The Most Embarrassing Date

Story submitted by: jeffadmin


When my older sister Judy was in college, a nice young man named Leonard invited her on a date to a dinner theater. Judy was smitten with Leonard and spent a long time searching her closet for the perfect outfit to wear on Saturday evening. She finally decided on a red dress and held it up for my approval. “Do you think Leonard will like it if I wear this?” she asked.

“Of course, Judy,” I assured my sister. “You’ll look very pretty that night.”
On Friday evening, our family was just sitting down to dinner when the doorbell rang. “I can’t imagine who that would be,” our father said as he got up from the table to find out. A minute later, he asked Judy to come to the door. Leonard was standing on the front porch in his new suit and tie, ready to take my sister to the dinner theater. But he had gotten the date wrong and shown up on Friday evening instead of Saturday.
Poor Judy was so surprised that she didn’t know what to say. Fortunately our quick thinking mother invited Leonard inside, apologized for the mix-up, then asked him to join our family for dinner. Leonard looked extremely embarrassed, but he sat down with us at the table and tried to make the best of a very awkward situation.
The following evening, Leonard returned to our home to take Judy to the dinner theater. When he said hello to our parents, he joked about his surprise visit the night before. I could even hear Judy and Leonard laughing about it as they walked out to his car. I can’t remember how the date turned out, but I do recall that my sister was happy to be dating a man with a good sense of humor.

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