Strawberry Letter

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.

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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.

Dear Steve and Shirley, I’m a 32 year old divorced woman, who filed for divorce after only 2 years of marriage. Right after we said “I do,” I noticed a change in my husband and he could go 3 weeks without having sex with me. He kept making excuses to leave the house and would be gone for up to an hour when he left to “run a quick errand.” Then about 8 months ago, I walked in on him as he washed himself off in our bathroom sink, after he claimed he went to Dunkin for a cup of coffee................ 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 single female and I’ve been casually dating a man for 3 years. His wife died 6 years ago and he’s a single dad, raising a daughter. He lives in my complex and when we met, we instantly clicked and started dating. After a few months of dating, he told me he wanted to take a break so he could focus on his daughter. That was 3 years ago and I showed support by cooking for him occasionally and showing up at some of his daughter’s basketball games.............. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, for the past 10 years, I have lived with a really good female friend. Over the years, we’ve shared a bed at times and we’ve had sex when it was convenient. Other than that, it was more of a roommate type of arrangement. She dated other men and I dated other women. When we were at home, we were best friends that happen to sleep in the same bed sometimes. We never had our boyfriends/girlfriends sleep over.............. 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 and I need your advice on how to help a friend. She’s been in quarantine alone so all I’ve been hearing is how lonely she is. Well, here’s why… She looks a hot mess all of the time and being inside for 3 months has made it worse. I know everybody has been looking crazy since we are stuck inside, but she’s put on a few pounds and looks like she hasn’t combed her hair since March................... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I am 36 years old and I’ve been in a great relationship for 4 years. A year ago, I noticed a change in my man and changes in our sex life. If I initiated sex, he made up excuses like he has acid reflux and he’s scared sex might give him a heart attack. Then I saw a text on his phone that said, “I love you too.” I asked about it and he said he texted her some relationship advice and was only responding to her................... 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 woman who's been with a man for 5 years and he has had the same complaint for 5 years. He always whines about me knowing too many men. I was raised in the city we live in and my father was a prominent businessman and my family is well-known. When my boyfriend and I would go out, I'd run into guys that I grew up with, guys I worked with, went to high school or college with, etc. These are men that I’ve never dated or had sex with.................. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve And Shirley, I am a beautiful black 29 year old woman and I’m in love with a deadbeat dude but I don’t know how to get him out of my system. He’s 36 years old and we currently live with his parents. When I met him, I was the side piece for a year. I got pregnant and had nowhere to live, so he let me live in his car. His parents found out about me and they let me stay with them. Now he's divorced and our relationship is complicated. I found him at a bar with a female recently and I poured his beer on 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 48-year-old man and my wife and I have a 23 year old daughter that graduated from college and she moved back home. She asked her mom and I if one of her school mates could live in our basement for three months. I was hesitant, but my wife coerced me to let the young man stay temporarily. He was polite at first but then he started coming upstairs and trying to engage with our family................. 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 3 years. Our marriage was going good until a year ago, when he told me he was having an affair. Shortly after we met, he told me about a female friend of his that lives out of town and she’s like a little sister to him. I met her 5 years ago when she came to town for homecoming. We got along great, but I don’t trust any females around my man............... 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 late 30s and I’m dating a man that I met at church. I found out that he talked to our pastor about me and the pastor hinted that he might be ready to propose. I got excited and decided it was time to take our relationship to the next level, meaning it was time for sex. We have been together for six months and we were friends for 2 years before we started dating. We haven’t had sex, but we sleep in the same bed a lot and I like to sleep in my underwear............... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I’ve been with my husband for 6 years and we’ve been married for 2 years. I have myself to blame for what I’m going through now, because it was an issue before we got married. My husband has a problem with texting and talking to other females. When I’ve addressed the issue with him, he always says “Nothing is wrong with texting and talking, as long as I’m not crossing the line or trying to date anybody.” I believe that if one of the women he talks to or texts comes on to him, that he will take them up on the offer.............. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I feel like I already know my answer, but I want your advice anyway. My partner and I have been dating for 7 years. Yes, seven! We are both divorced and have adult children. He is 63 and I am 49. His ex-wife and I have become good friends and she has told me that he’s a good man, but a terrible husband. We live in a big beautiful home but it’s in his name only. He treats me like a queen in front of others, but behind closed doors, he’s a different man.................. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, about 6 years ago, I wrote in to get some advice about a woman I was messing with. You may not recall my letter, but I’m married and I was having an affair with a lady and it was getting out of control. I was very connected with this woman and I had started paying her bills and helping her take care of her children. The children had grown fond of me and had no idea that I was married and had another life with my wife................ Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I love my wife very much and she is the mother of my children, but I have another woman. My wife is very beautiful and smart, but she doesn’t submit to me like my mistress does. My wife wants me to be the man of the house all of the time and when I ask her for help on certain things, she huffs and puffs. I just want a partnership with her and raise our children together.................. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I am a 43-year-old woman and I have a small group of friends who have all known each other since high school. We’ve all been strict about quarantining, so we agreed to meet once a week for drinks and dinner. It’s really helped us feel better and maintain a sense of normalcy with the craziness going on in the world. About a month ago another girl we went to high school with moved back into town............... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I’m getting married soon and I need your advice. My fiancé and I met less than a year ago and we quickly fell in love. Within six months, he proposed. I called up my bestie and asked her to be my Maid of Honor. My bestie got married last year and she moved to another state. We’ve been friends since we were 5 and she was dying to meet my fiancé. Two weeks ago she came to town and I decided to throw a small dinner party and I invited everyone that’s going to be in the wedding............ 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 4 years and the sex is terrible. We dated for 2 years before we got married and we agreed to wait until our wedding night to have sex for the first time. I was focused on us having a great friendship as well as a spiritual connection, which would lead to a great sex life. He romanced me and did things to me physically that satisfied me so I just knew he was going to be a great lover................ Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dear Steve and Shirley, I am a 30 year old man and I’m 6 feet tall and I weigh 202 pounds. I work out and eat right and take care of myself. In February, I met a beautiful woman that is a few months younger than I am. She is 5’6” and she weighs 330 pounds. I like what I like, and that happens to be big girls. She is big and soft in the right places and she’s always fly and sexy................. 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 almost 2 years and I met my wife on a dating website. She was the most beautiful girl I’d ever seen and when we met in person, we quickly fell in love. I came with a little baggage and she admitted that she did too. We are in our mid-forties, so we agreed that our past was the past so that’s where we’d leave it. She works as a guest service manager at an elite country club, so I can golf at the club for free.................... Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.