Strawberry Letter

Dear Steve and Shirley, I’m 28 years old and single and I’ve had the worst dating history of all of my friends. I was recently dating a guy that told me he had a stalker and we had to lay low for a while until she left him alone. I understood why he might have a stalker because he is fine and sexy with a bald head and full beard. He’s 36 years old so I was intrigued by dating an older man for the...

Dear Steve and Shirley, I’m 39 years old and I’m twice divorced and back on the dating scene. When I got married the first time, I was 22 years old and I married an NFL player. We dated during high school and he promised to treat me like a princess if I ever married him. When he proposed, I got a Range Rover, a ring and the keys to a retail space and he told me I could open up any type of business...

Dear Steve and Shirley, I’m a 28 year old divorced woman and I fell on hard times during the pandemic. I got laid off and then I got a bad case of Covid and had to move in with my father and step-mom. That’s where I met my step-mom’s 69 year old brother and he swept me off my feet. We started working out together and we ran a marathon together. He started out giving me money for my hair and nails...

Dear Steve and Shirley, I would never write into your show but I’m in need of help. I’m a 32 year old single man and I have a female best friend. We had been in a plutonic relationship for 8 years and we messed all of that up after we started living together. It got too convenient and although she’s a little overweight, she’s still a very sexy woman and she knows how to please me. It’s been a frie...

Dear Steve and Shirley, I’m a 57 year old single woman but I am dealing with a man that is slightly older than me. He’s a nice man and he just lost his wife so he’s trying to settle down with me. We have great chemistry in the bedroom and that is what’s the most important to me. He matches my freakiness and has taken it to a whole new level but after five months of dating, he said he wants to only...

Dear Steve and Shirley, I have been dating a man for almost two years and I won’t move in with him until I get a ring and he’s fully over his ex. He was in a 10 year relationship when we met and he said that he was just looking for a reason to leave. He said that he didn’t love her and would never marry her because she has anger issues and she started smoking cigarettes...............................

Dear Steve and Shirley, I’m a 47 year old single man and I moved to Atlantic City recently and I share a home with my elderly uncle. He has always been like a father to me, so what’s his is mine and vice versa. He has always had the flashy cars and nice suits and he still wears a huge diamond pinky ring. His wife died a year ago so he’s adjusting to the single life since he’s a young 72 years old....

Dear Steve and Shirley, my wife and I have been married for 22 years but for the past 4 years, we’ve lived apart. We talked about divorce but we never did it. It’s very weird but we fell into a pattern of co-parenting and just never filed for divorce. Every holiday, she invites me over so our family can be together. Every Christmas, I sleep in the guest room and wake up, cook breakfast and then we...

Dear Steve and Shirley, I’ve been divorced for almost 3 years and I moved away after the divorce to start anew. My husband was an avid cheater and my mother finally told me after he’d been having an affair with a woman for over 6 months. My mother is employed by my ex-husband as his accountant. He has two businesses that do very well in the small town they’re in................................. Le...

Dear Steve and Shirley, I’m 35 and my husband is 42 years old. I met him at a gas station 3 years ago and he had a cast on his leg and he was trying to pump gas. I saw he was struggling, so I went to assist him. We stood and talked for a few minutes and then he asked me out. The rest is history. We moved in together a year or so later and that’s when I realized that I fell in love with a soft man...

Dear Steve and Shirley, I was dating Mr. Right for almost one year and we got a condo together and looked at rings together. He is a physician and his practice is about an hour from where our condo is. We dated publicly and I met all his friends and his sister. He never gave me any reason to suspect that he was married. He is an avid golfer in his spare time and he usually stays at the resort wher...

Dear Steve and Shirley, I’m 46 and I’m dating a man that’s 47 and we met through mutual friends. We’ve been together for 2 months but I feel like you don’t really know a guy until stay overnight with him. We decided it was time for sex and he was very excited and said he would get us a room at this historic inn with a rooftop bar. I was so ready for this night because this man is fine…...............

