Dear Gail: Coffee Is Not a Red Carpet Event

Can a t-shirt and jeans be insulting? Can a dog play cupid? Comedian Gail Forrest answers your dating questions.

Coffee Is Not a Red Carpet Event

Dear Gail:
Generally my first dates are for coffee or lunch. I always tell the woman to feel comfortable and dress casual. I’ve had several women arrive in faded jeans, sandals, or t-shirts. Yes, they may feel comfortable, but what does that say about what they think about me or dating that they can’t bother to dress appropriately?

Dear Bryan:
Well for sure I could never go on a date with you as I still wear my COVID sweat pants out for coffee. It seems you have a very specific definition of the word “appropriate.”  My question to you is, how would anyone know what it is?  And you did say the word “casual” which could easily mean jeans, sandals and t-shirt, unless it’s high tea at Windsor Castle. 

I have had men arrive in embarrassingly tight gym shorts, baggy old sweat pants, and clothes entirely covered in Blackhawk logos (that was award winning but horrifying). I passed judgement on them for having really bad taste and no mirrors, but did not take it personally.

I say coffee is a fashion throw away. Start with a first date for dinner at the Peninsula and get back to me.

Dogs Are Definite Date Bait

Dear Gail:
What do you think of dog parks as a way of meeting men? I’ve heard guys say dog parks are “chick magnets” but is the reverse true? Are dog parks “guy magnets”?  Do you have any luck with this?”
Joyce R

Dear Joyce:
BINGO! I had so much luck out with my Golden Retriever Jonah I found a husband attached to a Golden Retriever named Lancaster. We had matching dogs, politics, and were from the same suburb of Chicago while meeting in the middle of Central Park. It was the dog trifecta. And still makes a good story regardless of the divorce.

Dogs are man bait trust me, darlin’.  Everyone out walking a dog wants to talk especially about their pooch. Just start with “what a cute dog.” Don’t stop there!  Say something else, anything else, just keep chatting. A sports reference is definitely man bait and usually fool proof. Ex: “How about that Bear game Sunday? They sucked.”

Make a big fuss over his dog which hopefully isn’t mauling or humping yours.  

Good luck arffffffff

Need advice? Gail wants to hear from you. Send your letters, questions, and quandaries to: newsletter@weareageist.com


  1. In America we spell judgment without the e after the g, idk why, but that’s the way it is. Think Terminator 2: Judgment Day.

    • Wow thanks for the correction as I appreciate spelling/ grammar advice. Wonder why auto-correct didn’t pick it up. And btw never saw the movie so of couse I didn’t know. Yes, we New Trier grads are part of the grammar police….I know I am. Thanks for reading!

  2. Heh, funny. Being a cat corraler myself, Ive never been in a dog park. The term “cat park” … makes no sense. There’s a cat tourist island in Japan, population 100% cats, but that’s a long way to go for a date.

    I suppose I could rent a dog, right?

    Btw, Winkless also made an attempt to correct me on my use of the word “akimbo”. Although I was correct in my usage, I appreciate his effort. 😎

    • OMG can you imagine a cat park? No one would ever go home with the same cat! Or find their cat again. That is a craaaaazy notion, but fun to imagine. People running helter skelter to corrale the independent feline who would be happy with anyone who fed them.
      At least Terry is keeping a keen eye on us!

  3. There may not be cat parks, but there are cat cafes. You can get a latte with cat fur on the steamed milk, a head butt and potentially a new cat. Not certain it’s guy magnet.

    • Probably not a good guy pick up place. I will say one thing about owning a cat , which I have done, if they miss the litter box you have to move for the ever lingering odor. I do know men who love cats however so it could replicate a dog park


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Gail Forresthttp://www.gailforrest.com
Gail Forrest is a comedy writer and stand up comic. She studied at Second City in Chicago and has performed at Pretty Funny Women and Flappers in LA, as well as Second City to name a few. She has a published book Gonepausal on Amazon about women in midlife and is working on a new book which includes men and promises to be just as funny with even more insights on aging.


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