Strawberry Letter

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Latest Episodes:

His Wife’s Picture Is On The Nightstand Aug 03, 2020

Show notes

Dear Steve and Shirley, I am a 53-year-old single female and I’ve been casually dating a man for 3 years. His wife died 6 years ago and he’s a single dad, raising a daughter. He lives in my complex and when we met, we instantly clicked and started dating. After a few months of dating, he told me he wanted to take a break so he could focus on his daughter. That was 3 years ago and I showed support by cooking for him occasionally and showing up at some of his daughter’s basketball games..............

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I Asked A Married Woman To Marry Me Jul 31, 2020

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Dear Steve and Shirley, for the past 10 years, I have lived with a really good female friend. Over the years, we’ve shared a bed at times and we’ve had sex when it was convenient. Other than that, it was more of a roommate type of arrangement. She dated other men and I dated other women. When we were at home, we were best friends that happen to sleep in the same bed sometimes. We never had our boyfriends/girlfriends sleep over..............

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My Frumpy Friend Needs A Makeover Jul 30, 2020

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Dear Steve and Shirley, I’m a 29 year old woman and I need your advice on how to help a friend. She’s been in quarantine alone so all I’ve been hearing is how lonely she is. Well, here’s why… She looks a hot mess all of the time and being inside for 3 months has made it worse. I know everybody has been looking crazy since we are stuck inside, but she’s put on a few pounds and looks like she hasn’t combed her hair since March...................

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You're Single Unless You're Married Jul 29, 2020

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Dear Steve and Shirley, I am 36 years old and I’ve been in a great relationship for 4 years. A year ago, I noticed a change in my man and changes in our sex life. If I initiated sex, he made up excuses like he has acid reflux and he’s scared sex might give him a heart attack. Then I saw a text on his phone that said, “I love you too.” I asked about it and he said he texted her some relationship advice and was only responding to her...................

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I’m Well Known By A Lot Of Men Jul 28, 2020

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Dear Steve and Shirley, I'm a 44 year old woman who's been with a man for 5 years and he has had the same complaint for 5 years. He always whines about me knowing too many men. I was raised in the city we live in and my father was a prominent businessman and my family is well-known. When my boyfriend and I would go out, I'd run into guys that I grew up with, guys I worked with, went to high school or college with, etc. These are men that I’ve never dated or had sex with..................

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Love Can Make You Do Some Crazy Things Jul 27, 2020

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Dear Steve And Shirley, I am a beautiful black 29 year old woman and I’m in love with a deadbeat dude but I don’t know how to get him out of my system. He’s 36 years old and we currently live with his parents. When I met him, I was the side piece for a year. I got pregnant and had nowhere to live, so he let me live in his car. His parents found out about me and they let me stay with them. Now he's divorced and our relationship is complicated. I found him at a bar with a female recently and I poured his beer on him..................

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I Have A Rat In My Basement Jul 24, 2020

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Dear Steve and Shirley, I’m a 48-year-old man and my wife and I have a 23 year old daughter that graduated from college and she moved back home. She asked her mom and I if one of her school mates could live in our basement for three months. I was hesitant, but my wife coerced me to let the young man stay temporarily. He was polite at first but then he started coming upstairs and trying to engage with our family.................

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Why Can't We Both Have A Sidepiece Jul 23, 2020

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Dear Steve and Shirley, my husband and I have been married for 3 years. Our marriage was going good until a year ago, when he told me he was having an affair. Shortly after we met, he told me about a female friend of his that lives out of town and she’s like a little sister to him. I met her 5 years ago when she came to town for homecoming. We got along great, but I don’t trust any females around my man...............

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He Really Thinks I Took Advantage Of Him Jul 22, 2020

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Dear Steve and Shirley, I’m in my late 30s and I’m dating a man that I met at church. I found out that he talked to our pastor about me and the pastor hinted that he might be ready to propose. I got excited and decided it was time to take our relationship to the next level, meaning it was time for sex. We have been together for six months and we were friends for 2 years before we started dating. We haven’t had sex, but we sleep in the same bed a lot and I like to sleep in my underwear...............

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Why Must He Continue To Text Other Women Jul 21, 2020

Show notes

Dear Steve and Shirley, I’ve been with my husband for 6 years and we’ve been married for 2 years. I have myself to blame for what I’m going through now, because it was an issue before we got married. My husband has a problem with texting and talking to other females. When I’ve addressed the issue with him, he always says “Nothing is wrong with texting and talking, as long as I’m not crossing the line or trying to date anybody.” I believe that if one of the women he talks to or texts comes on to him, that he will take them up on the offer..............

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