What to expect and the reality of it

“Dating a man in prison”

If you are a woman dating, thinking about dating, or have met a man through an online prison pen pal site who is incarcerated, you may find yourself asking one or more of the following questions:

What should I expect?

  • High phones bills
  • Dishing out money to pay for prison talk lines that enables people to accept inmate calls on their cell phones, money on his books, etc.
  • Plenty of letters from him sometimes enclosed with toilet paper made roses, drawings, other handmade crafts, and photos
  • Long distant travels for inmate visitations
  • Promises and stories of his plans when he gets released

Is it a waste of time?

Not for him. You are actually helping him pass time. You are his connection outside of the cell so you will be enlightening him by talking about all the things he is not privy to. On the other hand, you may be setting your own self up for failure because you are dealing with a man that is financially and emotionally dependent on you, and after he is released, there is no guarantee he will be with you.

Does he really love me?

If you had a relationship before, you can probably draw your own conclusion based on how he treated you prior to getting locked up. However, keep in mind that some people change based on their circumstances.  If you never had a relationship outside of prison it is really hard to tell. If you believe you are in love or he is in love, with the idea or thought of you because you have never met in person all you can do is wait it out. Remember, this is a choice you are making – to stick it out with him so if all his promises are broken and you become emotionally and financially beat, you can’t be mad at anyone but yourself.

Can I really trust what he says?

Some will definitely say all the things you want to hear because they have nothing but time. The only way to know for sure is by a person’s actions.

How will he act towards me when he gets released?

It all depends on the person. However, many women who have dated felons shared that initially he will act the same towards you because he needs you. In time, and as he adapts to the realities of society, he will become frustrated and afraid, because of the transition.  You could possibly become his mental punching bag and he will blame you for anything that goes wrong, while expecting you to do everything for him.

Protecting yourself and intimacy

Go to the local clinic to get yourself and your significant other tested for STDs before engaging in sexual activity. Regardless if you trust him or not, there are too many women being infected with HIV to take risks. If he tries to have anal sex and it is not something he did prior to being locked up, or it’s your first time with him and he makes an attempt, there is a high chance that he was engaging in homosexual acts while locked up.

Emotionally, continue to live your life productively by doing what is best for you. If you don’t, you may find yourself feeling down because of the strain he may be putting on your life. If you find yourself constantly giving him money and putting yourself in a financial bind, and emotionally drained, it is best to let him go and be by yourself to recoup. However, if you decide to stay in it, just know it will be a bigger challenge than you think.


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