Strawberry Letter

Dear Steve and Shirley, I'm a 44 year old mother and I allowed my 24 year old son to move back home after college. I had hoped that he would find a great job and get his own place, but he wasn’t so lucky, so I told him he could come home temporarily. My house rules are the same as when he was in high school. He’s expected to keep the house clean and the lawn looking good, in exchange for housing....

Dear Steve and Shirley, I am a 58 year old widow and I’ve been dating my current man for the past 10 years. He refers to me as his wife and most people think we are married. Truth is, I haven’t married him because I still get my deceased husband’s pension and he is okay with that. Before Covid-19, we were inseparable. We don’t live together, but he was with me day and night..................... Le...

Dear Steve and Shirley, I’m a 29 year old woman with a great job and a great body, pretty face, and 3 boyfriends. One boyfriend is 38 and he’s an oil company executive. One is a 39 year old police detective. The third one is only 21 and he’s a manager at a retail store. They are all good financial providers and the youngest one is muscular and very handsome. The two older ones spoil me and I trave...

Dear Steve and Shirley, I’ve been living with my current girlfriend for 2 years and everything is great until we start talking about our finances. I’ve worked since I was a kid and now all I want to do is save money and keep my small black-owned business afloat. My girlfriend is not good with money and she’s lived check-to-check since I’ve known her. I’ve talked to her about saving money and getti...

Dear Steve and Shirley, I am a 55 year old, married, successful woman, sleeping with my son’s best friend. He and my son have been the best of friends since the second grade and now they’re both 27 years old. The best friend, who we’ll call David, has been working with me for a year, as my accountant. I let the rest of my employees work from home during Covid-19, but David came into the office to...

Dear Steve and Shirley, I am a 53-year-old man and my fiancé is 35. We’ve been together for 4 years and from the beginning, she told me she wanted to be a mother. I was married before and I’ve got 3 children… and I’ve had a vasectomy. As our relationship got serious, I told her I could get my vasectomy reversed and I would give her a baby. I visited my doctor and I was told that I had a bit of sca...

Dear Steve and Shirley, I was married for 4 years and at first, my marriage was great and my wife was sexy, classy and ratchet so we had a lot of fun together. She was a very sexual woman so she talked me in to going to a swingers group. My wife liked it so much that she started having an affair with one of the guys she’d had sex with at the swingers party. I found out and I was so hurt. She begge...

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Dear Steve and Shirley, I’m a 30 year old black man and I grew up in a middle class family, but I had a lot of friends. A lot of my friends were from a different background because I’d meet them playing sports or hanging out. I went to college and came back home and realized I’d outgrown a lot of my friends because they were still living at home with their parents and didn’t have a real plan for t...

Dear Steve and Shirley, I have been married for 25 years to my soulmate and we had a great life, until 3 years ago when I caught him cheating. One night when he was supposedly hanging out with his boys, he called me and said he was too drunk to drive home. I offered to go get him, but he said he was going to sleep it off and come home soon. I called to check on him at 6am and a woman answered his...

Dear Steve and Shirley, I’m a 40 year old married woman that got married in September and I’m already having problems. I met a great man in July and we had an instant connection and we fell in love quickly. We caught the Coronavirus around the same time so we bonded over that. We were inseparable… if he was using the bathroom, I’d sit in there and talk to him and vice versa. We were just that clos...

Dear Steve and Shirley, I need your advice on how to move past being hurt by my husband. My husband cheated on me several years ago and although I love him deeply, I haven’t been able to move past the cheating. The most hurtful part is that he waited till after our 20th wedding anniversary to start having an affair and it lasted a very long time. I was not blind to the fact that he could’ve been c...

Dear Steve and Shirley, I have been with my boyfriend for 7 years now and he was raised by his father and his father’s girlfriend has been a mother figure to him for the past 15 years. His father is a sweetheart and his girlfriend is nice but I’ve always thought she is kind of weird. She had a birthday recently and my boyfriend and I were invited over to have cake and sing happy birthday.............

