Strawberry Letter

Dear Steve and Shirley, my 46 year old wife and my 39 year old sister are up to something. My sister recently got a divorce so my wife spent a lot of time comforting her and in the process of doing that, they went on a vacation to Miami. When they got back, my sister was distant and wouldn’t come around. She said she met a great guy and was laying low and keeping her business private. My wife cont...

Dear Steve and Shirley, I am a 32 year old single mom of a 16 year old and I still live at home with my 84 year old father. I have never moved out because I never wanted my daughter to suffer through any hardships or go without having the things she wants and needs. My dad takes good care of us, so that helps me save money. Here’s the problem… I’ve been dating a man for 4 years and we have a great...

Dear Steve and Shirley, I’m in my mid 40s and I’ve been married for 3 years. A month ago, my husband drove me to my hometown for one of my childhood friend’s wedding. We went to visit with my parents before the festivities and then we checked into our hotel. Everything was cool and we were having a good time until later that evening. We went to the rehearsal dinner and I got to see a lot of my old...

Dear Steve and Shirley, I've been married for exactly one year to the devil. My husband is an IT manager and I’m a veterinarian. I celebrated our one-year anniversary and then I went to visit my parents for the weekend. My visit was cut short when I got a call from my neighbor saying there were a lot of cars at my house and she knew I was out of town.................... Learn more about your ad-ch...

Dear Steve and Shirley, I’m a 44 year old married woman and my husband is incarcerated so I’m raising our two sons alone. I get a little help from my husband’s family, but they always complain so I hate asking them for anything. When my husband went in, his job paid out his severance package and that held us over for a year. I got a job but it was hard keeping up with the kids and a job, so my hus...

Dear Steve and Shirley, I’m a 31 year old man and I met a really dope woman at a house party. She’s 30 years old, no kids, with a good job and her own house. I started vibing with her at the party so I asked her out. Two days later, she picked me up for our date and she asked to use my bathroom. She left the bathroom door open and told me to come in. She sat on the counter, whispered a few words i...

Dear Steve and Shirley, I have been married for almost three years now. My husband and I are intimate at least four days every week. I like to keep things hot and spicy, nothing is ever the same in the bed or wherever we chose to do it. I do all that I can to please him and I make sure I am pleased as well. Our sex is always amazing, but, he has confessed to being unfaithful during our entire marr...

Dear Steve and Shirley, I am a 55 year old divorced woman and I met a handsome, slightly older gentleman online. We have a lot of things in common and I found out we know a lot of the same folks. Since my divorce, I’ve put on a few pounds here and there but he doesn’t seem to mind it. When we first started dating in January, I had to spend a few days in the hospital and he called me daily to check...

Dear Steve and Shirley, I am a 39 year old single mother of a 17 year old son. My son's father has never been in his life so I was blessed to have my dad to be a role model for him. My dad passed away in 2018 and since then, my mother moved in with me. She's home with my son daily while I work and she helps him with his virtual classes.................. Learn more about your ad-choices at https://...

Dear Steve and Shirley, I have been with my wife for 13 years but we’ve been married for 9 years. We have three children, ages 4, 7 and 10. During our marriage, I’ve cheated and mis-managed our finances a few times. Whenever I messed up, I fessed up and she was always willing to forgive me and move on. But, when she’s angry with me, she’s just downright nasty. She’s spit on me and thrown things at...

Dear Steve and Shirley, I am a 37 year old married man with one son from a previous marriage and one son with my new wife. I’ve been remarried for almost 4 years and my life is great now. I have a great relationship with my ex-wife and my son is staying with me because he needs a strong male role model in his life. My wife is friendly with my ex-wife and that makes me love her even more. I do beli...

Dear Steve and Shirley, I am happily married and my wife and I have two kids. The problem is I have a female friend from college. My female friend is also married with two kids and she lives in another state. We hardly ever see each other, but we do keep in touch. Over 15 years ago, she and I had sex. My wife knows we were intimate in the past because we all went to the same college. The other day...

Dear Uncle Steve and Aunt Shirley, I am a young female that graduated from high school two years ago. Yeah and I am in a sticky situation. You see after graduation I met a guy on an online app and we texted back and forth and decided to spend some time together. We ended up going on dates and messing around a lot. He is a really great person but he was not the one for me so we ended our fling. We...

