And that’s scary.

What is needed is a framework that clarifies behaviours for men and women from the first date, through the development of a healthy man-woman thing, to the point of a lasting commitment.

Let’s start by introducing the five stages of dating:

  1. Attraction

  2. Uncertainty

  3. Exclusivity

  4. Intimacy

  5. Committed

Here we’ll talk about dating behaviours in the Attraction phase (more in later blogs) to warm us up for Valentine’s Day.

Attraction is all about sustaining the magic while you are getting to know someone.  This means that you need to express your best and most positive self.


1. Take me as I am or not at all.

One of the biggest challenges at the beginning of a relationship is to sustain feelings of attraction while we are getting to know someone. We need to be aware of how our behaviours may be interpreted by the opposite gender.

In my conversations with women about dating I often hear something like, “He should take me as I am or not at all.”  OK. No. Getting to know someone that you are attracted to must be done gradually over time.  Putting it all out there right away feels like too much information.

2. Stop interviewing your date for the position of husband.

A common misunderstanding women have of men is that they communicate like women. Girlfriends take turns talking, then asking questions and listening. We make the mistake of assuming that the more we listen to a man with great interest, the more he will be interested in us. Unfortunately, on their planet, the more a man talks, the more he becomes interested in what he is talking about.

In order for a man to be interested in a woman, she needs to do more of the talking and share herself in a positive manner. Stop with the questions!  And for sure stop with the questions that sound like you’re interviewing for the position of husband.


1.  Take the time to ask questions, listen and get to know your date instead of talking about yourself and offering advice.

Have you ever been in a café and observed a couple on a first date?  The man is happily talking about his work or theories on life.  He thinks that he is impressing her because she keeps asking questions and he naturally believes this is what she wants.  When she does get a word in, he mistakenly assumes that she is asking for advice and begins offering solutions to her problems or answers to her questions.

It’s easy to see that while the woman is politely listening and nodding, she is bored. This man is turning her off and has no idea why.

This man needs to ask some questions and show an interest in getting to know his date.  Guys, try some open questions like:

2.  Do something to make a woman feel special and in her eyes you are more attractive.

Notice her, give her a sincere complement, or initiate eye contact.  Where you can offer these gestures without being dependent on getting anything else other than the pleasure of getting to know her, you will become more attractive.

So this Valentine’s day, get out there and flirt.  Put your best self forward and see who shows up in your life.  Stay tuned for our next blog on Phase 2 of Dating: Uncertainty.

Karen Brill

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