Strawberry Letter

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Dear Steve and Shirley, I am engaged to a 63 year old man that acts a lot older than he is. His thoughts on sex and life in general shock me and I need some advice. I’m only 59 years old and I still enjoy sex and have tried to be patient with my man. He thinks I’m a freak because I try to initiate sex daily. He likes to grind and do a lot of kissing, but we rarely go all the way. I like to take ca...

Dear Steve and Shirley, I’ve been married a little over a year now and this is my second marriage. Since the wedding, my husband and I had been searching for a new church home that we mutually agreed on. We visited churches and settled at a church close to our home, with a good stern pastor. We loved his preaching style and felt really welcome there, until one Sunday when the pastor’s message was...

Dear Steve and Shirley, I need your help. I am 27 years old and I have lived with my fiancé for two years. We bought our first house together and everything was great until recently, when my fiancé’s brother moved in with us temporarily. His brother is going through a divorce and he has lived with everyone in the family. He’s worn out his welcome everywhere, so I didn’t mind him staying with us fo...

Dear Steve and Shirley, I’ve worked with a guy for over 6 years and over time, we became attracted to each other. We went out a few times and had several passionate kisses, but nothing more. He explained to me that he is in a dead-end marriage for 20 years and he lives in an apartment in the city and his wife lives in their house in the suburbs. I am divorced and my grown kids live with me. The ma...

Dear Steve and Shirley, I’ve been dealing with an older man for a year. He’s 66 years old and I’m 30 years old, so I guess you can call him my sugar daddy. I also have a boyfriend that is my age. We’ve been dating for three years and he knows about the older guy and he doesn’t mind, because I told him that he is my uncle. The older guy takes me to and from work every day because my boyfriend works...

Dear Steve and Shirley, I recently met a wonderful man and we instantly had a connection. I am a widow and his wife died earlier this year. When we met, he looked familiar to me, but I thought that it was just a coincidence. After a few dates, we talked more about his wife that had died and he told me her name. I knew his wife and when I put two-and-two together, I realized why he was so familiar...

Dear Steve and Shirley, I am a 36yr old female in a long-distance relationship with a man in his early 40s. Things are good between us, and honestly, I am ready to take things to the next level. I only have one problem and I’m hesitant to move to his hometown if he can’t fix the problem. We have been in a committed relationship for 2 years and when we are intimate, he is very gentle and loving in...

Dear Steve and Shirley, I have been married for 17 years to a man who I thought was trustworthy, honest and a good Christian man. We are both in our 40s and been together for 25 years total. For the last 4 years, he has been friends with a basic girl that he met at work. I call her basic because that’s what she is. I always have expressed how displeased I am with their friendship, but he insisted...

Dear Steve and Shirley, I have a problem that’s bugging me. My husband has always been attracted to big butts and a smile, and his girls before me were very ratchet. Recently, he’s been telling me that he is taking “odd jobs” across town for extra money. He’s a carpenter by trade and a handyman on the side. I haven’t seen any of the “extra” money, so I got suspicious. I know he likes the company o...

Dear Steve and Shirley, I’m a 52 year old woman and I need for my best friend to have an open mind. I’ve known her for most of my life and she’s divorced with a grown son. Her son was raised by her ex-husband so I have not spent a lot of time with her son. I was having dinner with my best friend and joined us for dinner to say hello. He sat with us briefly and talked about his dance studio in town...

Dear Steve and Shirley, I am in a crazy love triangle and I met my man through his wife. She was supposed to be my best friend but we always argued over stupid stuff and then finally had a big blow out and stopped talking. The entire time, our other friends tried to get us to be friends again, but nothing worked. I ran into my best friend’s husband one day and he told me that it’s best to end the...

Dear Steve and Shirley, I attend a prominent mega church and I’m very active in my church. The church threw a back-to-school bash for the children at the church and we had a pool party in our indoor pool. I volunteered to help around the pool and watch the smaller kids. Shirley, I have been losing weight for the last year and I wanted to show off my body in my swimsuit, but with a nice coverup on...

