Strawberry Letter

Dear Steve and Shirley, I’m a 34 year old divorced, former model and beauty pageant winner. 5 years ago, I met and married the most perfect man. My husband is the CEO of a major company so we had an ideal lifestyle. I was young, wealthy and beautiful, with a passion for bad boys. I went to the gym daily, and a year ago, I met a man that was my age, with the best body I had seen in my life. I start...

Dear Steve and Shirley, my girlfriend and I have been together for 4 years and we had a normal relationship, having great sex on the regular, until two weeks ago. She started tripping about us having sex and we’re not married, but she lives with me, which also goes against the Bible. We were conflicted about it, but she moved in anyway. After having sex with her for 4 years straight, I am doing my...

Dear Steve and Shirley, I'm a 29 year old workaholic and I don’t have time to date, so I met my boyfriend on Tinder. We met two years ago and were good friends until New Year’s Eve, when he asked me to be his girlfriend. We hung out early in the evening, but he brought in the new year with his friends that were in town for the holidays............ Learn more about your ad-choices at https://www.ih...

Dear Steve and Shirley, I’m 28 years old and my fiancé is 35. We have a baby on the way and I recently moved across the country to be with him. Now that I’m living in his home, I’m not sure that I am making the right choice and I’m questioning whether or not I should marry him. When it comes to his family, there is an open door policy with his family. They come and go as they please and his sister...

Dear Steve and Shirley, I’m in my mid 30s. I’ve been married 13 years and we have 4 kids. In the beginning of our marriage, I was hardheaded and I had a lot of growing up to do. Seven years after we got married, I had an affair and my wife ended up catching us in the act, in my car. I fought hard to get my wife back and since then, I have been the ideal husband and father............... Learn more...

Dear Steve and Shirley, I am a 30 year old single female and last year, I moved back to my hometown. I got an apartment in a nice area of town and my community has a pool and a walking trail, so I’ve been using them both since the weather is nice. Shortly after I moved in, I met an older male neighbor and he’s 71 and recently divorced. Whenever I run into him, he flirts with me and I jokingly flir...

Dear Steve and Shirley, I am a 63 year old black woman and I’ve never been married and I don’t have any children. I was raised to believe sex outside of marriage was wrong, so I didn’t have sex until I was 32 years old. It was never that exciting to me, so I did not put much effort into having a great sex life. I always met and dated great guys, but they would all tell me that I had no passion or...

Dear Steve and Shirley, I’m back… after listening to all the advice you guys had, it lifted my spirits a little bit. Even J. Anthony Brown and Tommy were trying to help. But I’ve had more drama and my stress level is even higher. Steve, I thought I still had some player left in me, but no, I don’t. My wife’s niece still comes to the house to cook, but I steer clear of her. I have stayed in the bas...

Dear Steve and Shirley, I am 49 year old, divorced woman with 2 grown children. Two years ago, I prayed that God send me a real good man and life partner. I was dating with a purpose and I had a list of non-negotiables and must-haves. Six months into praying and dating, I met the most incredible man and he checked off nine of the ten boxes on my list. He lives in a different state, so either I vis...

Dear Steve and Shirley, I’m a 56 year old man with lots of swag and I’ve had fine women all my life. Eight years ago, I decided it was time to get married and I found a good woman to settle down with. I’ve always fooled around with Lotto and bought scratch-offs and a year ago, I got lucky and won $800K. My wife and I retired, paid everything off and traveled a little bit. My wife’s 26-year-old nie...

Dear Steve and Shirley, I'm a married man but I have not been happily married in a while. I have no intention of leaving my wife and I’m not a cheater. I own a small bar downtown and my best employee is also my worst employee. She’s been with me for so long, that I’ve overlooked her raunchy behavior for years. She is a hoodrat and I knew that when I hired her as a bartender. This was supposed to b...

