Dear Gail Archives

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

Dear Gail 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...

Dear Gail: Can You Have Too Much Sex?

Dear Gail 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...

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

Dear Gail 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...

Dear Gail: You Have to Pay to Play

Dear Gail 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,...

Dear Gail: Wait, Wait, Don’t Tell Me

Dear Gail 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...

Dear Gail: Sleep Divorces Are on the Rise

Dear Gail 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...

Dear Gail: Here Comes the Bride Again!

Dear Gail 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...

Dear Gail: Where Oh Where Did My Hair Go?

Dear Gail 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,...

Dear Gail: Dating Sites — Everybody Lies

Dear Gail 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...

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