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The Tryst

Posted on February 12, 2020November 3, 2026 by Dating Goddess

He is smart, funny, charming, good looking, worldly, educated, successful, a sharp dresser, good listener and conversationalist. He tells you what you long to hear. He is vulnerable with you and you with him. His kisses and caresses make you feel what you haven’t felt in a long, long time. He tells you how sexy and adorable you are, and how much he misses being with you.

You met through business, not online, so you know he’s not a player.

Yet there are things about him that on paper would be deal breakers.

  • There are decades of age difference.
  • He’s not fully divorced and the uncoupling is complicated.
  • He lives an hour away.
  • He has a lot on his plate with family issues so isn’t fully emotionally available.
  • He’s got a demanding job so doesn’t have a lot of time available to see you.

Your logical mind tells you to say no to his overtures, which you did for a month, as you kept his frequent texts in the friend zone. But he started to share his feelings about you, and you found yourself becoming emotionally entranced.

After seeing each other a handful of times, you found yourself not only succumbing to his charms, but welcoming them. You knew all the reasons this would never work long-term, but you couldn’t help yourself. You loved how he seduced you.

Afterwards, you remind yourself of the reasons you should not be smitten, but the heart overrides the head. He tells you he greatly cares about you, you are on his mind a lot, he shouldn’t have let his feelings take over as he knows it now complicates things.

You agree that both of you took things farther than you should have. But what’s done is done. Now what?

If you value what he adds to your life, you go back to being pals. A tryst is just a tryst. No need to get hung up over it. Enjoy the memories of what was. It’s not worth ending a good relationship over a slip in judgment.

Category: Dating after 40

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About the Dating Goddess

After her 20-year marriage dissolved, the Dating Goddess dated 91 men in 3.5 years. She shares her lessons, stories and advice for midlife women reentering the dating scene.

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