How to Make a May-December Romance Last For More than a Season

I have always had a certain predilection for older men.  That is not to say that I have exclusively sought out older men, but I have never turned down an opportunity when one arose.  I’ve dated men as much as 30 years older than I and learned some important lessons along the way.

Now, there is no magic formula to making a romance with an older man or woman work, but there are a couple things will greatly increase the chances of having this kind of unconventional relationship successful and long lasting.  In my personal experience, the MUST HAVES in a May-December love are comfort level and compatibility.

Comfort level in a relationship with a significant age gap is vital.  People who are easily embarrassed should really consider if this kind of relationship is for them.  If you can’t stand people staring, asking questions or making assumptions-out loud-about the nature or validity or appropriateness of your relationship…well, you probably won’t fair well in your relationship.   When you go out in public, you must be confident enough in your relationship to allow some things to just slide.  You have to expect people to treat your relationship as a joke or mistake or a symptom of a midlife crisis.

CASE IN POINT:  my husband and I boast a 20 year age difference.  We have 2 young children, and people very often “mistake” him for the grandfather (sometimes on purpose).  For my part, I’ve had women his age absolutely disrespect me–surely this man is not messing around with this young girl?–by flirting outrageously with him while I’m standing there.  I’ve also had men closer to me in age walk up to us at dinner and ask for my phone number.  When we first starting hanging out, I would get really offended.  Now, I barely notice and when I do I make sure that they know that our relationship is not a game.  It is what it is, and we like it that way.  And in order for your relationship to really take wings and fly, you both have to be smooth with the notion of people getting in your business, and strong enough to get them right back out.

Comfort, though exceedingly important, is nothing without compatibility.  It may sound asinine, but you HAVE to ask the question: Are you compatible?  You must have commonalities in order for the relationship to prosper rather than fester.  One deadly strike to any relationship is a lack of common interests–this actuality doubles when you factor in an age gap.  Shared pursuits determine so much: where you spend you time, how you spend your time and with whom you spend your time as a couple.  If all of your activities are age-related (i.e. everything you do centers around your same-aged friends as opposed to your friends centering around everything you do), then a May-December romance will not workIt will die quickly.

My husband and I spend nearly all of our free time together.  This is made possible because we have always enjoyed the same things:  travel, new cuisines, jazz, HGTV, people watching, our (four) children…we have been together for 8 years now because we enjoy each others company and doing the same things.   Our friends and acquaintances actually share those same pursuits.  The age of our friends varies–usually a nice average of our ages, believe it or not!  But that blessing has come from focusing on our commonalities outside of sex.

This by no means wraps up all of the ins and outs of dating someone significantly older/younger than you. However for your relationship to even stand a chance when it comes to your family weighing in, your old friends having their say and the world in general looking at you a little funny, you have to at least be comfortable with the realistic struggles of dating a different generation and be compatible past the bedroom.  I would encourage anyone to try it at least once.  You may be surprised at how things turn out.


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