Strawberry Letter

Dear Steve and Shirley, I’m a 31 year old married woman and my marriage is basically over. A year ago, a 24 year old female called me and said she’d been sleeping with my husband and sent me a picture of him in her bed. Right after that, I had to be quarantined with this man, so I made the best of it. By December, I had started having virtual counseling sessions with my pastor. He was one of the f...

Dear Steve and Shirley, I met the love of my life 7 years ago and I was 21 years old at the time. He’s 3 years older than me and had already had a child. He was my first everything and he influenced everything I did. I overlooked a lot of things he did because I was young and crazy in love. He would be intimate with the mother of his child and he didn’t try to hide it. It made me feel like I wasn’...

Dear Steve and Shirley, I’m 38 and I married my beautiful wife 5 years ago. We both have great jobs and we bought a big house for our family. When we got married, she came with 3 kids and her nephew that she’s raising for her sister. No problem, I did not have children and I loved being a father all of a sudden. I have a job that involves a lot of travel and for the past year, I’ve been out workin...

Dear Steve and Shirley, I’ve been married for 2 years and when I met my husband four years ago, he had just gotten divorced and he was in a bitter custody battle with his ex-wife. His daughter is very sweet and she loves her dad, but the ex-wife is dead set on her not having a relationship with her dad. When we met, he had to limit communication with his ex because she told everybody he kept calli...

Dear Steve and Shirley, I am a 36 year old married woman and my husband just turned 40 so we went on a weekend getaway to Las Vegas with another married couple that we have known for years. We got to our hotel suite and we were drinking and eating and having a good time, just the 4 of us. The guys went down to the bar around 11pm for a nightcap. I was so tipsy and tired, that I decided to lie acro...

Dear Steve and Shirley, I am a 34 year old woman grieving the loss of my 77 year old best friend and sugar daddy that had been in my life since I was 19. He was also my father’s closest friend so we kept our relationship a secret for obvious reasons. When it all started, he was married to a woman that I looked up to. She was beautiful and classy and he turned me into her, with all of the nice gift...

Dear Steve and Shirley, I am a 28 year old woman and I’ve been having bad luck on the dating scene. Finally, I met someone and thought he was great. Emotionally, he fulfilled my needs and he planned the best dates. We formed a bond over the fact that we were both tired of dating and being disappointed. After dating for 2 months, we decided to take things to the next level and we had sex..............

Dear Steve and Shirley, I’ve been with my girlfriend for close to a year and she has a problem with talking behind my back. I noticed a change in how her friends greeted me and acted around me but I didn’t think much of it, until I found out why they were doing that. One night my girl got an attitude with me because I was playing a video game and she wanted to argue about it. She started texting s...

Dear Steve and Shirley, I have been married for 12 years and my husband and I are in our mid 30s and are regulars at a local bar by our house. We’ve met a lot of great people at this bar and look forward to seeing them weekly for karaoke night. I like the sense of community we have there and we can hang out with the other couples we’ve befriended............... Learn more about your ad-choices at...

Dear Steve and Shirley, I’m a 29 year old woman and I’ve been engaged for 2 years. I’ve never questioned my man’s loyalty to me and in the 5 years total that we’ve been together, I don’t think he’s ever cheated on me. We live together and I have all of his passwords to his phones, social media accounts and his checking account. He has all of mine too............. Learn more about your ad-choices a...

Dear Steve and Shirley, I have been friends with a great guy for three years and we have become the best of friends with the best sexual chemistry. Our sex is off the chain. He dates other women but he’s always said that he wouldn't get in a relationship without letting me meet the female and giving him my blessing. We never talked about us being in a relationship so I gave up hope early on. He fo...

Dear Steve and Shirley, about a year ago I left my home church to join another church. I was dating the church’s drummer and he invited me to join. I fell in love with the atmosphere of the church and the senior pastor was really good. When I joined, I was asked to help put together a praise dance team. I enlisted the help of the associate pastor to help me. The associate pastor is only 3 years ol...

