As a child, I loved when the holiday season approached– starting in November, New York City would transform into a spectacular place with all the streets adorned with wreaths, lights, and beautiful bows.  Walking along Fifth Avenue with my mom, I was mesmerized by the store displays, which were almost magical, and the tree at Rockefeller Center was truly a sight to behold with all the ice skaters gracefully whizzing around below while the sweet smell of roasted nuts filled the air.  These are the memories I cherish from the holidays during my first two decades here on Earth.

As an adult, however, things became a bit more complicated, and over the years I’ve come to realize that I am definitely not alone, as families everywhere grapple with these three key questions:

1. Where will we be for the holidays?
2. Who will we be with?
3. How much will we spend?

If you are all on the same page with the answers to these three questions, consider yourself incredibly fortunate.  Unfortunately, many are not– and for some couples, it is the perfect storm that can force them to face some divisive issues, which ultimately may cause them to part ways.  If this doesn’t make any sense, let me explain.

Where to spend the holidays– Some people do not get much time off work or from school during the year, so the holidays is the perfect time to travel.  But not everyone likes to travel, and then there are those that want to use that time to explore sights unseen whereas others just want to travel to see their families.  So here we have a very simple and completely understandable conflict of interest, but not everyone is able to handle conflict well, and many become entrenched in a battle of wills where no one is willing to concede or find a compromise.

Who to see during the holidays– When you are in a committed relationship, sooner or later you will face the question of which family to visit.  It will not always work to divide and conquer, so then when do you spend time with your partners’ family vs. your own if it’s not possible to accommodate everyone at once?  Are you willing to alternate? This may not be so easy to answer when you really don’t get along with the other person’s family, or if travel costs are significant.

How much to spend over the holidays– Money talks are never easy, but it is particularly difficult when you don’t see eye to eye on a discretionary expense (versus a necessary budget item) such as gifts or travel, because there are a lot of deep-seeded emotions and value-judgments that come into play here.  What one person may consider overly generous, another may consider stingy.  If you are already on a tight budget, a person that is more prone to saving is definitely going to be on edge if other family members are not sensitive to this very real need for that person’s need to have financial security.

Ever since college, I admit that I have routinely struggled with such seemingly simple questions- where will I spend the holidays, with whom, and how much can I spend?  To be perfectly candid, the answers have varied throughout the years depending on the circumstances of that time, and when I was married, finding a compromise that worked for everyone was never easy.  On my own, it is definitely much easier to make the choices that I am most comfortable with, but even now there are competing interests and family dynamics to take into account.

So, if you feel like you are being hit with the perfect storm this holiday season, at least know that you are definitely in good company and for good reason.  It is simply impossible to please everyone– especially during the holidays– and we all have limited resources in terms of time, money and energy, which are all at play this time of year.  Hopefully, you will find a way to do what works best for you.


By Regina A. DeMeo, Esq.