Strawberry Letter

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Latest Episodes:

He Keeps Sneaking Women In My House Nov 20, 2020

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Dear Steve and Shirley, I'm a 44 year old mother and I allowed my 24 year old son to move back home after college. I had hoped that he would find a great job and get his own place, but he wasn’t so lucky, so I told him he could come home temporarily. My house rules are the same as when he was in high school. He’s expected to keep the house clean and the lawn looking good, in exchange for housing. Our bedrooms are on opposite sides of my condo so I rarely see him because of our work schedules and his social life...............

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I Need It So Bad I'll Wear A Mask Nov 19, 2020

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Dear Steve and Shirley, I am a 58 year old widow and I’ve been dating my current man for the past 10 years. He refers to me as his wife and most people think we are married. Truth is, I haven’t married him because I still get my deceased husband’s pension and he is okay with that. Before Covid-19, we were inseparable. We don’t live together, but he was with me day and night.....................

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I Have Three Boyfriends But Somethings Missing Nov 18, 2020

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Dear Steve and Shirley, I’m a 29 year old woman with a great job and a great body, pretty face, and 3 boyfriends. One boyfriend is 38 and he’s an oil company executive. One is a 39 year old police detective. The third one is only 21 and he’s a manager at a retail store. They are all good financial providers and the youngest one is muscular and very handsome. The two older ones spoil me and I travel extensively with one of them.................

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She Said I’m Obsessed with Sex and Money Nov 17, 2020

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Dear Steve and Shirley, I’ve been living with my current girlfriend for 2 years and everything is great until we start talking about our finances. I’ve worked since I was a kid and now all I want to do is save money and keep my small black-owned business afloat. My girlfriend is not good with money and she’s lived check-to-check since I’ve known her. I’ve talked to her about saving money and getting her credit straight so creditors will stop calling her...................

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The Cat Is Out Of The Bag Nov 16, 2020

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Dear Steve and Shirley, I am a 55 year old, married, successful woman, sleeping with my son’s best friend. He and my son have been the best of friends since the second grade and now they’re both 27 years old. The best friend, who we’ll call David, has been working with me for a year, as my accountant. I let the rest of my employees work from home during Covid-19, but David came into the office to complete our annual taxes and that’s when it started................

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I Couldn't Give Her A Baby, But He Did Nov 13, 2020

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Dear Steve and Shirley, I am a 53-year-old man and my fiancé is 35. We’ve been together for 4 years and from the beginning, she told me she wanted to be a mother. I was married before and I’ve got 3 children… and I’ve had a vasectomy. As our relationship got serious, I told her I could get my vasectomy reversed and I would give her a baby. I visited my doctor and I was told that I had a bit of scar tissue from the surgery, so it could not be reversed.................

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Your Best Friend Is My Girlfriend Nov 12, 2020

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Dear Steve and Shirley, I was married for 4 years and at first, my marriage was great and my wife was sexy, classy and ratchet so we had a lot of fun together. She was a very sexual woman so she talked me in to going to a swingers group. My wife liked it so much that she started having an affair with one of the guys she’d had sex with at the swingers party. I found out and I was so hurt. She begged me to forgive her and I did, but things did not go back to normal in our marriage...............

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We Live In A Shack, But We're Not Shacking Up Nov 11, 2020

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I Have To Watch My Back Now Nov 10, 2020

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Dear Steve and Shirley, I’m a 30 year old black man and I grew up in a middle class family, but I had a lot of friends. A lot of my friends were from a different background because I’d meet them playing sports or hanging out. I went to college and came back home and realized I’d outgrown a lot of my friends because they were still living at home with their parents and didn’t have a real plan for their lives................

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I Told Him Not To Go To Her Funeral Nov 09, 2020

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Dear Steve and Shirley, I have been married for 25 years to my soulmate and we had a great life, until 3 years ago when I caught him cheating. One night when he was supposedly hanging out with his boys, he called me and said he was too drunk to drive home. I offered to go get him, but he said he was going to sleep it off and come home soon. I called to check on him at 6am and a woman answered his phone...............

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