Strawberry Letter

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Latest Episodes:

I'm Falling In Love With A Big Baby Jun 08, 2020

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Dear Steve and Shirley, I’m 40 years old and my boyfriend is a 45 year old, successful businessman. He’s divorced and has one kid from his marriage. We’ve been dating for 7 months and I love his kid and I get along well with his ex-wife. A few weeks ago, his ex and I were chatting in the driveway when she dropped their child off. She asked me if my boyfriend had revealed his big secret to me yet. I asked her what she was talking about and she assured me that it wasn’t about him cheating or anything like that, but it’s very strange and it was the cause of their divorce.

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I Found Out That I Married A Drunk Jun 05, 2020

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Dear Steve and Shirley, my husband and I got married in January and I relocated to be with him, after the wedding. We dated for 2 years in a long-distance relationship before we got married. When I moved in with him, I found out he has a split personality. To my surprise, he used cocaine recreationally and he’s a binge drinker. I never saw this side of him when we were dating. The truth came out on our wedding day. He started drinking mid-day and looked like he was high..................

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My Man Treats Me Like An Afterthought Jun 04, 2020

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Dear Steve and Shirley, I’ve been in a relationship for almost two years and when I think about the things this man has shown me sexually and mentally, I am floored. He literally takes my breath away. But there are a few problems with our relationship. We’ve never spent a night together and I’ve never met his family, except for his twin daughters and their mother. It was a quick “Hi” and “Bye” when we ran into them at Target..............

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I've Fallen In Love With Her Boyfriend Jun 03, 2020

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Dear Steve and Shirley, I’m a single female and I moved to a new city 3 years ago, for a new job. I did not have any family or friends in the city, but I instantly bonded with a male co-worker and we’ve become really close. He was really great at helping me get settled and showing me around town. He has a girlfriend of 8 years and a child and I’ve always respected that. We would get flirty here and there but it was always harmless, at first...............

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I Am The Only One That Can Have Sex In My House Jun 02, 2020

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Dear Steve and Shirley, I am a 37 year old divorced man and I'm in a one hell of a situation. I have a 5 year old son that has a lot of health issues, so my ex-wife and I decided it was best if we were all on lockdown together. I have custody of my son but she helps me out a lot with his medical care, so she moved back in with us temporarily. Everything was cool at first, but by mid-April, my ex was up to her old tricks.............

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The Two Women That I Love Most Jun 01, 2020

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Dear Steve and Shirley, I’m a 37 year old man and I’m in love with the perfect woman and I want to marry her. I am financially secure and I love taking care of my family. I bought a new home 5 years ago and I made sure I had a separate space for my mother to live comfortably. She has her own entrance from the garage, so she’s still independent. She does most of the cooking and I am happy to have her with me...............

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My Boyfriend And I Sleep In His Ex's Driveway May 29, 2020

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Dear Steve and Shirley, I am a 29 year old female in a confusing dating situation. We’ve been dating for almost 2 years but I waited for 4 months before we had sex, to make sure his last relationship was totally over. He has 3 kids by three different women, but the youngest child’s mother has been a problem in our relationship. My boyfriend lived with her when we met, but now he lives inside his RV, that’s parked in her driveway..................

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I Can't Even Get Drunk In Peace May 28, 2020

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Dear Steve and Shirley, I'm a 45 year old black man. My fiancé is 56 and she’s a great woman, but I’m worried about marriage. We like to kick back and relax and drink wine and alcohol. It depends on our mood, so sometimes it’s wine and sometimes it’s the hard stuff. We pretty much drink every day after work. I’m more relaxed and mellow when I’ve had a few drinks, but she is the opposite of me. She likes to get angry, cuss and fuss and bring up a bunch of old stuff, trying to start an argument.................

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Two Is Company, But Is Three Always A Crowd May 27, 2020

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Dear Steve and Shirley, I have been in a relationship for 5 years with a man that thinks we are exclusive. I’m in my late forties and my sex drive has been through the roof lately. My boyfriend is 53 and he’s a beast in the bedroom, but he’s not enough for me and he’s not as kinky as he should be. For the first time in my life, I am a cheater. I’ve been having sex with a 30 year old neighbor and it is fun and spontaneous and he gives me the fire that I desire. This is not the only man I’m seeing on the side though...............

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Noisy, Naughty New Neighbor May 26, 2020

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Dear Steve and Shirley, I’m a 38-year-old married woman and my husband and I have lived downtown in a nice condo for the past six years. We get along well with all of our neighbors but a couple months ago, a single young man moved into the condo next door to us and now we’re having a big issue with him. Since we’ve all been quarantined, our neighbor has been into porn and it’s driving my husband and I crazy..............

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