Strawberry Letter

Dear Steve and Shirley, I’m 33 years old and single. My uncle is like a father to me and he helped my mother raise me. He is a sweetheart of a man and he loves the Lord. He’s active in his church and he will help anyone that needs him. He’s worked all of his life and he’s got a little fortune saved up. He is 58 and he has never been married, so he was anxious to settle down...........................

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Dear Steve and Shirley,  I met and older guy and I was attracted to him, but played hard to get. He begged me for a first date and I eventually agreed to go out with him. He asked to pick him up and I didn’t think much about it since his house was on the way to the restaurant. When I got to the house, he came out and so did a much older lady. He got in my car and told me that was his mom and that...

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 ad...

Dear Steve and Shirley, I’m a 41 year old entrepreneur and I own a brokerage firm. I’m dating a 40 year old former pro athlete and we met 3 years ago. He is a coach and he owns a laundromat. I have my own house and he has his house. I was driving a small sports car when I met him and he suggested I get an SUV for all of my yard signs and stuff for my business..........................................

Dear Steve and Shirley, I’m a 57 year old married woman but I’m at my wits end with my husband. He’s ex-military and wants me to do everything his way. We have been married for 22 years but since he’s retired, his full-time job is controlling me and the kids. I have always been the brains and the breadwinner of our family and I think that bothers him now that he has nothing to do daily...............

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Dear Steve and Shirley, I’ve been dating a 42 year old man for a while and his sister is one of my old acquaintances from college. I don’t use the word “friend” to describe her because she’s done a lot of shady stuff lately. She introduced me to her brother and he initiated our relationship. At first, he was dating someone else and his sister made sure I knew it. She said she loves his ex-girlfrie...

Dear Steve and Shirley,  I'm a 33 year old single female and I was dating a 35 year old man that ghosted me.  We met and it was like no one else existed in our lives.  We went on a trip two weeks after we started dating and he spoiled me and I spoiled him.  He was at my house or I was at his house every night.  He was the best lover and that deepened our connection............................ See...

Dear Steve and Shirley, I’ve been married for 23 years and my wife is very set in her ways. I listen to you all the time and I want your opinion on how to keep the spice in my marriage. Everything about my wife is old school and she doesn’t like change. We have not bought new furniture in 15 years and when I tried to redo my man cave, she got her sister’s old couch and recliner and had it in the b...

Dear Steve and Shirley,  I am a 52 year old female and I am dating a 60 year old young man.  We clicked instantly and we have been together for two months.  I may have been too forward with him after the first few dates because I wanted to rub and feel on him to see what he was working with.  I hugged him tightly one day and it felt like he was wearing a back brace.  I decided not to ask him about...

Dear Steve and Shirley, my husband and I have been married for 14 years and we’re hanging on by a thread. We have two children and sometimes I wonder if that’s why he stays with me. We never talk about our problems. Things have happened in our marriage that would make a normal couple split up, but we’re not normal. At our wedding, one of his exes showed up and cried loudly while we said our vows....

Dear Steve and Shirley, I’m married and in my mid-forties and my husband turns 40 in a month. He decided he was going to have a guys’ weekend in Mexico and then he would come back and we would celebrate together with a small group of our friends. He got his little plans together and I was watching all of the emails going back and forth........................ See omnystudio.com/listener for privac...

Dear Steve and Shirley, I’m writing for my brother because he is too upset to do it for himself. My brother is 38 and his wife is 35 and she has planned a trip for Labor Day with two girlfriends and a guy that has been her friend since they were 18 years old. This guy was married before and he has one child. Now he’s no longer dating women.................................. See omnystudio.com/liste...

Dear Steve and Shirley, you two are very fashionable, so I need your advice on how to talk to my husband. He seems to be going through a midlife crisis or something similar. We’re both 56 years old and been married since we were 30. We did get married so I could become a U.S. citizen, but we were in love. I met him when he was stationed in my country and we both had a lot of growing up to do. He w...

Dear Steve and Shirley, my husband is 76 years old and I’m 60. I worked with his daughter years ago and that’s how we met. When we started dating, he loved having a much younger woman on his arm, but as he gets older, he’s getting more paranoid and asked if I would ever leave him for a man my age. I took my wedding vows seriously and he knows I love him, but he’s on my last nerve.....................

Dear Steve and Shirley, I’m 34 years old and I own a hair salon in strip mall. I have been hanging out with a 38 year old dentist who works directly above my salon. I need your advice on how to deal with him. He is never ever pleased with anything and the first time we met, he came down to my salon and told me to turn my music down. I told him to relax and he got mad..................................

Dear Steve and Shirley, I’ve been dating a man for six years and we live with his parents in a two-bedroom house. We had to move in with them in 2020 after he lost his job. I don’t have any family in this town, so I agreed to stay there temporarily, but he just started working 4 months ago. He couldn’t find a job in his field for a long time so I was relieved when he started working full-time beca...

Dear Steve and Shirley, I’ve been in a relationship for almost two years and when I think about the things this man has shown me sexually and mentally, I am floored. He literally takes my breath away. But there are a few problems with our relationship. We’ve never spent a night together and I’ve never met his family, except for his twin daughters and their mother. It was a quick “Hi” and “Bye” whe...

Dear Steve and Shirley, I was in a relationship with a man for 6 months, but we fell in love quickly and we were living together. He is 36 and I’m 31. He was going through a divorce when we met so I made him wait until the papers were signed before we had sex. He told me that his wife divorced him because he cheated on her multiple times. He told me that he cheated, simply cause his wife had stopp...

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. W...

Dear Steve and Shirley, I’m 38 years old and I’ve been on a few dates with a 40 year old man that lives with his sister. For our first date, we met up at a miniature golf place and his sister dropped him off. He lied and said it was an Uber, but when I offered to take him home after the date, he admitted that his sister dropped him off because he knew I would see that car at his house. For our 2nd...

Dear Steve and Shirley, I’m dating a man that is so tied to his past that it won’t let him last. We are not going to make it because he’s always talking to his ex-girlfriends and his ex-wife. He has a child in his life that’s not his, but he told me that the boy will always be a part of his life. His ex-girlfriend was pregnant when they started dating and he raised the child for 3 years. Then they...

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Dear Steve and Shirley, I have been married for 22 years to a fool who thinks I’m crazy. He works 2 jobs and takes great care of me but I think he resents me because I never had children for him. At first, we agreed that we didn’t want kids, but now we’re almost 50 and he said he wants a son. Because of that, he has become very involved with a neighborhood friend’s son. I thought he was being a go...