Why I Should Have Listened to Everyone About Not Dating a Much Older Man

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If you’re dating a man who’s older than you, especially if he’s more than 20 years older, you can pretty much plan on people talking behind your back. He can look like Brad Pitt, but they still know he’s a generation older, and they’ll still wonder what you are doing with your life. The worst part is that you will probably not have any idea what is being said behind the scenes, until a well-intentioned friend or acquaintance fills you in.

I learned what one of my friends was thinking—through another friend—and her comments were, “Why is she wasting her youth? She’s so pretty; she could find someone her own age and get married.” My much older man, Sam, didn’t want to get married. He had already been married for 25 years, had four children, and didn’t want to do it all over again. Exactly what was I thinking with regards to what I wanted for my own life?

At 24 years old, still with so much life ahead of me, I just figured that I knew what I was doing, and that our age difference would not be an issue. I had convinced myself I wasn’t interested in having children, which coincided quite well with the fact that Sam had had a vasectomy after his fourth child was born.

When Sam and I finally broke up, 10 years after our relationship first started, I was 34 years old. I had to come to grips with why I had let so much time go by with a man whom I knew would never marry me. After we broke up, I was also beginning to change my tune about being childless for the rest of my life. But my chances of meeting someone, getting married, and having kids while I was still young enough were now considerably narrowed.

When my relationship with Sam ended, all of those well-meaning friends came out of the woodwork. While they all genuinely did like Sam—as all of them told me—they also felt like I was giving him too much of my precious youth, and that the partnership was not an equal one in this respect. Sam knew he was done with marriage and children, while I had barely begun, despite getting married too young at 19 and divorcing five years later.

I had been asked out more than once by co-workers, even though they knew I was with Sam. They’d just say they couldn’t believe I was truly “serious about that old guy,” and that I should date them instead. While these guys weren’t my friends, they were still indirectly giving me their outlook on my life too.

In retrospect, I wish some of my friends had conveyed their views when I probably needed it the most. Happily, I did end up getting married again, but even though we tried, I was never able to conceive. Whether I would have ever been able to, of course, is something I’ll never know.

What I do know is that things would have turned out much differently had I not devoted 10 prime years to someone 22 years older, and who had “been there and done that” before I had. I wish I had been kinder to myself, and thought more of my own needs.

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Emilee A

About Emilee A

Sam was my new boss. I was 24; he was 46. We were both married, and I was immediately attracted to him. We began having lunches off campus, then crafting ways to meet for drinks after work, dinners out, even the occasional Saturday when I would tell my husband I was spending the day with a girlfriend. During this time, I asked my husband for a divorce. What young husband could compete with a worldly, mature executive who knew how to treat a lady? Sam took me to expensive dinners, on lovely vacations, and he knew what to do in the bedroom. But as the years went on, our age difference began to rear its ugly head. He became increasingly jealous and possessive. I found out from his son that he even kept a journal on me. I spent 10 years with Sam—10 years of being with a man who, because of his age, would not marry me and would not give me children, as he’d “been there, done all that.” Sam always told me he made “a better boyfriend than a husband.” I wish I had listened…

The “Soft” Truth About Sex with an Older Man

What Happens After Dirty Talk with a Wealthy Mature Man (Absolutely Mind-Blowing): Part 1

How I Stopped My Friend From Trying to Steal My Sugar Daddy

The Worst Time in Your May-December Relationship to Bring Up the Topic of Marriage: Part 2

What I Told My Family (and Everyone Else) When I Started Dating an Older Man

The Worst Time in Your May-December Relationship to Bring Up the Topic of Marriage: Part 1