Gail Forrest

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http://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.

Dear Gail

Dear Gail: There’s No Place Like Home… on a Vacation

Gail Forrest - September 13, 2023

There’s No Place Like Home… on a Vacation Dear Gail: My GF and I are going on a vacation together for the first time as a couple. We’re in our mid-sixties. Both of us are thinking that this vacation could really be important for our relationship to see how we get...

Dear Gail

Dear Gail: Can You Have Too Much Sex?

Gail Forrest - September 6, 2023

Can You Have Too Much Sex? Dear Gail: I am a 72-year-old man who's been dating a 68-year-old smart, successful, attractive, SEXUALLY INSATIABLE woman for the past 1 1/2 years. I’m sure there are multitudes of men that envy me but “be careful what you wish for.” I’m tired. I can’t...

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Dear Gail: Your Best Friend’s Husband on Tinder… Shhh or Rat Him Out?

Gail Forrest - August 30, 2023

Your Best Friend’s Husband on Tinder… Shhh or Rat Him Out? Dear Gail: I was scrolling through Tinder the other day and saw my best friend’s husband on it. There is no doubt that it was him. I have not heard her mention any problems with their marriage so I was...

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Dear Gail: You Have to Pay to Play

Gail Forrest - August 19, 2023

You Have to Pay to Play Dear Gail, I have been with my partner for eight years and we are both in our seventies. We, however, have different views on two important issues. 1) I believe that if you put your partner first and they do the same, you'll have a...

Dear Gail

Dear Gail: Wait, Wait, Don’t Tell Me

Gail Forrest - August 11, 2023

Wait, Wait, Don’t Tell Me Dear Gail, All my adult life people have made comments about my stuff: clothing, hair, even my car. Just the other day, a colleague (with whom I'm on good terms) said, “Your hair looks good today, now that it's grown out.” Another person commented on a dark...

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Dear Gail: Sleep Divorces Are on the Rise

Gail Forrest - August 9, 2023

Sleep Divorces Are on the Rise Dear Gail: My girlfriend and I recently started to co-habitate. When we used to weekend together I thought her little snore was cute. Now night after night it’s making me crazy, even seems to have grown louder. I’m sleepless and exhausted. I’ve casually mentioned it...

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Dear Gail: Here Comes the Bride Again!

Gail Forrest - August 2, 2023

Here Comes the Bride Again! Dear Gail, I’m a 55-year-old divorced woman in Chicago with a 60-year-old fiancé. He is obsessed with the idea that we be married and honeymoon in Las Vegas: the home of casinos, gambling, mobsters, blinding neon lights, show girls, and overall tackiness. But then should I care...

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Dear Gail: Where Oh Where Did My Hair Go?

Gail Forrest - July 27, 2023

Where Oh Where Did My Hair Go? Dear Gail, I’m a 55-year-old man and losing my hair. I used to have thick brown hair and now, on top, barely a hair. I don’t recognize myself. Should I: shave my head, get a toupee, spring for a costly, painful hair transplant, or...

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Dear Gail: Dating Sites — Everybody Lies

Gail Forrest - July 17, 2023

Beware of the Big Dating Mistake Dear Gail: I have committed the ultimate dating site faux pas. I sent a message to the wrong recipient. Knowing full well there is no redemption, I nevertheless turn to you, the dating Guru, for help. Here are some of my ideas. A) change my...

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Dear Gail: Willing to Risk Your Life for Love?

Gail Forrest - July 11, 2023

Willing to Risk Your Life for Love? Dear Gail, I’m 45 and have been dating a guy who is 55. He’s a gentleman, honest, romantic, and money is no object. Here’s my problem — he’s a born adventurer/explorer type and I’m not. Surfing on high-risk coastlines, wingsuit gliding, mountain climbing (did Everest)...

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