Dear Steve and Shirley, I may need Tommy and J to offer some advice with this one, if you don’t mind, since they’re the side piece experts on the show. I have been a proud side chick to a married man for over 7 years. I knew what was up when we met and I was fine with it. I was happy to provide laughter, fun times and a lot of great sex once or twice a week. For the most part, I’ve held up my end...

Dear Steve and Shirley, I was a single and attractive, 34 year old woman, losing hope at finding love. I grew tired of the dating cycle and I decided that I would not have sex again until I was married. I prayed and practiced celibacy and a year later, I met the man of my dreams. He is handsome, educated, gainfully employed and he loves the Lord. I fell hard for this man and a year after we met, w...

Dear Steve and Shirley, I worked from home as a corporate sales leader for 5 years. In February, I quit my job to do a podcast with 2 of my best girlfriends. Let me give you a little backstory… My husband and I met in college and got married when we were 24 and started a family. We had our first child when we were 25 and our second child on my 27th birthday. I have a degree in Mass Communications...

Dear Steve and Shirley, I am a 32 year old single mother with one child and I’m pregnant with my second child. I’m pregnant by my best friend, who happens to be married. We’ve been friends with benefits for almost to 10 years and his wife thinks we’re just best friends, so she’s accepted me as part of the family. She’s aware that I’m pregnant but thinks it’s my ex-boyfriend’s baby. I’ve told her h...

Dear Steve and Shirley, I am in need of some sound advice. I got married 6½ months ago after reuniting with my man. We had an on and off relationship for years and he started seeing a woman that catered to his big personality. She dumped him and he came running back to me. After he begged me to give him another shot, I took him back and we got engaged. As soon as he put the ring on my finger, his...

Dear Steve and Shirley, I’m a 27 year old single female and I just moved to my own place and started a new job. I like my job and I have a few associates that I hang out with after work. There’s one guy that I’m the closest with. He’s 47 and married but unhappy at home. We created a bond and we could tell each other anything, without judgment. The first time we made love, he made me feel like a pr...

Dear Steve and Shirley, I’m going to jump right on in. I cheated on my wife two years ago with a woman that constantly threatened to call my wife when she didn’t get what she wanted. This went on 2 years until I ran out of money and decided to end the affair. This woman called my wife a few days later. I was out, cutting the yard when she called my house and my wife answered.................. Lear...

Dear Steve and Shirley, I’m a 40 year old black female and I’m an office manager at a small business. The owner of the business is an old family friend of my parents. He’s getting pretty old and has had some health issues, so his twin brother is helping out with the day-to-day operations. This older gentleman is in his 70s and he’s very sweet and pleasant. He comes to work overdressed daily in his...

Dear Steve and Shirley, I have been dating a guy for about a year and a half now and I’m concerned that he isn’t motivated to better himself. The first time I spent the night at his house, I made some comments about his neighborhood being kind of ghetto and then I commented on how none of the yards have grass and the houses have burglar bars on the windows and doors. I thought to myself there’s no...

Dear Steve and Shirley, I have been married for five years and it is a second marriage for us both. My issue is my 46 year old step daughter that has been inviting her mother everywhere for years. My husband divorced his first wife in 1987 and his daughter is still including this woman in all of our family functions. The ex-wife is the daughter’s best friend and they do everything together. I don’...

Dear Steve and Shirley, after 18 years of knowing my fiancé, she cut the fool. I’ve been divorced for 21 years and my 4 children are all grown. She’s divorced too so there was never any pressure to get remarried, but I proposed recently because she’s the perfect woman in every way. She was getting her house ready to be sold and move in with me. Her kitchen sink leaked and the disposer didn’t work,...

Dear Steve and Shirley, I believe my wife is tripping for no reason. The other day, we were in the grocery store going down the aisle and there were two women shopping together in front of us. They both had carts full of groceries so as we passed them, I noticed all of the stuff in their baskets. We turned onto the next aisle and my wife pinched me and said she saw what I was staring at. I have to...

Dear Steve and Shirley, for the past year I have been sleeping with my best friend's little sister. When I went to college, I lost all contact with her until we reconnected last year at her brother's 4th of July party. I hadn't seen this woman since she was a young girl and my oh my God she’s aged like fine wine. I’m 14 years older than her but we’re all grown now. The Lord took his time with that...