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SHMS Strawberry Letter

Strawberry Letter: Should I Run Or Stick Around

Dear Steve and Shirley,

I just met a guy online who seemed cool and we just started dating. I immediately noticed that he was less educated and slightly less polished than the normal guys that I date. After our second date I could not help but notice the smell of smoke in his clothing so I asked him if he smoked and he said, yes. I was very disappointed and told him that I would never date a smoker so he stopped smoking.

My other issue with him was the fact that I noticed he had a lot of cheap black ink tattoos on his arms and neck so I asked him if he had ever been in prison and his response was, yes. I was disappointed for the second time and now he says he is getting back on his feet, going to school and trying to finally be the man that he always wanted to be. He is 44 and has never been married. I am 39 and I have not been married. I would love to settle down and have a family one day, but I do not know if this situation is right for me. I have a great job, my own place and I have never been in trouble with the law.

This guy has a 9th grade education, is working on his GED/trade school degree, lives with his mother, and only been out for two months after serving a 5 year sentence for selling drugs. I have been out on several dates with him and I enjoy his company and he treats me like a lady. I can tell he is a good person who had made some horrible mistakes but I do not know if dating him is right thing for me. Should I look for a man who is on my level? Does that man even exist? Are my standards too high? I’ve been single for three years and I know being alone is not in God’s plan. I was hoping you would read my letter and give me some insight on what I should do.

Please help.



Listen to Shirley and Steve respond to this letter below:


Strawberry Letter: My Man Seen Another Guy Picture On My Phone [AUDIO]

Strawberry Letter: Low Down Husband [EXCLUSIVE AUDIO]

Strawberry Letter Ft. Earthquake: Daughter in Love with Deadbeat Fellow [EXCLUSIVE AUDIO]

Strawberry Letter: Player For Life [EXCLUSIVE AUDIO]

Strawberry Letter: My Boyfriend Claims He’s Not in Love with His Best Friend [EXCLUSIVE AUDIO]

Strawberry Letter Ft. Earthquake: I Love Him And His Father [EXCLUSIVE AUDIO]

Strawberry Letter: Womanizing Father-In-Law [EXCLUSIVE AUDIO]

Strawberry Letter: My Father Is A Pimp [AUDIO]

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