Strawberry Letter

Dear Steve and Shirley, I’m divorced and dating again. I have a special friend that is in a complicated marriage and I slipped up and had sex with him a few weeks ago. Since then, he has been hooked on me and he slides by my house whenever he can. We have unbelievable chemistry in the bedroom but I still try to keep everything in perspective because he is married and I know his wife..................

Dear Steve and Shirley, I’ve been married to my best friend for a very long time. He and I do everything together since we retired this year. We have 2 daughters and we visit them often because our oldest daughter just had her first baby with her husband and our youngest is getting ready for her wedding next year. We can not stand this guy she’s marrying, but we’d never tell her......................

Dear Steve and Shirley, I’m a 33 year old recently single woman and I was in a tumultuous relationship with a wimpy man. We’ve been on again, off again and he’s inconsolable whenever we are apart. We broke up over the way he washed the dishes and he’s been calling me non-stop to plead his case. He’s called my mom crying and she wants me to get back with him so she can get out of our drama. This ma...

Dear Steve and Shirley, I’m in my early thirties and I’m eager to meet a nice man and settle down one day. But in meantime and in-between time, I was keeping myself entertained in online chat rooms and online dating. I met a man that I paired perfectly with and his profile said he was 6’2” and athletic. His picture was nice but not really my type. We started chatting offline and would stay on the...

Dear Steve and Shirley, I was released from state prison a few months ago. While in prison for 23 months, I thought my girlfriend had my back and we’d get married when I came home. Boy was I wrong and I came home to a situation that was worse than prison. I was released to my own home, with my girlfriend, who has been staying in my home while I was in prison. It was supposed to be a joyous homecom...

Dear Steve and Shirley, I’ve been dating a very handsome and physically fit man for 2 years and we’ve reached a roadblock in our relationship. He’s never been married and he doesn’t have any children. When we met, he was glad I had children because he didn’t want any. He loves my children and treats them well so that made me love him more. I had a child when I was 16 years old and another when I w...

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Dear Steve and Shirley, I’m 58 and on my second marriage to a man that I only knew 7 months before we got married. He swept me off my feet after I met him at church. We actually met online but we agreed to have our first face to face encounter at church. We spent that entire first day together and into the night. He said he was an expert on beautiful souls and mine was the brightest he’d seen in y...

Dear Steve and Shirley, my husband and I are both 28 years old and we have a 2 year old daughter. He’s white and I’m black. He is a semi-pro athlete and we live in a nice community of young couples. I work in hospital administration and we met when he came to speak to our pediatrics unit. We will be married a year in December, if we make it, because my husband really showed out this summer...........

Dear Steve and Shirley, I’m in a relationship with a man that is a contributor on our local news. He’s also an auctioneer at an auto auction. He makes all of his money by talking. Whenever we go to dinner or anywhere out in public, he holds a conversation with others and I’m standing there nudging him to leave folks alone. All during my reality shows, he asks me who is who and why the people act l...

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Dear Steve and Shirley, I am married to a die-hard football fan and we met in college. We went to an HBCU and for years, we have tailgated with friends and family before the home games. I had a minor surgery so I had to miss the first home game. When we tailgate, we take our RV to the stadium, hook our deep fryer and our grill and get to cooking early in the morning. It’s what we do..................

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Dear Steve and Shirley, I’m a wife and a mother of 2 young kids. I worked full-time and I taught an evening class at the college in my town. A friend’s husband works at the college and he hooked me up with the job. I planned to teach full-time at the school, so I quit my other job. But after a strange turn of events, I am jobless and in hot water with my husband.......................................

Dear Shirley and Steve I am a successful 34 year old married man and I love my wife, but I’m miserable at home. My wife and I met just before Covid and we’ve been married for a year. Our marriage was great until recently and it’s because of my 28 year old stepson that won’t move out of our home. My wife is sixteen years older than I am. When we met, her man child was living with her and she told m...

Dear Steve and Shirley, I am a 47 year old woman and I’m with a man that is out of my league. Don’t get me wrong, I have a great job and I’m educated but my past is sketchy. He’s a surgeon and his daughter just finished medical school. He’s been divorced for 6 years and he’s ready to settle down with me. We met on a site for professional singles and we’ve been dating for almost a year. I’ve never...

Dear Steve and Shirley, I am a 46 year old married woman and I am having an affair with my pastor. He’s new to our city so I was chosen to show him around and help him get acclimated. He’s a married man with 2 children but his wife and children decided to stay put until their oldest daughter graduated high school. So, he was new in town and bored out of his mind. We started hanging out a lot and h...

Dear Steve and Shirley, I grew up in a two-parent home and both of my parents earned college degrees and worked hard to provide a good life for me and my siblings. I have a college degree as well and I’ve been married for over 20 years to a great woman and we have two teenagers. My teenagers are well mannered and really smart kids. So, here’s my problem… I met my wife in college and fell in love w...

Dear Steve and Shirley, I’m a 31 year old single female and I just broke up with my boyfriend after 2 years of dating. I gave him all I could in our 2 years of dating and he didn’t show up for me in a way that proved to me that he wanted to get married. He kept on going to the club and hanging out in the strip club. I couldn’t get him to spend time with me on the weekends and I was done with fight...

Dear Steve and Shirley, I’m a 52 year old married woman but my husband and I have been at odds for a few years because he is a cheater. I never caught him but all of his mannerisms changed and we stopped being intimate. The arguments got so bad that I stopped talking to him altogether and focused more on my kids and my promotion at work............................................. See omnystudio.c...

Dear Steve and Shirley, I’m 30 and my fiancé is 28 years old. We have been together 2 years and he proposed 3 months ago. I’ve held out on intimacy with him until l got a commitment and he did not have a problem with that. The night that I got the ring, I gave in and we had sex that night. It was not what I expected at all. I’d seen him naked a million times and I knew what he was working with, bu...

  Dear Steve and Shirley, I’m a 60 year old single mother. My son is 32 and he has been a single father since his first wife passed away 4 years ago. My granddaughter is 14 years old and she’s with me during the week and she goes back to her dad’s house on the weekend. My son has started back dating and he wants to be married again. He says he doesn’t function well as a single man....................

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...

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Dear Steve and Shirley, I’ve been dating a musician for almost 2 years and he’s so different from anyone I’ve ever dated. We met at an engagement party and the bride-to-be begged me to give him a chance. He is a black hippie that sings R&B cover songs. Wrap your mind around that. He has a 3 piece band, all females. He had the most beautiful smile and I was attracted to his fluffy beard so I de...