by Meredith Siegel Cohen, Creator, Single and Striking Out
A few months ago, I was on a date with a man who was fourteen years my senior. It was the biggest age gap I’d ever entertained, but he was so warm, engaging, and accomplished that I couldn’t pass up the opportunity to meet him.
Right out of the gate our dinner began with robust conversation. He was as curious about me as he was eager to share about himself. We talked about our career paths, children, travel experiences, hobbies, and wishes for the future. After some time, he asked about my relationship background.
I enjoy having these conversations up front, because if we’re being honest, it’s what we all want to know. What happened in your marriage? Why did it end in divorce? Tell me about your relationships since then.
You can get a sense of honesty and sincerity pretty quickly. Does the person hold space for personal accountability, or does their “version” (because we all have one) paint them as the victim? Body language is a dead giveaway, as you can often see it at once: a sudden avoidance of eye contact, discomfort shifting in their seat, fidgeting. It’s a fascinating study of human behavior.
So there we were, chatting and sipping our cocktails, going full throttle on the dialogue. He asked about my last long-term relationship, and I gave him some background. Then he asked:
“Do you think you made a mistake breaking up with him?”
SCREECH! BRAKES SLAMMED.
Not one for a lack of words, this question stopped me in my tracks. The room felt suddenly silent as I stared at this stranger across the table. Speech didn’t come right away. I couldn’t find my words.
Why would he ask me that? I had never been asked that question before. Was I talking too much about my ex? Could he sense that I still harbored feelings? Wasn’t that a little too personal for someone I had just met?
And why was I taking it so personally? Why was my face flushing, my back growing hot? It felt as if someone had called me out on a lie—or uncovered some deep, dark secret I was hiding.
But he wasn’t calling me out. He was simply asking an innocent question.
I stammered. I couldn’t directly answer him.
I don’t recall exactly how I handled it, but I know I said something like, “No.”
That date was a one-and-done—not because of the question, but because the age gap ultimately felt too wide for me. Still, I usually believe there’s a reason someone crosses our path. Everyone comes along to teach us something.
In his case, I needed to grapple with that question.
Did I make a mistake? Should I have stayed in the seven-year relationship?
How many times have I written that relationships aren’t perfect? Sometimes it felt loving. Sometimes it felt committed. Sometimes it felt like enough. Maybe it was enough. Maybe I had given up the last real relationship I would ever know.
Sigh.
I sat with the question. I journaled. I thought about it for a while.
And then the answer hit me like a ton of bricks. I wasn’t uncomfortable because I believed I had made a mistake leaving. I was uncomfortable because I felt shame for staying as long as I did when we both knew it wasn’t right.
The truth—the answer I should have given—was this:
My mistake was not leaving sooner.
I did love him. I’m not sure the feelings were fully reciprocated, but I loved him. And I tried.
I communicated my needs—over and over again. I tried to accommodate his. In the end, we simply couldn’t give each other what we needed or wanted.
Here’s the hard part: we both knew, about three months in, that there were major roadblocks. But out of a desire to be together, we chose to ignore them. I promised myself that if things hadn’t changed in a year, I’d end it.
Good luck with that once feelings take root and comfort sets in. Try just “walking away” then. It’s not so easy.
I would break up. He would reach out. The cycle would begin again. I wasn’t strong enough to hold firm.
If I had been an outside observer—if this had been a close friend’s relationship—I would have had some pointed words to say. You are young. You are beautiful. There are so many opportunities out there. Date others. Try. Why stay in something that isn’t bringing you happiness? Why stay in something that makes you cry, that makes you feel like a second rather than a priority?
The purpose of this piece isn’t to condemn or criticize him. We both carry responsibility for that relationship.
The purpose is to reach someone sooner.
If you’re reading this and nodding your head—wondering why you’re clinging to something that isn’t truly working—ask yourself if you’re making a mistake. Time is our most precious commodity. I gave seven years to a relationship that should have ended in three months.
Because it’s about the now. The present. We shouldn’t endure in hopes of reaching some future, perfected version of a relationship. The basics should be there from the beginning. And you’ll know quickly—because your gut will speak up when your head wants to weave a different narrative. The real challenge is heeding your intuition and standing firm when the truth isn’t what you want to hear.
What a lesson to learn. And what a lesson to pass on.
If I can impact even one reader, that matters.
As I date now, I carry that experience with me. I think about my needs, my worth, and my right to want what I want. I assert boundaries. I trust that this will move me more quickly toward people with true match potential.
I wish him well. I wish all my dates well. They are mostly good people—like me—just trying to find love and happiness in the short time we have on this earth.
Lessons are interesting, if we’re willing to open our eyes to them. It took me seven years to find the strength to open mine.
Let that be a lesson to you.
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