Strawberry Letter

Dear Steve and Shirley, I am a 29 year old female in a confusing dating situation. We’ve been dating for almost 2 years but I waited for 4 months before we had sex, to make sure his last relationship was totally over. He has 3 kids by three different women, but the youngest child’s mother has been a problem in our relationship. My boyfriend lived with her when we met, but now he lives inside his R...

Dear Steve and Shirley, I'm a 45 year old black man. My fiancé is 56 and she’s a great woman, but I’m worried about marriage. We like to kick back and relax and drink wine and alcohol. It depends on our mood, so sometimes it’s wine and sometimes it’s the hard stuff. We pretty much drink every day after work. I’m more relaxed and mellow when I’ve had a few drinks, but she is the opposite of me. She...

Dear Steve and Shirley, I have been in a relationship for 5 years with a man that thinks we are exclusive. I’m in my late forties and my sex drive has been through the roof lately. My boyfriend is 53 and he’s a beast in the bedroom, but he’s not enough for me and he’s not as kinky as he should be. For the first time in my life, I am a cheater. I’ve been having sex with a 30 year old neighbor and i...

Dear Steve and Shirley, I’m a 38-year-old married woman and my husband and I have lived downtown in a nice condo for the past six years. We get along well with all of our neighbors but a couple months ago, a single young man moved into the condo next door to us and now we’re having a big issue with him. Since we’ve all been quarantined, our neighbor has been into porn and it’s driving my husband a...

Dear Steve and Shirley, I’ve been dating someone special for four months and so far, he is amazing. He loves the Lord and he has a great personality and a great career. When we first started dating he did not want to rush sex, so we waited a little beyond 90 days to become lovers. Since things were going so great, I took him to meet my parents. He fit in like a glove and they both told me that he...

Dear Steve and Shirley, I’ve been dating a guy for six months and he’s one of the sweetest men that I have ever met. This weekend, he disclosed some information to me and I need your opinion. He and I met when I moved out of my condo. He was the supervisor of the moving company that I used and he was very professional and handsome, so when he asked me out, I accepted. We started out as friends and...

Dear Steve and Shirley, I am the pretty young thing that wrote you about my lover that is the same age as my father. I took Shirley’s advice and asked my lover if the relationship was going anywhere or if it was just a fling. He told me that in due time our relationship would get to the next level. I didn’t like his answer, so I broke it off with him. Two days later, he sent flowers to my job and...

Dear Steve and Shirley, I’m a 27 year old single female and I’m in need of advice. I’ve had a male best friend since high school and he is an active duty officer in the military. He’s been away for nine months and he came home in April. He got married while he was stationed in Hawaii and I was excited to meet his new wife and to see him. He planned a small welcome home party in the backyard and it...

Dear Steve and Shirley, I’m ready to call off my engagement but I need your advice first. My fiancé and I are both divorced and our first marriages were terrible. I’ve been working on my issues so I can be a better wife this time. My fiancé, on the other hand, does not think he has anything to work on, but he admitted to cheating on his first wife, so he’s got some baggage. Now after 5 years of be...

Dear Steve and Shirley, I’m 22 years old and I recently graduated from college, so I’m quarantined at my parents’ house. They have been married for 37 years and the marriage has been rocky since I was a little girl, but they are still together. My father works out of the country for two months every year, so that gives my mother a break from him. In late March, I found out that my father was not o...

Dear Steve and Shirley, my husband and I are having some real marital issues right now and I blame it on Covid-19. We haven’t been stuck together for this long, without being able to go to work or to play tennis or go shopping. My husband says I irritate him all day long and I’m sick of seeing him sitting up all day watching TV. We had a big fight that got really ugly and as my husband left the ro...

Dear Steve and Shirley, my husband and I have been married for 15 years and we have 2 children. I was helping my daughter with a home school video 3 weeks ago and my husband’s phone is top of the line so I was using it. I saved the video and when I went in to edit it, I saw a lot of pictures of breasts, booties and feet in my husband’s phone. It seems that I’m married to a real creep that randomly...

