Strawberry Letter

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.

Dear Steve and Shirley, this isn’t a typical letter about cheating. I am in my mid 30s and I’ve been single for too long. I’m a nurse and I meet a lot of great men at work, but I'm not having any luck in love. When I meet a guy, I’m optimistic and not expecting him to play games just to have sex with me. I’m the type to text right back, return calls and show up early for a date. My girlfriends say I catch feelings too quick and I’m a hopeless romantic............... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I’m a 37 year old single lady and I work with a married couple that gets on my last nerve. They’re the most happy couple in the world and they love to rub their relationship in everyone’s faces. We’ve all recently returned to the office and our boss let them share an office. They love to announce to everyone that they’re going to lunch and they walk around holding hands at all times and making flirty gestures when they’re around us................... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I am best friends with the stupidest guy in the world. He’s been dating a woman for one year and he’s ready to give her the keys to the kingdom. He’s a successful realtor and he has a nice home and 2 cars. She has access to both cars and a key to the house. Before you think I’m jealous, I am married and this is my husband best friend that’s like family to us........... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I’m married to a wonderful man that is 13 years older than I am. He is my everything and in the beginning of our marriage, we were very active and traveled a lot. Now it’s like he’s settled into being old and boring and I can barely get him to take a walk with me. I asked him if he was depressed and advised him to see a doctor. He went to the doctor and got a clean bill of health. We used to enjoy a martini in the evening to unwind and reconnect, but lately he’s turned to drinking brown liquor and I’ve noticed a change in him................. 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 because my daughter is in love with a country bumpkin. She is 24 years old and she got engaged recently and she brought her fiancé to town to meet my husband and I. As soon as they got out of the pickup truck, I thought WTH is this? He is a true country bumpkin. He has his GED because he dropped out of high school to work on his family’s farm. My daughter has a Master’s Degree and a promising career............... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I’m married to my high school sweetheart but we have only been married for 4 years. After high school, we went our separate ways and he was married for 20 years and had 3 kids with his wife. I was married for 13 years and I got a divorce and was raising my 2 children alone, when I reconnected with my high school sweetheart. We blended our families and picked right back up where we left off in high school.................... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I have been sad for a while now and I’m seeking advice on how to move past this situation. I have been in a relationship for 6 years with a married man that was loving and attentive and treated me like a priority at all times. We live about an hour away from each other and he would make a point to see me weekly and take me on business trips with him and weekend outings whenever he could................ Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I have a confession to make and I know I can count on Steve to give it to me straight. I’m a divorced female and I work as a corporate trainer. I’m 49 years old and I have one daughter and a granddaughter. Last fall, I was called to train staff at an insurance agency. One of the male trainees got my attention and asked me for a business card before I left. He left a message on my office phone and invited me to dinner the next night. I knew he was a bit younger than I am, but I was flattered and went on a date with him.................... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley. My wife had a friend that she was friends with for many years and she stopped being her friend because a non-credible person told my wife that her friend was talking about her. My wife fell out with her friend and since then, she talks bad about the friend and she gets mad if I tell her what she’s saying is not true. I learned quickly to take my wife’s side and I even added a few choice words about the old friend, so my wife would think I was on her side................ 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 single man and I’m in a bad situation. My cousin is a pilot and because he’s always out of town, he’s basically got women in every city. My cousin also has a girlfriend of 5 years and he has been talking about marrying her. She’s a successful 29 year old woman that really loves my cousin and they have a great relationship, other than the fact he cheats a lot. I’ve warned my cousin about getting sloppy with cheating and taking pictures with the women.............. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I was released from state prison a few months ago. While in prison for 23 months, I thought my girlfriend had my back and we’d get married when I came home. Boy was I wrong and I came home to a situation that was worse than prison. I was released to my own home, with my girlfriend, who has been staying in my home while I was in prison. It was supposed to be a joyous homecoming, but instead, I walked into hell........................ Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I'm 28 years old and I live with my fiancé that’s 32 years old. We have one child together and he will be the stepfather to my son from a previous relationship. I love this man with every bit of my heart and soul. He is an amazing father and an amazing man, but here's the problem. We've had issues where exes have texted his phone and I found out about it and I brought it to his attention. He still has them as Facebook friends as well.................. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, when you read my letter, I know you are going to think my boyfriend and I are young, but I am 43 and he is 48. We’ve been dating for 2 years and he is extremely intelligent. We both love the Lord and we have stable careers. So, here’s the problem. I still go out with my girlfriends and maintain a social life. Whenever I’m out, I’m not constantly checking my phone because I want to stay present with my friends.............. 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 I’m eager to meet a nice man and settle down one day. But in meantime and in-between time, I was keeping myself entertained in online chat rooms and online dating. I met a man that I paired perfectly with and his profile said he was 6’2” and athletic. His picture was nice but not really my type. We started chatting offline and would stay on the phone for hours.................... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I am a 29 year old woman and I was in a relationship with a 31 year old man. We both have degrees and promising careers. He came from a solid, middle class family and I was raised by a single mother, with very humble beginnings. We have been dating for 2 years and my boyfriend’s mother does not like me. He told me his mom had always tried to hook him up with successful women in town, but he was never interested. I tried to overlook her and I was pleasant whenever I was around her..................... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I have a 52-year-old single mother who is a loving and giving person. Three years ago, my mom kept saying she was going to reinvent herself and dress differently so she can meet a good man. My mom has always had a lot of nice men that come in and out of her life and it breaks my heart when she gets attached and the man ends up leaving her. The current man she’s dating will never leave her because he is a big loser and he needs my mom.................... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.