Dear Steve and Shirley, a year ago I found out that my husband cheated on me with my sister. We were married for 9 years so it was not unusual for him to have a great relationship with my sis. They joked around and would play fight like they did not like each other. All along I thought it was cute and I had no idea that it was foreplay. I caught them in our garage one day, years ago, behind the ca...

Dear Steve and Shirley, my husband and I have been together for 6 years and married 3. He’s 37 and I’m 31. He’s divorced and has a son and a daughter from his marriage. I absolutely adore them and they spend weekends and summers with us. My husband has always put his children first and I love that about him. He still finds time to spoil me by doing all of the cooking, planning dates for us and sen...

Dear Steve and Shirley, I’m a 57 year old single mother and I am all up in my daughter’s business. My daughter is 31 years old and a professional woman. She’s dating a man that I can’t believe she would ever be attracted to. He is a 40 year old single father with twin sons that are 6 years old. He owns a car wash and makes a good living, but he’s flashy and loves to be the center of attention. He’...

Dear Steve and Shirley, I’m in my late thirties and I found out that my husband of 10 years has a girlfriend on the side. I have been tracking his car for months and he picks her up from work, takes her to dinner and then comes home. I even know where she lives and I’ve sat outside her house and blew the horn and waved at her. She knows who I am, so it’s odd that she’s never mentioned anything to...

Dear Steve and Shirley, I am 35 year old married woman and I have been married for three years, but, I've been with my husband for over 8 years. He was supposed to be a one night stand but he ended up rocking my world and I kept going back for more. He grew on me and I ended up falling in love with him. It's no secret that he fell in love with me first and he loves to tell people how he pursed me...

Dear Steve and Shirley, I’m a 62 year old widow and I live in the great city of Chicago. I was married for 34 years to a wonderful man and he died 3 years ago. Since then, I have secretly fallen in love with my 31 year old Godson. I know I should be ashamed of myself, but I’m not. When my husband first got sick, my Godson is the only person that would check on me and make sure I ate and I was gett...

Dear Steve and Shirley, I am a 49 year old retired businessman. I had a start-up in the early 2000s that did very well and I sold it in a multi-million-dollar deal. I make the majority of my income now from my real estate investments. That’s how I met my 27 year old fiancé. She was renting one of my houses and after three months of her living there, we had sex and I started taking care of her in e...

Dear Steve and Shirley, my husband of 22 years has made a lot of changes in the last 6 months. He’s been in the military since I met him and he retired last year, but he still hangs around with his co-workers. He has always cursed like a sailor because he was a sailor when he was younger. When we had our first child, I asked him to watch what he said around our daughter and he slacked up with usin...

Dear Steve and Shirley, I am a 38 year old woman that has been married for 14 years and we have two children together. I realize when you are married people change over time and sometimes it is not even worth it to try to work things out. I am at that point with my husband. He’s changed into an evil monster. He has always been overprotective, possessive and extremely jealous but in the past few ye...

Dear Steve and Shirley, I need your advice on an issue with my husband. We’ve been married almost 2 years and we are parents of a 7 month old baby girl. I’m a nurse and I work nights, 7pm till 3am. My husband is an optometrist and he had a licensing exam in Maine last month so he had to be gone for 5 days. I suggested that my best friend’s sister babysit while I was at work. She’s 25 now and I’ve...

Dear Steve and Shirley, I’m in my late fifties and I’m dating a man that is a few years younger than I am. We’ve been together for 8 years and it’s been on and off because we live in a small town so everyone is always in everybody’s business. He’s a cheap skate and he knows he doesn’t make enough money to support me and his drinking habit, so I’ve asked him for years to get a better job or a secon...

Dear Steve and Shirley, I met the love of my life 4 years ago right after I got out of a terrible marriage. My woman is educated, very established and drop dead gorgeous. She grew up in the suburbs and I grew up on the other side of the tracks. I’ve assimilated well and I have a great career, but my hood side still comes out when I least expect it. She loved my corporate and hood sides. For the fi...