Strawberry Letter

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.

Dear Steve and Shirley, I’m 56 years old and I’m dating a 61 year old man that is separated from his wife. He had been pursuing me for a while and when he got a legal separation and moved out, we started dating. That was four years ago and our relationship isn’t what it used to be because his divorce has taken a toll on him. He has paid over $12K to his attorney and he’s got to pay the wife’s legal fees too............ Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I'm a 35 year old woman and I'm at a loss for words when it comes to my new boyfriend's four year old son. I’ve been with my boyfriend for 6 months and he felt it was time for me to meet his 4 year old son. He’s told me that I am the first woman he’s been serious about in years and he can see me as his wife someday. So, I met his four year old son and he’s a bit weird. He looked me up and down and said hello, then he stared at my breasts for a long time............ Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I got in a bad fist fight with my best buddy because of a woman that he is secretly in love with. I had a house party recently and we all had a lot to drink, so I offered to let a few people stay over. All night, my boy was trying to talk to the finest girl that was there and she was not really receptive to him. He told me that she asked about me, but she’s not my type so I didn’t pay it any mind. She ended up staying at my house because she lives in the suburbs and had been drinking............... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

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 married for 9 wonderful years and we’ve never had any major issues in our marriage. He's great with the kids, he’s a great provider and he’s a hardworking man. The only touchy subject seems to be our sex life or lack thereof. He’s 8 years older…. He’s 48 and I'm 40. He’s been taking medicine that prevents him from becoming aroused and it’s a big problem for me........... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I am a 62 year old married man and I’ve been married for 30 years. My wife and I have one daughter that is 31 years old and she still lives in our house, with her husband and their 3 children and she had the nerve to announce that she wants another child. I have told her not to bring any more kids to my house, but she thinks I’m joking. Our daughter and her family need to leave our house, or I’m going to leave our house.................. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I am a very happily married woman in my early 50s and I have an issue with my husband’s long-time friend and fraternity brother. My husband’s friend lives in another state for work, but he loves to come visit all his buddies in the city that my husband and I live in. When he comes to town, he would take turns staying at different friends’ houses. His first visit to our new home was earlier this year and he stayed the entire weekend and that was okay, as a one-time deal.......... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I am a 27 year old married woman with a two year old son that won’t stop cussing. Recently, whenever he gets frustrated or upset, he starts cussing. If he falls down and hurts himself, he cusses. If I tell him no, he cusses! I assumed he was hearing these cuss words from my husband, because I don’t cuss in front of him, so he is not hearing it from me. My husband swore to me that he has not been cussing in front of him either.......... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I am a 33-year-old woman and I recently started dating a 25-year-old man. The age difference really didn’t bother me at first but I am starting to notice that he seems to be a little bit inexperienced when it comes to sex. The first time we got together there was a lot of kissing involved so I didn’t quite notice how much noise he makes in bed. I did notice that he was talking really dirty and maybe he thinks that all women are into that or he hasn’t been with that many women.............. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, my roommate has ruined his relationship and mine. I’m in my late 20s and I have been roommates with my best friend since college. We both have steady girlfriends that are sorority sisters and we started dating them around the same time. I’m way more serious about my relationship than he is and I plan to propose to my girl soon. Marriage has not entered his mind and he still acts like he’s in college, messing with lots of other women on the side.............. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I am a young woman in my early 30s and I have been dating at 44 year old man for 10 years. We have had a great relationship until recently, when his mother moved to the city we live in. Since then, we’ve been fussing more and I’m really starting to dislike him. His true colors are showing, all because of his mother! We cannot move on with our lives because his mother is stuck on her son not being with her whenever he has extra time in his schedule............... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I’m a 33 year old entrepreneur and I need your advice because Labor Day is coming soon. I live in a nice big neighborhood and I’m friends with everyone on my block. We’re a close-knit community and each year, we have a community outing for Labor Day at the neighborhood clubhouse. Last year, I took 2 big watermelons, ice and 2 cases of soda. Since I’m a bachelor, I’m not expected to do much more than that. We send around a checklist annually so we’ll know who’s bringing what, to the party..................... 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 something single female and my boyfriend is 69 years old. When we first started dating, he was my sugar daddy and he paid my mortgage, my car note, and sent me on vacation several times a year. But it wasn’t all of the money or the gifts that got me so hooked on him… it was the sex. This man is the best I’ve ever had and he does not need any enhancements to get aroused. We’ve been together for 5 years so I was shocked when he carelessly left his phone at home recently............. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I’m a 35 year old man with 2 kids and a stepdaughter by my wife. I love my family, but I have come to a breaking point with my wife. For the second time in 4 years she has left the home and cut off all contact with me and the kids. The first time she left, she ran off with a man that she met online. She bought a bus ticket and rode out west and didn’t contact us for a month. Eventually, the guy dumped her and she reached out to me............. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.