Second Act Dating: Shopping For A Man

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A few weeks ago, while having coffee with a married friend, a beautiful and lust-worthy man crossed our path. We turned our heads and watched as he ordered a double expresso and bagel. I stared at his overall handsomeness while my friend’s mouth hung open and she lost consciousness of the world around her. I couldn’t ignore the change in her demeanor. After the man was gone, I spoke my mind.

“Do you really want to be with the same penis forever?” Before she could answer, I pumped out a few additional questions. “What if you could go shopping for a new one? A long one? A thicker one? One that hung left or hung right? One of a different color?  A younger one? An older one?” I was on a roll. “With so many options available, if you could, would you?”

In the end, the risk-reward to my coupled girlfriend was not worth it, and far different than the risk-reward to the single girl, aka me. Is being single versus being married the equivalent of a ‘we guarantee all purchases return policy’ versus a ‘no-return final sale policy’? For single me it’s like shopping for a new prom dress. Some stores give you the ability to look, try it on, or take it home, before you decide if you want to keep it. For my friend, there is only one store policy. Even on sale, there are no exchanges or returns.

My husband passed away suddenly and without warning early in our marriage, we were just barely to the first seven-year itch in our relationship. Our friends were still enjoying the initial years of coupling while I was newly single, an occurrence that would change my life forever. It took time to wade through the grieving process, but ultimately I gave myself permission to have fun, to entertain relationships with men of all ages, and to enjoy being single in my second act.

I’ve enjoyed the security and comfort of being one half of a married couple, but that was then and this is now. I wasn’t immediately interested in being coupled again. Given my circumstance of losing my spouse in the tragic way that I did, I initially felt panicked by the thought of it. While my marriage did not endure the end of a honeymoon phase, I was older and questionably wiser and able to reflect inward. Why did I get bored with the same old, sameness? Did I once again want to be limited by one partner for the next umpteen years? Should I just quiet my damn mind and see where this second act takes me?

I decided to remain open to the possibility of a long-term relationship, even marriage one day. In the short-term however, I was curious as to what was out there for me, no-strings attached.

Sure, I could be envious of my friends who celebrated anniversaries with a permanent sofa-mate, dinner-mate, travel-mate, decision maker-mate, but I consciously choose not to go there. While some of these friends are truly happy in their relationships, there are many that are not.

I am in a position to embrace and relish the opportunity my coupled friends do not have. I could date one, or I could date many. Who I date, when, how, why and how old are in my control.

I am also not the same person I was when I met my husband years ago. I am no longer a girl, but a woman who is well respected in her career, and has clarity for her emotional and physical needs. I am comfortable in my body and my skill set. Sex is better – from the pace, to paying attention, to knowing what arouses me and asking for it. I like to be adventurous and I’m not ashamed to show it and share it. I am willing to learn new tricks and enjoy teaching someone a new trick or two. I can carry on a conversation with greater subject knowledge and wisdom. I don’t play games. If I want to say it, text it or sext it, there is no holding back. The thought of “OMG, I have to date!” isn’t daunting or scary; instead, it is an exhilarating windfall. I wouldn’t change a thing about my marriage; I was blessed with a best friend as my partner. However….

Since the day I gave myself the green light to date, I have met some of the most amazing (and not so amazing) men. I have dated men my age, I have dated men older than me, and I have dated men twenty years my junior. I have dated casually and seriously, pilots, professional athletes, businessmen, billionaires, bartenders, scientists and everything in-between. Some of the relationships have been for fun, noncommittal, sex-only romps, while others were more for “adulting” reasons. I can honestly say, that the thought of being with a guy who is 55+ just doesn’t appeal to me. Although I’ve turned down two 26 year-olds, there is one 28-year-old who is still in my contacts. I definitely don’t go hunting for youth, but somehow, they think I am their next prom date. In turn, I confess I know how to flirt when they come knocking on my dressing room door.

I feel extremely fortunate that I have the chance to go shopping for a new prom dress at the store of my choice, where returns and exchanges are accepted, with or without a receipt, even after taking it out for a spin on the dance floor. I’m excited to share my fun and frenzied single dating stories, bringing all those life experiences together, and living in my second act.

Stay tuned!






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  1. Great article! Janey has a great perspective on life and love! I look forward to the next article!

  2. OMG I can totally relate. When you know you want to find the one guy instead of playing with all the players you will find that one guy who is non-returnable and is the man or rather your favorite pair of boots you never want to take off. Love your articles.

  3. This is a refreshing article and so on point!!!! I feel as if I am sitting across the table from you chatting away over a cup of coffee. I am captivated with your words and staying tuned, of course!!!!!

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