Strawberry Letter

Dear Steve and Shirley, let’s get right to it. Here's my dilemma… I’m a 38 year old woman and I've never wanted to have children. Five years ago, I was in a great relationship and we were talking about getting married, but he wanted children and I did not. So we mutually decided to end our relationship. We could not deny that we were still in love with each other, so two years after we broke up, we reconnected and have been seeing each other off and on since then.......... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I’ve been in an “entanglement” with this pastor that I met 8 months ago. My office shared a parking lot with his church and he always greeted me with “Hello brown sugar.” I eventually told him my name because he’s married and I did not want appear to be flirting with a married man and a man of God. I didn’t entertain him at first but then he found me on social media and he started in-boxing me, telling me how lovely I am and how good I smell when I pass by him................ Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

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. Our bedrooms are on opposite sides of my condo so I rarely see him because of our work schedules and his social life............... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

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..................... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

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 travel extensively with one of them................. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

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 getting her credit straight so creditors will stop calling her................... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

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 complete our annual taxes and that’s when it started................ Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

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 scar tissue from the surgery, so it could not be reversed................. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

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 begged me to forgive her and I did, but things did not go back to normal in our marriage............... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

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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 their lives................ Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

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 phone............... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

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 close................ Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

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 cheating, but I always thought he wasn’t the type to do that................. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

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........................ Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

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. We quickly went from being casual friends to meeting up for sex....................... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

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 of the time and he doesn’t................... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

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 sex................. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

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 spiritual fast together, the sex was amazing, and we had the best conversations................. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

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 guest room.................. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

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 dollar store and she dresses like she’s my age.................. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

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 and he was still single and he still wanted me............ Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

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 eager to experience it. We walked thru the cabana area and out onto the beach filled with other naked people, mostly couples............ Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

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 about us all being under one roof, because I had an affair with the oldest daughter.................... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

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 the graveyard shift a lot and so has my crew........... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

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 wine. We had chocolate and vanilla gelato for dessert.................. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

