Strawberry Letter

Dear Steve and Shirley, I am a 48 year old single, educated and professional woman that has never been married. I have dated 3 guys in the last 8 years and decided to give it a rest until recently when I met a very nice man that works with my aunt. We talked a few weeks over the phone before we met. Then he called me one day and said he’d been in a bad car accident and his face hit his steering wh...

Dear Steve and Shirley, My boyfriend and I have been dating for about 5 months and he’s the best man I’ve ever been with and he treats me really good. There’s a situation that I’m dealing with and my man doesn’t understand why it’s bothering me. When we first met, he had just gotten a divorce. I mean it was literally finalized the day before I met him. Because it was a quick divorce, he was still...

Dear Steve and Shirley, I’ve been married for 8 years and my wife has owned a trendy clothing boutique for 4 years. She decided to hire young, attractive females to represent the type of clothes she sells. The store manager is a gorgeous 28 year old woman with a banging body. Two years ago, my wife decided to help her pay for body contouring procedures so she can always look great in the clothes a...

Dear Steve and Shirley, I really hope you can help. I am 41 and my husband is 43 years old. We’ve been together for a total of 13 years and married for 10. Throughout our relationship there have been situations where my husband was getting attention from lots of different women and entertaining them on the side. This was all before social media got amped up. I would notice him buying new clothes o...

Dear Steve and Shirley, about 2 years ago I messed around with my sister’s husband after a drunken night out. I made him swear that nothing would ever happen between us again. We managed to stay away from each other but he would text me often, begging for just one more night with me. He would tell me how sexy I am and I’m the best he’s ever had and he’s with the wrong sister and all of that..........

Dear Steve and Shirley, I have a problem and I've been praying over it for years but I can’t seem to get over it. I married a man when I was 26 years old and he was 41 years old. We had a great married life, a nice big home and three lovely children. I thought our fairytale would never end, but it did. We were married for 8 years and on his birthday, he asked me for a divorce and served me papers....

Dear Steve and Shirley, I have a loving heart and always try to help others. That being said the other day I was in the discount store buying toiletries to make packets for the homeless. I keep at least five packets in my car at all times and I give them out when I see the need. So I was in the checkout line and there was a couple in front of me. I overheard the lady ask the clerk how much was tax...

Dear Steve and Shirley, I am a 47 year old divorced female and I am in need of advice. I am in management at my company and I own two properties and a boat. I have two nice cars and I am very active in my community with charities and civic organizations. After I got a divorce I vowed to live my life on my own terms and treat men as an option not a necessity......................... Learn more abou...

Dear Steve and Shirley, I've been dating a great man for almost 2 years and before the pandemic, I moved in with him. He had high hopes of having sex more frequently but just the opposite of that happened. I’m 28 years old and he’s the only man that I have had sex with in my life. I agreed to move in with him because we’re at each other’s house every night anyway but I do want to marry this man, s...

Dear Steve and Shirley, I'm a 34 year old woman and I'm married. I found the man of my dreams and he’s treated me like a queen since the beginning of our courtship. We’ve been married almost a year and until recently, my life and marriage were great. He’s in his late 40s and he’s having issues with high blood pressure so his doctor put him on a high dose of medication. Because of all of the medici...

Dear Steve and Shirley, my ex-husband and I are both in our 40s and we have three children under age 12. We divorced over two years ago and recently he allowed his girlfriend to move into my old house with him. The kids mentioned it, so I asked my ex to let me meet the woman that my kids are around. He got upset and said it’s none of my business. I said I should know who’s around my children and h...

Dear Steve and Shirley, I am having a major problem. My fiancé and I have been together for almost 2 years. She is 37 and I am 29. In the early stages, we use to throw down in the bedroom! I'm talking about doing it everywhere like 5 times a week and multiple sessions at a time, to the point where we ended up with bruises or bite marks. Her hair could never stay done back then. But lately, I can b...

Dear Steve and Shirley, I'm a 28 year old woman and I recently got engaged to a man who's almost perfect. We're on the come up and have promising careers and our life plans are laid out. We want the same things, but there's one issue: He hates my mother. I admit she was a little tough on him when they first met, but she only had my best interests at heart. She asked him a lot about his background...

