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Most Hilarious “Dear Abby” Enquiries


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  • Andr-Tech

Most Hilarious “Dear Abby” Enquiries

Remembering the original 'Dear Abby' Pauline Phillips, whose "Dear Abby" visited the homes (via the newspaper and online) starting in 1956. 

Pauline-Phillips.png

She took on the pen name Abigail Van Buren and began giving sometimes controversial, sometimes helpful, and oftentimes hilarious relationship advice for both men and women.

Phillips died on 16 January 2013, at age 94, after battling Alzheimer's for 11 years.

Even Dear Abby Was at A Loss to Answer the Following:

  1. Dear Abby, for years I have heard about players winning thousands of dollars on casino slot machines. But every time I try to win one, I run out of cash before hitting it. How can I win a jackpot before I go broke? Hurry your answer because my money is running out. 
  2. Dear Abby, why does our society insist on using the euphemism "sleeping together" in place of "having sex"?
  3. Dear Abby, I am a 23-year-old female who lives with my parents. I saw "The Little Mermaid" for the first time recently, and now I'm very worried. The other day I walked in and caught my mom talking to my pet fish. Mom breaks into Broadway-style songs randomly, just like Ariel did in the movie. She also has the same red hair as Ariel. Could my mom be half-Mermaid? Am I half-Fish? I will await your reply before attempting underwater breathing. Please answer promptly.
  4. Dear Abby, at what time does "today" turn into "tonight"?
  5. Dear Abby, a couple of women moved in across the hall from me. One is a middle-aged gym teacher and the other is a social worker in her mid-twenties. These two women go everywhere together and I've never seen a man go into or leave their apartment. Do you think they could be Lebanese? 
  6. Dear Abby, what can I do about all the Sex, Nudity, Fowl Language, and violence on my phone?
  7. Dear Abby, I have a man I can't trust. He cheats so much, I'm not even sure the baby I'm carrying is his.
  8. Dear Abby, I am a twenty-three-year-old liberated woman who has been on the pill for two years. It's getting expensive and I think my boyfriend should share half the cost, but I don't know him well enough to discuss money with him.
  9. Dear Abby, I’ve suspected that my husband has been fooling around, and when confronted with the evidence, he denied everything and said it would never happen again.
  10. Dear Abby, our son writes that he is taking Judo. Why would a boy who was raised in a good Christian home turn against his own?
  11. Dear Abby, I joined the Navy to see the world. I've seen it. Now how do I get out?
  12. Dear Abby, my forty-year-old son has been paying a psychiatrist £200.00 an hour every week for two and a half years. He must be crazy.
  13. Dear Abby, I was married to Bill for three months and I didn't know he drank until one night he came home sober.
  14. Dear Abby, my mother is mean and short-tempered. I think she is going through mental pause.
  15. Dear Abby, you told some woman whose husband had lost all interest in sex to send him to a doctor. Well, my husband lost all interest in sex and he is a doctor. Now, what do I do?
  16. Dear Abby, I was awakened at 3 a.m. by a barking police dog while someone was being arrested on my front lawn. This morning, I discovered the dog had pooped on my grass. I'm considering complaining to the police about it, but don't want to seem ungrateful for the job they do. What do you think? 
  17. Dear Abby, I know boys will be boys, but my ‘boy’ is seventy-three and he’s still chasing women. Any suggestions?
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