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Guy has criminal background. When do you let the past be the past?

Tagged as: Big Questions, Dating<< Previous question   Next question >>
Question - (24 August 2021) 10 Answers - (Newest, 29 August 2021)
A female United States age 30-35, anonymous writes:

Over the course of a year, I have fallen in love with a man who occassionally comes to service my work place’s building.

He has also developed feelings for me which we both recently admitted to.

The characteristics he has exhibited so far in my observation of him over the past year are:

-Kind hearted

-Giving

-Always willing to give a helping hand to anyone without expecting anything in return

-Showed me he values integrity — turning in money he found in the workplace. Said if he finds 10 cents on the ground, he doesn’t touch it.

-Says his boss trusts him immensely. After 5 years working for his boss, the boss has gotten to a point where he trusts his honesty and intrgrity so much, he no longer asks him for reciepts of materials anymore, yet he still provides them no matter what

-Good father to his children—even heard how his daughters, mother and sister speak to him. They adore him

- Reliable and prompt to his job

-Highly respected by his boss and colleagues —so much so they begged him to not quit

-Hard working man with his own business and side maintenance job—in some ways even a workaholic

-Transparent in how he's thinking/ feeling. He’s even admitted things to me any person would be too scared to share

-Told me back when he was a mechanic, some people have gave him the run around in paying him, but that the hurtful part for him was not the money but the lack of integrity and dishonesty

, I fell for him because of the integrity factor and ALL these things I learned about him. I really did.

However, recently when getting to know him more, he shared that from highschool till the age of 30, he had been selling mostly pot and some coke. He’s 50 now.

Said he stopped doing it for the wellbeing of his young daughters and all the lives he had affected. He didn’t elaborate too much on the affecting other peoples lives part. Not sure if from guilt.

I know this was 20 years ago and I wouldn't want someone to hold MY past against ME, but how do I know when I should let the past be the past when getting to know someone I am heartbroken hearing this because I don’t know if I love him anymore

View related questions: heartbroken, money, workplace

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A reader, anonymous, writes (29 August 2021):

Truth is, he has committed crimes that he has yet to pay for. If you feel you can live with that. Fine!

That's my final opinion.

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A reader, anonymous, writes (28 August 2021):

This is verified as being by the original poster of the question

Thank you everyone for taking the time to answer my question and offer your knowledge and points!! Have a wonderful day!

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A female reader, Tinacandida United Kingdom +, writes (27 August 2021):

Tinacandida agony auntGive him a chance. Everyone deserves a second chance. We all have to grow up some time and act more responsibly.

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A reader, anonymous, writes (26 August 2021):

If he has never served time, that's a whole different situation!

He could be implicated or somehow linked to a criminal investigation, which might bring-up his name. You made it seem the guy was a former convict. His past could catch-up with him anytime, it doesn't matter that he isn't doing it now. If someone died of an overdose, or there are ties to a former drug ring; he could still be implicated and have to serve time. There could be an ongoing case, it it's just a matter of time. He may claim it to be a long-time ago, but you don't know that for sure.

I totally misunderstood your post. He could have left-out a lot of details; and may not be giving you an accurate timeline about when he was involved, for obvious reasons. He likes you.

Like Honeypie, I'd take a pass. His past could catch up with him any day!

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A female reader, Honeypie United States + , writes (26 August 2021):

Honeypie agony auntI have to agree with Carrie,

There is WAY too much bragging about himself for my taste. Like someone seriously padding their "resume" to look like they are better than they are. He is basically saying that his boss trusted him SOOOO much and YOU should too.

You have to decide if you want to date him or not, mainly based on HOW he is as a person - not what he TELLS you.

Does his actions match his words?

Would his criminal past affect YOUR future? As in, can he get a passport, buy a house?

Honey, he is also almost twice your age. He is 50. Are you really looking for a partner that old? And let's not forget... He has had 20 years to "perfect" his lies.

He was OLD enough to know what he did was criminal. And he still continued for over a decade to sell drugs. I think that says something about a person. Does it mean he can never change? No, people do change. Others just get VERY good at hiding the dark stuff.

If you have a GUT feeling that this is NOT really something you want to deal with in a partner - THAT is OK!! You need to trust your feelings too. Especially when it comes to intimate partners.

For me, he would be a hard pass. NOT so much (but partly) because he sold dope in his past for 10+ years, but the bragging? That has me thinking that he is WAY overcompensating for something here.

And yes we ALL judge people. It's a survival skill. Sometimes we judge too harshly (without doubt) YOUR priority is finding a partner whom you can trust. You are not sure this guy is that someone. And that is OK.

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A reader, anonymous, writes (26 August 2021):

With me that would be a deal breaker, so would being in debt, not being able to earn good money in a legal and normal way etc. Usually when people resort to earning in an illegal and iffy way it is because they lack a real education and skills they can use to earn well. But if you are in the same boat as him, where you are also not skilled or having a good income in a legal way then you are birds of a feather, and you are well suited. You have no right to expect him to be able to offer you more than you offer him. It's when people would be asking you to down date and date lesser people than you could easily date otherwise that it is wrong.

