In Between May and December: 4 Steps To Maintaining Your May-December Romance

We romanticize young women being swept off their feet by dashing older men. The Sean Connerys and Pierce Brosnans and George Clooneys and Michael Jordans of the world have their pick of gorgeous dewey eyed young ladies. We swoon, humming someday my prince will come–and hoping against hope that he won’t be a douchebag our age, but an older, well travelled, most interesting man in the world. He will teach us. He will lead us on adventures. And he will do it from his well established perch atop success.

Reality is this: he is still a man–and a man who wants a younger woman for more reasons than just love. Your naivety alone pays for the privilege of living underneath the shadow of his silvery wings (hair wings that is). If you look good, smell good, act good, and try good, then you are a perfect fit for the complexities that lead a growner than grown man to–sorry to hurt your feelings–trade down to a baby girl, sex kitten though you may be.

Until you start to grow up.

Many of us with self esteem issues (daddy issues in particular) prefer older men because older men baby us and protect us and coddle us. But as we actually grow into ourselves, the role of “big daddy” no longer fits. Try as we might to struggle back into our old role, it won’t work AND you be happy, too.

But take heart! There are some things that you can do to ease the transition from being baby girl to natural woman.

1. Be aware. You need to know when you are being treated like a child so that you can stop responding like one. Men always prefer power and position, and it is a natural inclination for a man of a certain age to lump you in with his (possibly) grown kids. In these situations, you do not need to be dramatic; you just need to calmly remind him that you not one of his children.

2. Be self sufficient. You NEVER give over complete financial control. NEVER. That is a recipe for longterm disaster. He will begin to treat you like an object that he has purchased instead of a human being. Men are careless with things that depreciate with age and use, soooo… I don’t need to spell out the fact he has already objectified you a little bit to make the transition from women his age to one who wasn’t born yet when he was a freshman in high school.

3. Be Honest. I met my “old man” when I was 23. I barely knew my own name–let ALONE what I might be like 12 years later! It took great personal upheaval for me to honestly say, “That girl is gone. I am a grown woman now”. Everything about me has evolved in some way, and it will for you too. Prepare yourself to have the inevitable “You’re not the same” conversation that he will want to have multiple times to help him decide to stay or go. . Be kind but again: firm.

4. Be Prepared. He might not like you as an adult. Are you prepared to part ways? Are you emotionally ready to stand your ground? He will miss the old days, the old you. He will want your hair to be straight again, your heels to be high, your sex to be gymnast quality. He will want the tickle and giggle that made him take the leap. He will most assuredly fight for the person he knew. You must be equally prepared to fight for the person you now are.

I am no relationship expert; I do have experience dating older guys though. And if you are in it for the long haul, I want you to have the tools thar I have had to create along the way.


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