Dating After Divorce For Men: Getting Back In The Game

Part One of my “Back on the Scene: Dating the Second Time Around” I will cover everything the recently divorced man needs to know when getting back in “The Game”.

You haven’t dated for a while. Perhaps you’ve recently left a marriage or long-term relationship.  You might ask yourself, is it the right time to face a whole new world ?  Certainly things have changed, at least that’s what we second-time around daters hear from friends in our situation. After a good while off the market, the dating game can easily intimidate even the most confident.

To start off, this guide is geared toward the 30 to 50-something guy who is ready to jump in or at least willing to test the waters after being outside of the dating world for some time.  It also assumes the reader is dating with the intention of ultimately starting a new relationship.

Generational Differences

Our generation is sandwiched between two that have completely different rules. Blurred roles and unclear rules add a level of ambiguity the generation before and the one after us have never had to manage. In our age-group, acceptable behavior and etiquette differ depending on whom you ask. If you rely on others’ advice, you may walk away more confused than ever.

Our parents’ and grandparents’ generations knew exactly what to expect, what appropriate dating behavior looked like. Typically, young people dated with the intention of finding a husband or wife.  Nowadays, we meet up with the opposite sex (or of the same, which is yet another change that has become more socially acceptable in our time).  In the “good old days” the guy asked the girl out, met her parents, and paid for the date.

For those of the younger generation, if I can trust my teenager’s report, no one frets about who takes which position in the dating dance.  Apparently, for the Millennials, it’s perfectly appropriate for a girl to ask out a guy.

Role Changes

In the last few years I have observed these role changes by seeing my daughter attend homecoming and the prom with a group of her friends instead of with a date.  None of the girls had dates. To make sure my child wasn’t suffering from social ineptness, I verified with other mothers this is now a common practice among high-schoolers.

I see our generation as one that, at times, must muddle through some muddy water to find a real catch.  Some questions that come to mind may be: Will you score points by opening a door and pulling out a chair?  (Hint: yes).  Who pays for dates?  Who initiates the asking-out? Should you try to kiss her on the first date?

Admittedly its an unfair double standard, but I can assure you the grand majority of women expect to be treated with at least a minimal level of chivalry while at the same time enjoying an egalitarian relationship. But if you consider reality, both genders have to deal with double standards in one form of the other.


For those those of us dating the second time around, there are some common challenges we have to face- competing responsibilities and stressors. Some of these include exes, kids, and financial responsibilities.

More than once I’ve heard a guy respond to a question with, “That’s a long story.”  Well, from my point of view we all have one or more “long stories”.  Unresolved issues, baggage, or however you refer to it – we all carry some to varying degrees. It’s not whether we have it, but how we deal with it; and how we deal with it can make or break the possibility of starting a great relationship.

Generally, men tend to begin dating fairly quickly after a significant relationship ends; whereas women take their time, reflecting on the loss and recovering. For this reason, when men enter the dating scene they may be juggling unresolved stressors from the recently ended relationship. This doesn’t preclude the ability to find the right person, but the stressors need to be handled well.

First Impressions

You know what they say about first impressions. You can only make one.

While women aren’t as visual as men, we certainly care about your appearance, just as you care about ours.  Your self-care and the time you take to keep yourself groomed and clean does not go unnoticed.  It communicates a certain level of self-respect. At the same time, we are realistic in that most of us don’t expect to meet Brad Pitt’s doppelganger.

Physical Appearance and Health

Two key points that work in your favor are that women our age are more realistic than our younger counterparts.  Just like you, we are no longer at our peaks in terms of physical shape, so we will accept some leeway in terms of physical appearance.  We accept our aging and understand the same in a potential partner.

This is not to say, however, that we don’t appreciate a man who cares about his healthy and appearance.  In fact, you may not be where you’d like in term of physical shape but the interest in self-care and health is a big plus.

It does come down to simple attraction, but also says something about a potential partner’s level of self-respect. Sharing that you have joined a gym, are looking for an activity you enjoy to get into shape, or that you have health-related goals you plan to reach can be enough for us to take notice.

While you may not be where you want in terms of physical health and appearance, you can actively work on this while out there dating.  It can prove to be a great point of conversation to communicate that your health is important, thus you are actively engaged in some type of exercise program; AND maybe doing something active together could be an opportunity for a fun date.

Maybe you have no interest in or intention of getting into shape.  I hope you would reconsider, not just for making a great impression but for your own well-being; however if you are stubbornly against this idea, all is not necessarily lost.  You aren’t necessarily doomed to be single.  Some women like the teddy bear type.


You probably are due for a wardrobe update.  That doesn’t mean you have to spend a ton of money to replace every piece of clothing you own, but make the investment in a few articles of clothing that flatter your physique and overall physical appearance.  Showing up for dates in your favorite t-shirt with worn, fraying collars is unacceptable. If you aren’t adept at fashion, run your new clothing options by a sister, friend, or co-worker.  Have them look for ideas online to give you an idea what would appeal to women.


Make sure you are clean-shaven or have tidied up a goatee or beard.  A fresh haircut and a little cologne can go a long way.  Do you realize the fragrance industry brings in $$$ per year and we women are the ones buying it for you?! In actuality we aren’t buying it for you; we’re actually buying it for us.

Cologne is a natural aphrodisiac.  So wear it, but sparingly.  Bathing in the stuff will have the opposite effect.

Perhaps you gentlemen are unaware, but when we women meet someone we like and it’s clear things will be progressing, we following the unofficial girl rule of improving our panty supply with sexier versions of the usual.  It’s only fair you consider the same!

Take an inventory of your clothing, including things like shoes and belts.  Are they worn? Check out your hair cut and facial hair.  Take a whiff of your armpits.

If you feel clueless, find solace in the fact, you aren’t alone. In the next part of my guide well talk about online dating, click here to read it and What Women Want.

Notice: is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program. earns fees from products sold through qualifying purchases by linking to Amazon offers a commission on products sold through their affiliate links.