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A reader, anonymous, writes (25 August 2021):

This is verified as being by the original poster of the question

Thank you WiseOwl for your helpful response. To clarify, he has not served time, he just had told me about his past doings. Thank you deeply from the bottom of my heart

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A reader, anonymous, writes (25 August 2021):

The Pharisees mocked and scoffed at Jesus Christ for mingling with debt collectors, scoundrels, and sinners; because God knows that we can all be reformed and repentant. Those who repent of their wrongdoings deserve forgiveness and a second-chance. That's not my opinion, it's what the Holy Bible is all about.

The purpose of prison is supposed to include rehabilitation. It's not just where we warehouse human beings we throw-away. There are hardened, disreputable human beings who would cut your throat, if you look at them the wrong-way; but there are people who've made bad-choices, were in the wrong place at the wrong time, with the wrong people. The punishment should fit the crime. We know our justice system is in need of reform. Seems if you're rich enough, you can literally getaway with murder! A criminal-background doesn't have to scar and stigmatize you for life.

You still owe a debt to society and you must pay the consequences of your actions, if you are convicted of a crime. Yet, God forgives all people, for whatever we've done. There is a catch. You must be repentant and seek redemption by changing your life. It's best done by giving your life to Christ; but it starts with wanting to live a productive life, and caring for others. Just as you have described the gentlemen you're falling for.

Many of those who have gone through the penal-system are repeat offenders; and their criminal-behavior is pretty much their chosen lifestyle. They won't change, they just make it their objective to do what they do, and not get caught. They'll lie, cheat, steal, and live in the shadows; and those are the kind of people you should best avoid. You can't be the naive-type and deal with people with this kind of past. You need self-confidence, strong character, and a God-given sense of good judgement and discernment. Gullibility and vulnerability are the weaknesses that are targeted by bad-people who will use and abuse you. Some people are very good at hiding their true selves. To some degree, this is true in all of us! We hide what we're ashamed of, and we try to project and display only the best things we have to offer.

You've obviously given him a good personality evaluation and personal-shakedown; to get to know his origins, the people in his life, and how he has repaid his debt to society. He has in-turn, been forthcoming and transparent about who he was, and who he is now. That's good!

He sounds like a man of solid character, and sound judgement. He has a work-ethic, and he is beloved by his mother and children. I'd say he sounds like a good-catch; as long as he doesn't relapse and return to his old ways. Never enter any relationship, no matter who he is, with the notion you're going to change anyone. We often make the mistake of believing our love has some magical-influence over bad-behavior. It doesn't. Keep both feet planted firmly on the ground.

If you are a woman of faith, and you believe in God. If you've given your life to Christ, as a Christian; I'd say his life becomes full-circle, once he gives his life to the Lord. We need God's temperance, grace, and guidance to keep us on the right path. That's what keeps him on the right-track. Of course, this only applies if you yourself are a believer, and you abide as a Christian in faith. If you belong to any spiritual-faith or belief; once you're both on even-standing spiritually, you're equally yoked.

It's always a case by case basis. You have to see a long history of productive living to prove anyone has changed. You can be pretty evil; and never have once set-foot in a courtroom, let alone gone to jail. Case in point, take a look at the unethical-people running our country! Many are vile, greedy, and corrupt; so we can't always judge those so harshly who had to do time. Many who belong in jail have evaded justice!

If any man or woman has served their time with good-behavior; and they come-out wanting to work, return to their families, and society. They deserve jobs, respect as citizens, and a right to vote. The point is to return to society as rehabilitated-citizens; but they will carry the stigma of being a convict, because the evidence and the crime they committed also defined the person they once were. In almost all cases, they had a choice.

Be blessed, and use good discernment. If you are indeed a woman of faith; pray, and seek God's opinion, and He will guide you. I think he sounds great; but only Jesus knows our hearts.

It is up to you to make the decision to let the past be the past; because it is you who will have to live with it. Jesus asked, "Let he who is without sin cast the first stone." Many are out there doing evil and bad things, and hurting people. They just haven't been caught yet! They're no better than those who have served time in prison.

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A reader, anonymous, writes (25 August 2021):

This is verified as being by the original poster of the question

OP here—wanted to clarify—I am not sure I am in love anymore because I fear “What if the mindset and mentality behind those actions are still present today?” Even though he’s shown me otherwise, I am still somewhat paranoid, especially if he had done it for so long

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A female reader, ConfusedCarrie84 United Kingdom +, writes (25 August 2021):

Everyone has that one thing that is a deal breaker. It sounds to me that him having a criminal background is your deal breaker. It also sounds to me that all the info you have about him, comes from him. It sounds like he brags alot about himself, that is a concern. Unless others who know him that aren't family are telling you how great a guy bhe is then you can't really believe evwrything he says. You can take a leap of faith in him and see where that gets you.

You will never know if he is truly reformed until you are in a relationship with him.

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