Dear Steve and Shirley, I got a divorce four years ago and I gave myself time to heal so I would not go into a new relationship with baggage. A year ago, I met a great guy and we fell for each other quickly. He paid all of my bills and he was super attentive to my needs. We went on two lavish trips and he promised me that we would travel the world together. He attended my church often and we praye...

Dear Steve and Shirley, I have a friend that can be self-centered and a bit loose when it comes to men. We’ve been friends for 13 years but I’ve never had an issue with her until recently. She likes to flirt with other women’s men and boasts that she can take any man from his woman. I just never thought it would happen to me. I started seeing a new guy and he invited me to a house party so I invit...

Dear Steve and Shirley, I am a divorced 58 year old black woman dating a 61 year old white man that I met on a dating website for black people. I thought it was strange that he was on a site that is for blacks, but I guess he likes what he likes. This man fell head over heels for me on the first date. He got up and kissed me at least four times that night, while we were at dinner. Since then, he s...

Dear Steve and Shirley, I met a man at church recently when he was visiting from out of town. He lives three hours away from me so in the beginning, we enjoyed video chatting and talking on the phone for hours. After only two months, we really like each other and want to spend all of our time together. He is ready to take our relationship to the next level and he is planning to move to the city I...

Dear Steve and Shirley, I am a 31 year old single woman and I met the man of my dreams two years ago on a dating website. He lives in Tampa and I live in Philadelphia. A few months after we met online, he came to visit me. I immediately noticed that he lied about his height. He's short. He is an inch or two shorter than me and I like tall men. I had hoped he looked a little bit better than his pic...

Dear Steve and Shirley, I am a 29 year old single guy and I have been attracted to a 27 year old beautiful woman for 4 months and I finally got the nerve to ask for her number. When I met her, I did everything in my power to sweep her off of her feet. I am a police officer and I work the night shift, so I’m home during the day. She is my mail carrier and it was an instant attraction when I saw her...

Dear Steve and Shirley, I'm a 36 year old single woman and my new next door neighbor has me concerned. She's a pretty girl in her late twenties and she was nice enough when I met her. Here’s my problem. Her bedroom window faces my bedroom window so I have to keep my blinds closed for privacy. She always keeps her window cracked and night after night, usually during the week, I can hear very loud m...

Dear Steve and Shirley, I am a 50 year old with 3 children and I have been married for 14 years. All of the children are grown and are on their own, so my husband and I have the house to ourselves. I love my alone time with my husband, but his sister is causing big problems in our marriage. His sister gets on my last nerve. She is an unstable mother and she drops her kids off at my house with no w...

Dear Steve and Shirley,  For the past five years I've been dating a man that is nine years older than me and I really love our relationship and how well he treats me. I recently started living with him and I have a problem that I need your help with. My boyfriend loves to get a big bowl of ice cream most evenings as a treat after dinner. I try not to be overbearing because he could be drinking alc...

Dear Steve and Shirley, for the past 8 years, I’ve been dating a 60 year old man and I am 14 years younger than he is. Everything in our relationship was good until 6 months ago, when he moved his 2nd ex-wife and their 20 year old child back into his home. He has been divorced 12 years, but he told me that his ex-wife is having financial problems, so he allowed her to move in. This changed our rel...

Dear Steve and Shirley. I need your advice because I really want to kick my dad's wife’s behind. I am a 42 year old single mother of two kids. My children's dads don't help me financially so my father has helped me raise my kids for the past 15 years. Well, I recently lost my job and everything went downhill. I was unable to pay my rent so I had to move out of my apartment at the beginning of this...

Dear Steve and Shirley, I have a problem with how men see me. I was married for 25 years and I got divorced three years ago and decided to move to another state for a clean slate. I’m not looking for a serious relationship right now, I want to enjoy being single a while, but I would like male companionship occasionally. So here is my problem.......... Learn more about your ad-choices at https://ww...