Strawberry Letter

Dear Steve and Shirley, I am a young, healthy and wise beyond my years single woman, that is a leader to my peers. At my young age, I have found the most handsome and amazing man of my dreams. He is respectful, has a great job, a beautiful home and he treats me like a queen. But here is the problem… well, it’s not a problem for us, it’s more of a problem for our friends and family. I am 22 years o...

Dear Steve and Shirley, I really need your advice for this issue I’m having. I have fallen for someone that I have never met in person. I have heard him speak almost everyday and I'm not sure if he is single, but I would love to meet him in person. I am single and ready to mingle with him if he is available. This guy makes my toes curl when I hear his voice and the icing on the cake is that he is...

Good morning Steve and Shirley, I am 50 year old divorced lady with a 28 year old lover. We’ve been together for two years but I met him when he was in college with my son. He came home a few weekends with my son and he started calling me mom back then. After college, he continued to hang out at the house with my son, so I got used to him being around. Well on Easter Sunday, 2017, things changed i...

Dear Steve and Shirley, my husband acts like an absolute child at times and I can’t deal with it. It’s like having a third child and I am so tired of him embarrassing me. The most recent incident went down over the weekend at my Pastor’s house. We were invited to a barbeque and the pastor was a little late because of a wedding he had to do. There was plenty of food on the grill and we always let t...

Dear Steve and Shirley, I am a 55 year old mother of 3 handsome boys. My youngest son is getting married, but I have an issue with his fiancé and I feel very guilty about it. I hate to be rude, but the girl he is marrying is just not that attractive at all. I know it’s none of my business because he’s the one that has to live with her, but my son is very handsome and I feel like he could do a lot...

Dear Steve and Shirley, I’m a 39 year old Latino woman, married to a 53 year old black man. We’ve been together for 7 years and we’ve been married for 3 years. We met at church and we’re both in the church choir. When we started dating, I saw an edgier side of him. He rode a motorcycle, drank Hennessey on the weekends and he cursed whenever he talked to his friends. It was different from the churc...

Dear Steve and Shirley, I am in my early 30s and I'm dealing with a guy in his mid 30s. We hung out for a couple of months and he was ready to get serious, which meant it was time for me to give up the cookie. From the time I met him, I had a problem with his so-called best friend, who is a female. I’ve tried to understand the relationship and he says it’s nothing, but she spends the night at his...

Dear Steve and Shirley, I’ve been with my girlfriend for 10 years and we’re having our first major issue. When I met my girlfriend, she was new in town, so I introduced her to my group of friends and their wives. There are 4 couples that hang out and we’ve all known each other since college. The wives were all nice enough to my girlfriend but they’ve never included her in “girls night out” or invi...

Dear Steve and Shirley, I am a 27 year old woman and I have a 1 year old son. I met his father almost 2 years ago. When we met, I assumed he was single because he approached me and spent a lot of uninterrupted time with me. Come to find out, he has been in a relationship for 8 years. It was too late to cut him off because I was already pregnant. We argued over and over again about how he lied to m...

Dear Steve and Shirley, I have been married for 25 years and last weekend, my wife and I took a road trip to see my wife’s dad. My wife’s mom passed away 3 years ago so her dad is still adjusting to being alone. Her dad was so happy to see us and he asked my wife to cook his favorite dinner. So when my wife started cooking, my father-in-law slipped outside and was talking to an older lady that had...

Dear Steve and Shirley, you are not going to believe this. I am 30 years old and my longtime girlfriend has an identical twin sister. I can barely tell them apart sometimes. They both have short curly afros, they both have dimples in both cheeks and their bodies are the same. My girlfriend and her twin love to prank me and confuse me since they look so much alike. Their little pranking went too fa...

Dear Steve and Shirley, I have been married for 15 years and my husband is an associate pastor. He has office hours at the church and the church secretary is there from 9am-5pm. I started working part-time because I wanted to buy new furniture. I work in an artsy area of town at a craft store and there are several restaurants in the area. On 2 separate occasions, my husband called me to say he’d b...

Dear Steve and Shirley, 2 years ago, I met the man of my dreams and he loves me, motivates me, and we can’t get enough of each other sexually. We've been talking about marriage and starting a family soon. There’s just one problem. Recently, I’d been thinking a lot about my ex-boyfriend and I decided to call to see how he’s been doing. I also wanted to let him know that I’d found happiness again......

Dear Steve and Shirley, I’m in my early 50s and my husband and I have been married for 7 years. Since the beginning of our union, he knows that I’m able to manage all of our household expenses and he has taken advantage of it. I’ve funded a lot of hair-brained business schemes he’s invested in and lost a lot of money fooling with him. He’s had a string of jobs in leadership positions that I’ve hel...

Dear Steve and Shirley, I was in a relationship with a man for 6 months, but we fell in love quickly and we were living together. He is 36 and I’m 31. He was going through a divorce when we met so I made him wait until the papers were signed before we had sex. He told me that his wife divorced him because he cheated on her multiple times. He told me that he cheated, simply cause his wife had stopp...

Dear Steve and Shirley, a while back I met a man on a dating app and it was supposed to be just a one-night stand. He came over and we had the most explosive sex! After that, we talked all night. He lives out of town and when he got back home, we talked daily and spent hours getting to know each other. He came back to visit me because he was dying to have sex with me.............. Learn more about...

Dear Steve and Shirley I’m a 32 year old married woman and I’d normally never write in to you, but I heard you cover a topic that I’m going through so I’m turning to you for help. It’s about an issue I’ve been having with my husband since the quarantine began. He and I were having sex more than usual and it was getting boring. I wanted to spice things up with role-playing.......... Learn more abou...

Dear Steve and Shirley, I’m a 40 year old black man with a lot of weight in my community. I’m a very well-known businessman and former professional football player. I’ve been married for 10 years and I have 3 children. My wife is very sweet and we never argue or have any issues with our children. Everything is great, except for our sex life. My wife is a good woman that is very reserved in the bed...

Dear Steve and Shirley, I’m 29 years old and my boyfriend is 30 and he’s an idiot. We have been together for 4 years and his ex-girlfriend and I were close friends before her man chose to be with me instead of her. I might have been wrong for dating him, but it felt like the right thing to do at the time. In the beginning, she tried to fight me 3 times and she showed up at my job once and I had he...

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....

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 o...

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” whe...

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 an...

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 w...

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 h...