You’ve probably heard people talk about the “baggage” we all carry in our lives. It might be the baggage that came from a lousy childhood, a bad marriage, an unhealthy friendship, and so on. The simple fact is that everyone you meet is carrying baggage, and as someone who spent time in prison, that sentence is now part of your baggage.

Baggage is a fact of life, and everyone has it, but there are some types of baggage that have to be discussed more often than others. This is especially true for those of us who have done prison time and who are now starting to date. After all, if we go out with someone, like them, and see them again, it is likely that you’ll have to let them know all about yourself, and that time in prison is a part of who you are. It’s pretty daunting to think about telling someone you’ve been behind bars, but here are some simple “dos and don’ts” to help you out:

  • Honesty is essential – It is important that you are always honest about your past, but that does not mean that you must spill your guts on the first date. No one ever reveals their “baggage” on the first date because it would not allow the other person to get to know you. After all, a lot of people have some set ideas of what it means if someone went to prison, and that might stop them from getting to actually know you. So, don’t put it all out there on the first date, or even the second. (Pavlo, 2010)


  • Use “simmering” – If you’ve gone out with someone a few times, and you really like them, it is time to create a “simmer”. Do this by saying you “had some challenging times” a year or two or a few months earlier. Then tell them that you’ll share this “heavier” stuff with them after your fourth or fifth date. If things keep going well, and you hit that date, then you can let them know the whole story.


  • Don’t forget you are a human being, too – Be careful about being too hard on yourself about your past. After serving a prison sentence you might feel very insecure and think that no one will want to be with you after that. This is totally untrue. You are human. You made mistakes. You paid the price, and now it’s time to move on. You are honest and not hiding the truth, so it proves you are being fair and open, but there is more to you than that prison sentence. So, don’t let it stop you from dating, and don’t make it an issue that forces you to accept anyone who is “willing” to accept you. You deserve everything that everyone else deserves because you are human, too.

Dating after prison can be tough and scary, but when the right person comes along, they will see you and look past anything from your past.



Works Cited

Pavlo, Walter. Dating After Prison. Forbes. 2010.

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