What is more challenging than weight loss? More difficult than Algebra? More frightening than facing a three-headed monster? Why, dating over the age of 40 of course.

For some people the above analogies might not apply, but I suspect for many of us restarting our dating lives after a long period of dormancy the aforementioned is the truth. I’m no different. For the record – dating sucks when you’re a full grown man.

A plethora of problems come to mind when dating over the age 40.

1)      Exactly how much money will I need and am I the only one paying? Dating is not for the poor – although there are a number of things you can do for free but most women will only tolerate free dates for so long. Bringing over a six-pack, a bottle of cheap Moscato, and a large pizza just won’t cut it. Eventually you have to show your worth.

2)      How many dates can I pursue during a given week? The short answer is as many as I want! Of course keeping in mind Issue #1. Additionally, the stress of work, kids, washing my socks, etc. proves that it is no easy task to go on dates nightly. This cuts the dating time down to a few times a month if I’m lucky. Choose wisely.

3)      What? No sex on the first date? When did this trend start? I must have missed the memo since my college days when everyone seemed so wild and carefree. There was a time men talked about other men “sowing their oats” and gave the obligatory wink of approval. However, today we are living in an age of incurable disease and changing lifestyle which forces our hands of morality when choosing sex partners. The choice is not always about volume but sharing an intimate moment with someone special.

4)      My kids. Yes, paying attention to your kids is going to cut into your dating life. Not only from a time management standpoint but emotionally as well. I don’t mind having this type of problem; however, women over a certain age typically have older kids therefore making it harder for them to play second fiddle. I will caution women that if you have a man doing what he can to take care of his kids he’s probably a keeper. IJS

5)      Choices, choices, and more choices. I thought my high school and college years were full of choices. There seems to be so many single people roaming this free country of ours that the stable is endless. With so many choices can a man really expect to rush through the dating life? Granted, everyone’s choices are not the same but we all have them regardless. Dating is not just about quantity as first gleamed.

6)      A lack of desire for love. I often hear women say they married for love the first time and the second time for money. What say a man? I married for sex the first time and will marry for sex again? Not quite. The difference – there will be no second marriage. At least those are my thoughts initially and presumably shared by many a man. It takes careful introspection to determine who I am now and what I desire for my future. Time heals all wounds.

As you can see the issues mount up quickly. Now do note – I am not against dating, marriage, love, emotional slavery, Valentine’s Day, etc., but I will approach dating cautiously. Society’s approach to dating when young was to be more cavalier and it worked fine as we experienced life as young adults. But there are so many other responsibilities that arise when you age that they can’t be ignored. We all want someone to share special moments with but we all are very guarded more than before. All hope is not lost as we see people fall in love every day regardless of age. And that, my friends, is a good thing – hope.

Man of Wisdom