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 at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I am a 44 year old woman and I’ve been attending a church in my city for about 7 months now. It’s a small church and I love the members and I am truly blessed weekly by the beautiful sermons the pastor preaches. The pastor is my age, single and fine. After I began attending the church, the pastor and I became friends on social media, which wasn’t unusual because he’s big on promoting the church through social media and, like I said, he’s single.................. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I’ve been married for 22 years and I have a big problem with my husband. My husband’s co-worker recently bought a motorcycle and my husband wants one, so he showed me pictures of the motorcycle on his phone. As I swiped through the pictures, my husband walked outside, so I kept swiping thru his pictures. I went as far back as March and came across a video of my husband, naked.............. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I’m a 39 year old black man, married to a beautiful black woman and we have a 10 year old son. We have been married for 11 years and over the years, I’ve fallen short of being a great husband. I struggled to stay faithful and I slipped a few times and started sexting and having phone sex with women I met online. It’s not my wife’s fault that I did what I did, but she has changed since we got married................... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I’m a 28 year old black man serving in the United States Army and I’m doing quite well for myself and it’s causing a problem with my love life. I’m hesitant when it comes to dating because I have been meeting the wrong types of women. I am ready to settle down start a family, but I seem to attract female gold diggers............. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I’m a single mom and I met a great guy at work. We dealt with each other for a month and the sex was really good, but I found out he was married. One day, while we were in his car having sex in the parking lot at work, I asked him to turn on the air conditioner so we could cool off. He cranked the car up and his Bluetooth was connected to his phone, so we listened to some 90s slow jams and kept on having sex................... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, my husband and I have been together for 9 years, and married for 8. One year after we met, I got pregnant with our first child, so we got married right away. He’s an excellent provider and great father, but over the years, he’s started treating me like I’m his daughter. I was 22 when we met and he’s 16 years older than I am. I have given everything to this man and he fails to see that I’m a grown woman now............. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, my marriage has been very rocky and it has gotten worse. My wife and I had four kids in a short period of time, so it was stressful at home with small kids running around. I got a really good job to take care of the family, so my wife could finish her degree. My wife got her degree and she started working when our youngest child started school. That’s when things went from bad to worse in our marriage................ Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I'm a 36 year old woman who just found out that I'm pregnant by my co-worker’s son. Her son is 24 and I met him at her birthday party earlier this year. We were standing around and I heard him say he was going to smoke and I told him that’s just what I needed to get the party started. He had a bag of really good weed so I asked him if he could bring me some later in the week. It’s legal, but I’ve never bought it myself. He called me the next day and said he was ready to drop off my package................. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I’m a 39 year old divorced man and I’m the head coach of a high school girls basketball team. My female best friend works with me as my assistant coach. We met 7 years ago and bonded over our love of basketball. She’s a single mom and a straight up tomboy. She wears sweatsuits and sneakers all the time, no makeup and her long hair is always up in a ponytail. I joke with her about being more feminine but she said she’s sworn off dating for now, because her child’s father broke her heart................. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I got accepted into medical school and my sister wanted to celebrate by throwing me small party. I drove 3 hours to her house, for a quick overnight trip. My boyfriend had to work so he couldn’t go. We had food and drinks out by the pool and my ex-boyfriend from 20 years ago showed up. We’ve stayed in touch over the years and it was good to see him. I did 3 tequila shots and I had champagne too, but I wasn’t drunk............. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I am a 28 year old man and I need your advice because the only way I know how to solve a problem like mine, is with my fists. My best friend since college started dating my sister a year ago. I wasn't cool with it at first, but he came to me first and promised me he'd take good care of her because he knows I don’t play about my sister. My sister was happy, so I was happy............... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I was a faithful and committed wife to an undeserving man for 3 years before I decided to flip the script on him. My soon to be ex-husband and I dated back when we were in college and we reconnected 5 years ago. We got married three years ago and a few months after our wedding, I found out that he had a girlfriend and a newborn baby. He admitted it after the girl came to our house.............. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I'm going to dive straight in. I’m a 28 year old father of 3 daughters, by 3 different women and my girlfriend’s pregnant now. The problem is, I’m trying to be the best father for the girls and best possible sidepiece for all of the mamas. I have a special bond with all of them and I have to have sex with them, if I want to or not, so they won’t put me on child support. If one of the mamas gets angry with me, I have to put in overtime with her and make sure I spoil her more than usual.............. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I’m currently living with my mom because of a back injury I got a few years ago. I had to humble myself and ask her if I could stay with her temporarily, after I lost my job. She said I could stay there until I found someone that’s crazy enough to hire me. She is not concerned about my health at all. She calls me lazy when I’m having a bad day and can’t help her out around the house. She’s even told me if I didn’t have such saggy breasts, I’d have a man by now and I’d be his responsibility................ Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I’m 25 years old and I am in big trouble with my girlfriend’s parents. My girlfriend and I got pretty intense in the bedroom last week and I pulled out my phone and started recording us. It was dark in the room, so the video was not that good, but I kept it anyway because I love to hear my girlfriend’s whimpering and how softly she says my name........................... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I am a 41 year old married woman and my husband and I are at odds. Since the pandemic began, he has been growing his hair out and I am not a fan of it at all. He hasn’t shaved in weeks and he hasn’t had a haircut in almost 6 months. He looks like a darn grizzly bear and it’s disgusting. He says he’s waiting to see how big his afro can get because he’s never grown it out before............. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, my husband and I have been together 7 years and he’s always treated me as a queen and he truly values me and our marriage. He accepted my daughter as his own from the beginning when she was an infant. I am 29 and my mom was the best single mother she could possibly be and I got a lot of my independence and determination to succeed from her............... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I am a 51 year old male who is currently going through a divorce. I was married for 28 years and we have both committed adultery and done things in our marriage that I’m not proud of. She has degraded me and humiliated me as a man for years. We have 2 teenagers and initially they both asked the judge to live with me and they stopped talking to their mom............ Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I am a 38 year old wife and mother of 4 beautiful daughters. My husband and I have been together for 18 years and married for 10. We have been living separately for the last 3 years because my husband accused me of cheating in the craziest way. Less than a year after our last daughter was born, he set up a tape recorder in our home to catch me cheating. He told me about the recording and then played the tape for me........................ Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I’m a 38 year old married man and I need your advice on how to handle my wife’s ex-boyfriend. We all go to the same church and we started having Zoom service for those of us that don’t want to physically go back to church yet. My wife and was having trouble with our internet connection a few weeks ago and I noticed some of the members laughing. I wasn’t sure if they were laughing at my wife, so I let it slide................. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I’m writing this letter to get some advice on how to handle my sister and her new husband. My sister called to let me know she eloped and she’s happily married now. I could not believe it. Four years ago, she met a guy at a restaurant and she started hanging out with him. He told her he was bisexual and she didn’t have a problem with that. As her brother, I told her she should not have married him because he's obviously confused on what he wants............... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, my boyfriend and I are both in our mid 50s. We have been dating almost a year and are very much in love with one another. Our sex life has its hills and valleys due to his health conditions and his hygiene. He’s on medication and we got it regulated, but we can’t seem to get past his hygiene issues. Before bedtime, I like to take a nice, hot bath or a shower and I’ll usually invite him to join me. He never does............. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I’m a 43 year old man and I’m a manager at my job. I have a new regional director that will be working in our office. We are both black men but he’s older than I am and he has a PhD that he brags on often. When he first got there, it was hard to warm up to him because he’s so entitled and thinks he is better than all of us in the office. Then things started getting tense when he began to critique the employees on my team. I let it slide and then he critiqued me............. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.