Dear Steve and Shirley my husband and I’ve been married for two years and when I met him, he came from out of nowhere. I do not know anyone that knows him and could vouch for his character. I knew he’d been married before and I found who she was and how she looked and carried herself. On social media, she was dressed ghetto and she loved multi-colored wigs but she’s a nurse so she must be professi...

Dear Steve and Shirley, my husband and I have been together for a total of 15 years. I’m 34 and he’s 42 and we have 1 child. He’s a police detective and he’s fairly short for a man, but women do not care as long as he’s in uniform. He’s got that Napoleon complex going so he acts like a badass and a know-it-all around our family and friends. When it comes to him cheating, he’s been caught in multip...

Dear Steve and Shirley, I’m 51 year old married woman and I’ve been with my husband for 7 years. We met at a rap concert while picking up our daughters who were both 16 at the time. He and I started talking about how we shouldn’t have let our daughters go unchaperoned. My daughter and her friends came out first and he got my number before I walked away. We instantly clicked and he proposed after a...

Dear Steve and Shirley, I’ve been with my man for about 5 years and he is a nice, kind hearted, Christian gentleman. We met at a work convention and he told me that he was divorced. That is all we have in common. It took me a few years to notice how he’s clingy and soft. I hate to call a man weak but he has no backbone when it comes to putting someone in their place, including me................ L...

Dear Steve and Shirley, I’m a board-certified registered nurse and I was raised in public housing by my aunt because my mother had me when she was 16. After I graduated from high school, I found out my aunt was sleeping with my boyfriend so I beat her up and spent time in juvenile detention. From that point on, I was told that I wouldn’t amount to anything. I beat the odds and I got a nursing degr...

Dear Steve and Shirley, I am married to a man that was my King and he messed it all up by having a female best friend. He didn’t have a physical affair with her, but he had an emotional one and he shared intimate details of our marriage, good and bad. Then he encouraged her to call me and have a talk with me about how unhappy he is in our marriage. When she called, I got so tee’d off that I invite...

Dear Steve and Shirley, I have been married for 2 years to a man that is 24 years older than I am. I was his side piece for the last 2 years of his marriage and he got divorced to be with me. After we got married, things changed. I had to accept that my husband was not going to be monogamous, partly because he was having sex with me while he was married. I never signed up or agreed to an open marr...

Dear Steve and Shirley, my wife and I have been together for four years and married for almost a year. I was planning to propose to her but she got pregnant and sped up the process. I’m 52 and she is 40 and is head over heels in love with our newborn. The baby is all she cares about. I overheard her telling her mother that she got exactly what she wanted, a man to take care of her and a son that l...

Dear Steve and Shirley, I’ve been dating a very attractive woman with the perfect body and beautiful brown skin. I met her at a gym and she asked me out, which I loved because she is not afraid to go after something if she wants it. We have been dating for a little over a month and we finally had sex over the Labor Day holiday. I wasn’t expecting the performance I got.................................

Dear Steve and Shirley, I’ve been with my boyfriend for 5 years. He’s 30 years old and I’m 28. Since the pandemic hit, he’s been drinking a lot. At first it was out of boredom to pass the time and I didn’t mind it because it was just beer. Now he’s drinking at least 30 beers a week and our recycling bin stays full of beer cans each week. He’s swapped out his coffee and bagel for a beer before he h...

Dear Steve and Shirley, my husband and I have been together for almost 20 years. When we first started dating there was a female “friend” that was in his circle of friends. I didn’t think anything of it for a while but there were red flags that kept popping up and there was a certain vibe that I kept picking up on whenever they were in the same space............... Learn more about your ad-choices...

Dear Steve and Shirley, I’m a flight attendant and my schedule is very demanding because I do international flights. I’m in town for a few days and I’m gone for a few days. My boyfriend hates that his goodies aren’t there for him daily. He calls it goodies and you call it the cookie. Anyway, I need him to realize that there’s more to life than his goodies. He hates the word NO so when I am not in...

Dear Steve and Shirley, I have been married for 7 years to a man that is wonderful in every way, except one. He doesn’t respect my time or my privacy. I knew him for many years prior to dating him and we would meet as friends for dinner and drinks when he was in-between relationships. He went from relationship to relationship before we started dating because he is the type of man that does not eve...