Dear Steve and Shirley, I can hardly believe what I’m about to tell you and I need some advice. I have been with my girl for almost 3 years and I proposed to her. Her family lives out of state so I have not interacted with them much, but her mom comes to visit often and we get along very well. Her father is deceased and she is an only child. Since we’re getting married, we’ve been talking more abo...

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Dear Steve and Shirley, I am torn to pieces over my breakup. I was dating an old friend for two years. I am 52 and he is 45. We talked about marriage and we were in the process of buying a home. We were a picture perfect couple and then things started changing. I would see him throughout the week and on weekends, but, lately he has been busy on weekends............... Learn more about your ad-choi...

Dear Steve and Shirley, I am a 25 year old female that has been dating a 55 year old man for 2 years. He is the same age as my father and he’s very established and he takes good care of me. He has 3 children that are around my age and they don’t seem to have a problem with us dating. I don’t want to have any kids and he doesn’t want anymore, so that’s not an issue............... Learn more about y...

Dear Steve and Shirley, I hope my husband is listening today because I have a problem with him and he thinks it’s no big deal. My problem is that my husband is obsessed with an ex-girlfriend that he dated 35 years ago. She was very beautiful and popular when she was in high school and he was the star football player. When he went off to college, she married a wealthy older guy that owned several b...

Dear Steve and Shirley, I’m a 30-year-old man and my wife is 28. I was recently laid off due to the pandemic, so money has been a little tight. Because of it, my wife is making me feel like less than a man. We have a 2 year old child and she is a stay-at-home mom so I am the sole breadwinner. My wife’s attitude has been horrible for weeks so I have been avoiding her, to avoid arguing with her........

Dear Steve and Shirley, I’m a 30 year old divorced female and I’m working on my master’s degree in nursing so I wasn’t focused on dating after my divorce. But, 6 months ago, I met an amazing 25 year old man that was heaven sent! He’s tall, dark and handsome with a nice house, car, and two jobs. He is my everything and he takes good care of me. He pays bills, cooks, cleans, everything. There is jus...

Dear Steve and Shirley, I’m in love with a woman that has carried herself like a garden tool all of her life. In other words, she’s been “loose” since high school when we started dating. I dated her into my early 20s and after we broke up, I found out that she cheated multiple times. Here we are, 15 years later and she’s married now and she’s cheating on her husband with me. I have a connection wi...

Dear Steve and Shirley, I’m a 28 year old engaged female and my wedding was put on hold because of the pandemic. My fiancé and I are living together for the first time because he thought it would be fun to be quarantined together. I’m very grateful that he moved in because I’m learning a lot about him and it’s quite shocking. He is smart, a great provider and he’s got a great personality, but he i...

Dear Steve and Shirley, I have been with my boyfriend for eleven years and he’s eleven years younger than I am. When we met, I had two children from a previous marriage and he said he always wanted to have his own child with me. Well, we never got around to having children together and now I can’t have kids. I suspected that women his age would eventually get his attention, but I never expected hi...

Dear Steve and Shirley, I’m a 52 year old widower. I lost my wife 4 years ago and I’ve recently started dating again. I live in a great neighborhood and my neighbors have been very supportive while I’m adjusting to being single. I’m really cool with one of my college buddies that lives around the corner from me. He has grown kids and he and his wife own a gas station. They are essential workers so...

Dear Steve and Shirley, I’m writing for my friend because she has lost her mind and I need her to realize what she’s doing is wrong. My 28 year old friend has 2 children by her mother’s 56 year old boyfriend who I’ll call “Larry.” Her mother thinks that she has been dating a guy that she met in college and she’s never even asked to meet this guy. I honestly can’t stand “Larry” and whenever I’m aro...

Dear Steve and Shirley, I am in a relationship with a cheater and I need your advice. Last week my man was cutting the yard and he left his phone in the kitchen by mistake. It kept dinging and ringing so I checked it. His so-called female best friend texted him, “Bring me some of that Corona D.” I answered her, “When and where?” She replied, “Now. Come pick me up.” I put on a sweat suit and called...