Strawberry Letter

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Latest Episodes:

My Best Friend’s Wife Too Much Jun 21, 2021

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Dear Steve and Shirley, I am a 27 year old man and I have a best friend and we've been super tight for years. We have been thru all the good and bad girlfriends together and now that he’s married, I want to tell him so bad that his wife is too much. She’s too much of everything. She’s tall, thick, wears big hair, big lashes and her nails and toe nails are very long.....................

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Three Years Later and We’re Only Friends Jun 18, 2021

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Dear Steve and Shirley, I’m 34 years old and my significant other is 39 and we’ve been together for 3 years. I call him my significant other because he has yet to define our relationship. We started as friends, just like most couples do and as we got closer, he told me that he didn’t want anything serious but he enjoyed spending time with me. We started having sex a month after we met and at that time, I was very busy at work and helping my sister with her new baby, so I was not ready for anything serious either.............................

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My Mama Needs Some Clothes Jun 17, 2021

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Dear Steve and Shirley, I'm a 26 year old married woman and I’ve let my mother stay with me for 3 months. We live four hours apart so when I had my first child, she came to help out. My mom is one of those older women that looks great, dresses in trendy clothing and loves to change up her hairstyle. She’s single now after going through her second divorce and she lives with my grandparents...............

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My Homie Is My Sidepiece Jun 16, 2021

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Dear Steve and Shirley, I'm a 32 year old single man and I started a sexual relationship with a female that hangs out with me and my boys. She’s like one of the boys and we party together, work out together and she travels with us on our annual guys’ trip. She is a good friend and we respect her and her sexual preference. We’ve never talked about her love life, but I assumed she never dated a man before. We’ve been friends since middle school and she has always been a pretty girl........................

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What More Does He Want From Me Jun 15, 2021

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Dear Steve and Shirley, I’ve been with my fiancé for 3 years and we’ve been engaged for almost a year. We have had sex almost every night since we met. Since he proposed, he’s been wearing me out physically. He has raised the bar so high in the bedroom that I can’t keep up. He’s doing all kinds of positions and tricks on me nightly and I’m exhausted. He knows I work two jobs and we have a small child to take care of...................

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He Who Finds A Wife Jun 14, 2021

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Dear Steve and Shirley, I am in need of advice. I am a 36 year old divorced man and I’m engaged to be married. I’m a middle school teacher and I have 2 children by my first marriage. My first wife is also a teacher at the same school and we divorced after I caught her cheating on me in her car with the track coach at our school. After the scandal, he transferred to a high school and my ex-wife married him. It was hell to have to work with her after she moved on with the guy that she cheated on me with..................

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Watch How You Talk To My Baby Jun 11, 2021

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Dear Steve and Shirley, my boyfriend and I have been together 2 years and we had planned to get married soon but I got pregnant instead. He’s 27 and I’m 25 years old and we moved in together so he could help me with the baby. My family didn’t really care for him before I got pregnant and they really don’t like him now since he's still not working and I’m paying all of the bills. Let me set the scene for you...................

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Casanova Is Living In My House Jun 10, 2021

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Dear Steve and Shirley, I am a 55 year old mother, still raising a 24 year old man and he’s still living in my house. All of my family calls him Casanova because he’s very handsome with a head full of black curls. He’s never been full of himself, but he’s well aware of how good he looks. He’s never been in a relationship and when he was in high school, girls used to call my house so much I had to restrict calls sometimes..................

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My Daddy Loves My Friends Jun 09, 2021

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Dear Steve and Shirley, I am a 30 year old single woman, forced to live with my 46 year old father for the first time ever in my life. I moved in with him last year after I got pregnant and lost my job all in the same month, during the pandemic. My parents got pregnant with me in high school, so I was raised by my 2 grandmothers and I thought of my dad as an older brother or a playmate because he didn’t do anything but play with me when I was younger...................

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Is This Considered Cheating Jun 08, 2021

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Dear Steve and Shirley, I have been in a relationship for 4 years and my boyfriend and I live 3 hours apart. We’ve always been in a long-distance relationship and I thought everything was fine, until recently. He started talking about marriage after we dated 2 years and he said he would gladly move to Philly to be with me. I got all excited about marriage and I started preparing myself emotionally and financially to be with him for the rest of my life....................................

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