Where is this going?


Went on a few dates with a woman far too young to tie herself to a crusty old drunk like me. I was in denial. Finally, she sat me down and asked a set of questions designed to see if I fit into her life plan.

I don’t. I know that. I do admire the kind of woman who knows what she wants and is upfront about it.

I discussed the whole scene with a coworker and three women (right around my age) barside. They all agreed. I should be honest and stop wasting her time.

Her first question was, “Do you think you’re too old for me?”

  • My Answer: “Probably. But, I’m well-trained and you’re not too young for me.”
  • Proper Answer: “Oh, hell yes. What are we doing here?”

The next question is around raising a family. She has young children and wants more. I have no children and want fewer. “I’d like to have more children. How do you feel about that?”

  • My Answer: “Well, you’re perfectly capable. My tubes are disconnected, but we probably could figure something out.”
  • Proper Answer: “I don’t have the patience to raise a house plant. How do you think I feel about kids?”

People often ask across the bar if I’m married. I usually say, “I did my time.” Yep, I’m trying to be silly. My marriage was actually not awful. I’ll always love the woman who married me. I expected and got the next question, “Can you see yourself getting married within a year or so?”

  • My Answer: “I guess if we fall in love, anything is possible.”
  • Proper Answer: “No. Never. Sorry.”

At this point, I’m coming up with answers to extend the date to the part where we wind up naked and deal with the carnage of my dishonest answers another day. I’m not proud. Men are horrible. One more question was lobbed my way. “Would you be willing to move into a larger home in wine country next year?”

  • My Answer: “Ooh, I do love wine country. That would be amazing. I guess it all depends on how things go emotionally and financially over the next year.”
  • Proper Answer: “I just moved here last year. Next to the death of my parents, it was the most stressful day of my life. No. I’m not fucking moving.”

She deserved better. If I gave the proper answer in any of those cases, that would have been it. Yet, although I was trying to mold my answers, she could see through it all. The night ended with a peck on the cheek and three fingers of fine Cognac while my cat (Syd) sat next to me cleaning himself. We shrugged.

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About the author

Author of humorous essays about relationships and lifestyles.