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How Do You Successfully Date a Prisoner?

— January 19, 2021

When dating a prisoner, love isn’t everything.

Dating in the free world is difficult enough without the struggles of living confined in prison. When it comes to dating a prisoner, love isn’t everything. Should you choose to do it, how would you date a prisoner? We have collected these helpful tips. 

Get the Mystery Out of the Way

Both of you should use the talking stage to discuss important matters. Become acquainted with the prisoner behind the jumpsuit, and let them know you too. Talk about your interests and ask about their plans for when they get out. This stage would be an ideal opportunity to measure how well you two could match if you date.

Money Matters If You’re to Date a Prisoner 

If they lose interest, they only liked you for finances. Explain to them that you won’t spend any cash on them aside from regular calls and when you come by to see them. This significant boundary is vital if you are trying to date a prisoner. Wait a little while before showing them that you can finance the date. If they lose interest, then you’ll be able to tell if the prisoner only liked you for finances and not an actual date.

Maintain Realistic Expectations

Are you searching for love or somebody to date and start a life with? Do you realize it will be extra challenging for them to find a new line of work? 

If you want to date a prisoner, let them know your expectations for them and let them tell you about theirs.

Time Works Differently for Prisoners

Even though the prisoner has more time than they could spend, just a small amount of that gets to be spent on dates with you. Instead, you could focus on trading letters and talking over the phone, and that would still be too little time to spend with the person you are to date.

So, suppose you are the sort of person who sets relationship achievements depending on how long you’ve been dating. Then, you should reexamine that and focus more on the beauty of time spent together on dates.

Dating Sites

Most online dating sites don’t support violating the law, but they can provide a safe place for prisoners who have paid or are serving their sentence and permit prisoners to restart their dating life and meet people who won’t pass judgment on them. It also allows people on the outside to date a prisoner online and experience love.

Sexual Compatibility: Test the love connection

Man and woman kissing; image by Juliette F, via
Man and woman kissing; image by Juliette F, via

How do you date a prisoner when no conjugal visits are permitted? Call or send a sexy suggestive letter to the prisoner you want to date. It’s also an excellent way to observe what different issues might be waiting for you in the future. During talks, are they quieter than you’d like? Do they have sexual addictions?

All of the information you collect is a way to better know your future partner. Communication is the best way to test a love connection with the prisoner you want to date.


Hopefully, these tips help as you date. One advantage of stretching out your dating alternatives to prisoners is that you’ll get an open mind for relationships. Love can be found anywhere, and with the right approach, it can prosper. Just remember that you’re meeting prisoners, so play it safe and ensure you’re not placing yourself in a dangerous situation as you put yourself out there.

Tell us how you met your prisoner date and how you’re making it work.

Join the conversation!