Dating Someone Who Just Got Out of Jail – Pros, Cons & Things You Must Know

by John Santana

Dating a convicted felon can be challenging in many ways. There will be a stigma tied to your partner that will follow them, and you, wherever you go. It can be hard to keep something like that under wraps, so you will likely experience judgment and limitations in different walks of life.

Dating a convicted felon is a real roller coaster ride that can cause a strain on the relationship. The ups and downs can be exciting at times, but there are real concerns to consider. You just need to know what to expect first.

Find out everything you need to know about dating a convicted felon to see if it is worth the negatives and figure out how it can work for you.

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Dating A Convicted Felon: Pros

1. Felons are people too

  • A convicted felon can still be a nice person

Let’s not deny it, there’s a reason you are considering dating a felon. A felon can still be fun, funny, interesting or unique, even though they committed a crime.

They may have broken the law at a difficult time in their life, they may have had understandable reasons, they may now be a changed person. They may still deserve a second chance. And hey, some people love an exciting love story. The love forbidden and frowned upon by society has its charm.

2. They are More Understanding Of Life

  • They have seen the worst of humanity and can be more lenient on things

When life throws you in jail for a felony, you tend to learn a lot and have time to absorb different life theories. They are likely to be more mature than you in the way they think and act.

Their mistakes cost their freedom. They might be very good at controlling themselves right now to avoid that life again. Most people find their convicted felon lover more gentle and easy-going. Once you have seen the worst in humanity, nothing else matters anymore.

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3. They Can Handle Bad Situations

  • They are resilient in different situations

Some people can only go through the highs with you, but not the lows because they don’t know how to handle it themselves. Those people will only drag you down together. This does not apply to a convicted felon.

She is stronger than anyone else you have met. Bad situations are only another opportunity for them. You will find comfort in dating a convicted felon and be impressed by the way they handle challenges. It is a wonderful chance for both of you to grow together as a couple.

Dating A Convicted Felon: Cons

1. They Might Do It Again

  • Convicted felons are more likely to commit the same crimes

Although it is not always true, it is more likely for a convicted felon to commit the same crimes again than a regular person committing a crime. They did it before and maybe they feel disgruntled that they got caught. Committing the same crime could be a way to escape.

You can be there for them but if they do it again, they will get put in jail for a longer time. The constant worry can be overwhelming. And it can be hard to build trust in the relationship.

2. The Stigma Makes It Hard Financially

  • You are likely the financial pillar of the household

The unjust stigma circling convicted felons makes it hard for them to get a job. Therefore, most of them struggle financially. If you are dating one, be prepared to pay for most of the expenses incurred on your dates.

3. Housing And Social Benefits Are Difficult

  • Your future together comes with a lot of challenges

Ex-cons are denied public housing and plenty of other government benefits. They cannot apply for many things or vote. The dating part might be fun.

But when things get serious, you will see the tough reality of working out a future together because it seems like every aspect of society rejects a convicted felon.

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Common Scams To Avoid When Dating An Ex-Convict

When you choose to get into a dangerous game, you have to take the risk. Dating an ex-felon is not always rainbows and unicorns.


There are many people out there using this as a trick to scam others. Before you get hooked on the special one, here are a few main things to steer clear of.

Financial using

What are they asking from you? It can be a real soul connection but be sure to read the signs when someone is using you for money.

Perhaps they are making a lot of excuses about needing the money and your signature for some documents. You can feel that they are not interested in you as a date. They are scamming you for money.

Emotional using

They are not after your finances but your emotional needs. A felon has been through a lot and may be looking for someone as an emotional crutch.

They may have needed to use emotional manipulation in the past, so they are really good at it. Think about whether it seems like they are with you for the right reasons? It is easy to feel extremely attached to someone in need.


Are they a real convicted felon or just someone pretending to be one to grab your attention? It is easy to tell when someone is just acting.

When you ask more questions about their life, you will start to see the little details that don’t add up. A lot of people pretend to be ex-cons to catfish others for attention.

Dating a convicted felon does not have to be very complicated. You just still need to exercise your common sense to protect yourself from scams like any relationship.

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Meeting A Convicted Felon

You might find you meet a convicted felon by chance in a park or bar— just like anyone else. Although understandably, it is not something people advertise when chit-chatting. Dating for convicted felons is difficult in real life. However, there are certain dating sites that are open to all.

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If you are looking for an understanding relationship that is non-judgemental of convicted felons try some of these sites below.

You can also expand your network to people going through a similar thing if you are already dating one.

Bang Locals is an adult dating site that allows you to seek any types of relationship you want, including the taboo ones. No one will judge your preferences. All your secrets are safe here.

You will find members looking for all sorts of matches in their profiles, including ones that would be deemed weird in society. But that’s the best part about it. Nothing is weird on this platform.

All your wishes are respected and will be reciprocated. You can put in keyword searches and write in the description who you are looking for and what excites you. It has been successfully matching people from all over the country.

Adult FriendFinder is another great option because of its large user base, with over 55 million registered users from around the world. This community-like dating site has a forum where members can start discussions on any topic.

Members are always helpful in providing resources even if they are not a good fit themselves. The more extensive your network is, the more you will know about dating ex-criminals and what it is like. You will hear all kinds of stories that will blow your mind.

Finally, Ashley Madison, possibly the queen of taboo dating sites. At first, the trending site got panned for promoting adultery. The site is so much more than that. It is not about breaking relationships but about finding yourself. Everyone is accepted here. There is no sexual preference too “taboo”.

It can draw ex-felons to sign up because of its superb security system. Information leak is almost impossible. Therefore, it is one of the safest dating platforms for those who wish to keep everything private.

No one can hack your account and track you down with the information you provide on many dating apps. Many with a criminal record often do not feel secure when going online. They are worried that their past will catch up with them. Most dating sites do not cater to the needs of this specific group but Ashley Madison has done it.

Final Thoughts

Being with a convicted felon is full of challenges and there is no way to sugarcoat it. But once you sail through, it can be the most comfortable and loving relationship ever.

No one knows how a relationship will go until you try. If it has been a fantasy of yours for a long time, the only way to see how it feels is to experience it.

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John Santana

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