Dear Steve and Shirley, I truly embarrassed myself and I want to pack up and move out of town. I live alone in a quaint little area of town and I am the only black resident on the street. My neighbors and I sit on our front porches in the evening and laugh and talk to each other to pass the time. The other evening, as I was sitting on my porch, I noticed that my azaleas were blooming, so I decided...

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Dear Steve and Shirley, I'm a 37 year old married man with the most perfect wife a man could ever ask for. She accepted me with all my flaws and we never argue. Instead, she calls me out on my BS and we talk things through logically. I have a female friend that is single and bitter and whenever I brag about my great marriage, she always throws shade. She always says that my wife is hiding somethin...

Dear Steve and Shirley, I am a 24 year old woman who’s dating a 28 year old man. Our relationship is great, but I’m holding a secret that could start a war within our social group. Here’s my problem, my boyfriend’s best friend is a pervert. Two years ago, he told me that I didn’t need to wear the jeans I had on anymore because he couldn’t keep his eyes off my booty. I told him that he was being in...

Dear Steve and Shirley, I have been with a liar for 7 years and I thought we had been married for 3 years. When we first met, he told me that he is an only child. 3 months into our relationship, I went by his mom’s house to drop something off for him and there was a woman sitting on the porch with 2 little girls. I got home and asked my man who the woman and the girls were. He said it was his sist...

Dear Steve and Shirley, I am a 30 year old man and I have been dating a new girl for about 3 months. Intimacy came after we had known each other for at least a month. I would sleep over at her house or she’d stay at mine. One evening in late March, we were watching the news and heard about the mandatory stay-at-home order. We decided that she would stay at my house for a while until things got bac...

Dear Steve and Shirley, I am a married woman in my mid-forties and my husband is too. We’ve been together a total of five years and we’ve been married three years. Early on, he explained that he had some medical issues that sometimes kept him from having sex. When we got married, we had only had sex once, but he had found other ways to please me, so I was happy and our marriage was great. I hoped...

Dear Steve and Shirley, I am a happily married woman in my mid-thirties and my husband and I have a son and a daughter. My son is 15 years old and my daughter is 8 years old. We have all been cooped up in the house, but my son has found a new way to keep himself occupied. I found out that he watches porn on his phone. He’s been up in his room, day and night and I was worried about him so I barged...

Dear Steve and Shirley, I am a 57 year old married woman and I have been married for 25 years. It’s been an agonizing marriage because my husband has cheated on me several times with many different women. He got caught most of the time and I would act a fool and threaten the females, then he’d apologize and promise to stop cheating and I’d believe him........... Learn more about your ad-choices at...

Dear Steve and Shirley, I have been with my fiancé for five years and I’m looking forward to a fabulous fall wedding with him. I have one problem that has been bothering me and I need your advice. I started having vivid sexual dreams about one of my fiancé’s best friends, about 2 months ago. I’ve even started fantasizing about him when I’m having sex with my fiancé and I have to concentrate on not...

Dear Steve and Shirley, I have an old friend that I’ve been holding a grudge against for 3 years. She was one of my best friends until she ended up sleeping with my boyfriend. She and my boyfriend were good friends too and whenever he and I had problems in our relationship, he would run to her to tell his side of the story. A few times he got so mad that he left me and stayed overnight with her be...

Dear Steve and Shirley, I’ve been in a relationship for a little over a year with a wonderful man that I met online. We’re both in our forties and never been married. He is on the shy side and hasn’t dated a lot. When we met, I could tell that he was a lot more laid back than me and he did not have much experience with women, so I was patient with him and he started opening up more. I was also pat...

Dear Steve and Shirley, I've been divorced for four years and my 7 year old child is caught up in a dysfunctional mess with me and my ex-husband. After my divorce, I found out that my older sister was having an affair with my husband. Throughout the divorce, she was my rock and I turned to her for advice, since she’d been divorced 3 times. All of the signs were there that they could have been mess...

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...