Dear Steve and Shirley, My life is a mess and it all started a year ago when I moved in with my aunt to help her after she broke her leg. I was running errands for her one day and I met a man at the grocery store and we started talking and he was flirting up a storm so I gave him my phone number. We started off talking a lot and it helped me get through the rough days as a caretaker for my aunt. W...

Dear Steve and Shirley, I’m an attractive 45 year old independent woman and I’ve been in a relationship with a 41 year old man for a year. We don’t live together because I’m not ready for all of that and we’ve been arguing a lot lately. He’s a great man and for the first time in a very long time, I’m faithful to one guy. He is great in the bedroom, but his libido doesn’t match mine. I want sex all...

Dear Steve and Shirley, I’m in my early thirties and single but I’m finally ready to settle down again, after dating a mentally abusive man for close to four years. I’ve always thought I’d fall in love and get married before I was 30, but then I realized that this is just a fairytale because dating is very different now. Every guy I met this year was a playboy and wanted to casually date and have...

Dear Steve and Shirley, I’m a 56 year old woman with a lot of past trauma and family issues so I’ve been single a long time. I got out of my comfort zone though, and I opened my heart to a man that had just got out of prison and he had a history of drug abuse. We dated for 4 months and things were great. He was living with his brother but he’d come over and cook for me and do yardwork. We did a sp...

Dear Steve and Shirley, I need your input please. I live in the UK, right outside of London and I love your show. I have known this gentleman friend of mine for 2 years. We have a great friendship so a few weeks ago, I invited him over for the weekend. It started out as a great meet-up and I was glad to finally get to spend time with him. I asked him if he wanted to share my bed or sleep in my gue...

Dear Steve and Shirley, I’m a 23 year old woman, living with my grandparents and I have a major problem with them. Recently my grandfather has been pressuring me to have a good relationship with my siblings and I’ve told him several times I’m not interested in getting to know them better. I know this sounds harsh, but I can explain. My birth mother is a hood rat, kitchen beautician, working at the...

Dear Steve and Shirley, I dated a guy off and on for about 3 years but we never had sexual relations because I was having myself a good time dating several men at once and I was celibate. He was a perfect gentleman and had every quality that I prayed for in a man, but I wasn’t ready to settle down. Now that I’m 29, I decided it was time. My heart lead me back to the guy I’d been casually dating an...

Dear Steve and Shirley, my husband and I were on vacation and strolling along the beach one night and discovered a portion of the beach that was for nudists. My husband thought it would be fun to experience it, so we walked over to a cabana like entrance. There was a greeter that told us to take our clothes off and place them in the cubbyholes along the walls. I was reluctant, but my husband was e...

Dear Steve and Shirley, I'm a 57 year old married man and I’m on my second marriage. My wife has two daughters from a previous marriage and they’re both grown and live in different cities. The oldest daughter is 29 now and she has a 1 year old son. My wife is looking forward to Thanksgiving because she will have the girls home and she can spend quality time with her grandson, but I’m not excited a...

Dear Steve and Shirley, I have an employee that is married to a crazy woman that constantly harasses me. She has it in her head that her husband and I have something going on. I am a manager of an essential business and my employees all have specialized skills that are in demand. Therefore, I rely heavily on them to keep my business going. We are currently backed up on orders, so I’ve been working...

Dear Steve and Shirley, I’m a 51 year old single male and I was dating one of the sweetest women I’d ever met. I spent a lot of time trying to impress her by pretending to be a foodie and acting like I’m into fine wines, because that’s what she likes. Sunday, we went to an Italian restaurant and we shared a pasta dish that had a heavy cream sauce with cheese and asparagus, and we drank a bottle of...

Dear Steve and Shirley, I’m a 30 year old man, dating a 25 year old woman. We’ve been together for 4 months and things just got ugly between us. She moved to the United States three years ago and her parents live in Africa. She came to the states by herself to attend college and she’s done quite well for herself. She’s not like the average 25 year old…............. Learn more about your ad-choices...