Dear Steve and Shirley, I am a 29 year old single female and I am in love with a man that I can’t have. We started out as friends ten years ago and one thing led to another and we made love. I must have the magic touch because he was stuck like glue to me after that. I moved to another city and before I left, he asked if I would be his girlfriend. He came to visit me every weekend so I never in a...

Dear Steve and Shirley, I am a 50 year old married man and my wife and I have been married for 11 years. When we got married, I was working on my doctorated degree and I worked full time and struggled to take care of her and our newborn child. She decided to start school herself after having our second child. She got her master’s degree in 2019 and I expected her to apply for a job but instead, sh...

Dear Steve and Shirley, I am 34 years old and I’ve been dating a sexy, chocolate man for four years. We have a very active sex life and during the lockdown we started spicing things up and filming our exploits around the house. He’s very kinky and likes it when I dominate him and tie him up. We have a three year old son and because of the lockdown, my mother hasn’t been able to see him for almost...

Dear Steve and Shirley, I am 34 years old and I was dating a guy that’s 32 years old and we broke up because he said I am not a team player. A week ago, he had to put his car in the shop and he asked if I could pick him up from the repair shop. I went by to get him and he said his car would be ready in a week. I had planned to drop him off at home and go to dinner with my co-worker. I got to his h...

Dear Steve and Shirley, I’m a 33 year old married woman and my husband and I had our first child 6 months ago. My husband is a musician and he’s back to traveling a lot, so he suggested that we hire a nanny. I welcomed the help and when my son was 2 weeks old, we hired a 26 year old girl that had just moved to the US from Belize. She is beautiful inside and out and she has a big family so she’s be...

Dear Steve and Shirley, I’m a 51 year old man and I have a wife but I haven’t lived with her in 4 years. It’s a long story but I’ll try to make it brief. Four years ago, my cousin had a bad divorce and he needed somewhere to stay, so my wife and I let him rent one side of a duplex we own. I made him promise to be respectful to my older tenant that shared the duplex with him because she’s a Christi...

Dear Steve and Shirley, I’m a 36 year old male and I misjudged my fiancé. I met her on social media and we had a long-distance relationship for five months. When I first visited her, I should have known better than to pursue her. She’s 32 years old and lives with her mom, her 3 children, her 2 sisters and 2 nieces. But she was always well put-together and she had her own tax business, so I gave it...

Dear Steve and Shirley, I was a late bloomer and did not have a lot of dating experience until I was in my early twenties when I got braces and lost a little weight. Men loved it and would take advantage of me. I thought I had life figured out by the time I was twenty eight years old and I met the man I wanted to spend the rest of my life with.................. Learn more about your ad-choices at...

Dear Steve and Shirley, In 2017 I met a handsome man at a nail salon. He stared at me the entire time so I gave him my card as I left. He called and invited me to his apartment for dinner and we have been together since that night. He’s a big flirt and a bit too outgoing and it’s always bothered me. Two years ago, I started checking his phone and he was always talking to different women. Whenever...

Dear Steve and Shirley, I’m a 27 year old single man and I would love to stop sneaking around with the love of my life. I have been friends with my secret lover for 20 years and our parents are best friends. Our families did everything together for over 20 years but they had no idea about our secret romance. She and I have been best friends since we were 7. By the time we turned 13, she was blosso...

Dear Steve and Shirley, I’m a 38 year old single mother and I’m in a crazy situation with my exes. I was married eight years to a man that cheated on me multiple times. The first time was right after I’d had our first child. I forgave him and we moved on with life. Three years later, I got pregnant again and he started acting out again. I was in labor when I found out he cheated the second time. H...

Dear Steve and Shirley, I am a single mother of two children and I had my first child when I was 16 years old. My oldest daughter is 28 years old now and my youngest is 26. As my daughters grew up, I had a lot of different men around them before I settled down with a man that was in prison. I made lots of bad choices and did things I regret, all for this man. When he was released from jail, I let...