“Should I Wait for My Boyfriend to Get Out of Jail?”
I’m 28 and my boyfriend is 30 and about a month ago, he was suddenly and shockingly arrested. The details of his charge are extremely complicated, so I won’t try to explain everything, but he was caught in a sting operation. Since his arrest, he’s been held in jail. His lawyers advised him to not talk about his crime with anyone, which means he’s been unable to offer me any explanation for what happened. Even though my boyfriend has a clean record, his lawyers say the best plea deal they could get him would likely be 4-5 years in jail. Needless to say, this has been devastating and shocking news.
I love my boyfriend very much. He and I have been together for two and half years, and have been living together for part of that time. We were talking seriously about getting married, and I know he was even working on getting a ring. He has always been kind, caring, loving, and supportive; it’s beyond shocking to everyone who knows him that he could have broken the law.
It’s obvious his arrest caused major issues in our relationship (like trust), but I thought with counseling and time we could possibly overcome that. But now that I know that he could be in jail for four years or more, I’m not sure what to do. How could I wait that long for someone? How could we overcome the other major issues to our relationship with him in jail for several years? Would he even be close to the same person after that much time in jail? I want to do what’s best for me and him, but I’m not sure what that is. It seems like no matter what I decide, it’s going to be horrible and hurtful for everyone involved. — Arrested Love
It’s got to be incredibly shocking and painful to invest over two years in a relationship only to discover the person you thought you were with isn’t who you thought he was. I feel for you. But I also have to be a voice of reason. What will be even more painful than what you’re going through now is waiting on the sidelines for years for the chance of getting back the relationship you’ve now lost. The truth is that that relationship no longer exists, if it even ever did exist.
You may not know all the details of your boyfriend’s crime. You may not know who he really is, but you know he is NOT who you thought he was. And why — why, why, why — would you give up years of your life during your prime waiting around for someone you don’t even know? Because it would be too painful to break up?
People break up for painful reasons all the time. In fact, aren’t all breakups made for painful reasons? You aren’t right for each other, or your families disapprove of the relationship, or the timing just isn’t right, or distance comes between you, or someone cheated, or, or, … or one of you is guilty of a crime and goes to jail for years. It may be painful, but it doesn’t make it a bad reason to breakup. It actually sounds like a pretty sensible and logical reason to dump someone and MOA, particularly if you aren’t married, don’t have kids, have only been together a couple of years, are 28, and had no idea the person you were with was even involved in criminal activities.
I know it’s hard to let go of that image you had. But it’s already gone. That relationship you believed in never existed. Even the fantasy of it disappeared the minute you found out the truth about your boyfriend. Rather than try to build something new with him, you’d be better off building something new with someone else eventually — someone with whom you don’t have so much baggage to work through first, someone who isn’t in jail, someone you can let yourself trust.
If you have a relationship/dating question I can help answer, you can send me your letters at [email protected].


Wendy is right, you don’t know this person, you only know a false version of him that he has presented to you. Why wait 4 years for something that just doesn’t exist ?
LW –
I’ll tell you something about myself. I have been married for just over 2 years and have been with my husband for 6 years. When we got together, I knew he had a drug problem in the past (prescription drug abuse) and he had managed to get clean on his own. Fast forward 4 years: he loses his job, has trouble with his ex-wife as far as seeing his kids goes, and we get married 2 days after he loses his job.
Despite the fact that I was pushing him to get into counseling because I knew he still struggled every day with his addiction (he was clean thankfully, but that doesn’t make it less of a struggle), he made a very, very, very bad decision. He obtained a way to get some of the prescription drugs he was craving illegally and got caught (I won’t go into the sordid details).
I felt like you – the trust crumbled. So, its a little different with me because I KNEW this could be something that would happen because I knew he was an addict. You didn’t know anything of what was going on. I agree with Wendy, you probably don’t know who he really is. I had the benefit of knowing it could happen. Well, now my husband has been incarcerated for 16 months. Doesn’t seem like a long time, huh? Well, it is. A very long time to sleep by yourself. A very long time to explain to people why your husband isn’t with you. A very long time to take care of everything around the house while trying to worry about whether or not you’ll have gas money to go visit.
To be completely honest with you, LW, if we weren’t married when this happened, I wouldn’t still be with him. The vows I took are the reason I am willing to push through (that and I love his kids like my own). 4-5 years is a long, long time. And it hurts to hear it, but the likelihood of an unmarried man remaining with the person who sticks with him after he gets out of prison is pretty slim. Believe me, you DO NOT want to put yourself through what I’m going through. You don’t. It will hurt to leave him but for your own sanity and happiness, it may be the best option. If I could give you a list of all the ways this has hurt me (including personally, emotionally, professionally – I have a degree in criminal justice and being married to someone convicted of a felon hurts my job opportunities), it would take up this whole page.
Oh my, Honeybee! You seem to be getting along well, you’re a very strong woman. I’m sending love your way!
Thanks sweetleaf. It sure isn’t easy and I really wanted the LW to know that. I never in my wildest imagination could have forseen how hard it really would be.
From what you’ve told us, it seems as though your boyfriend wasn’t wrongfully arrested or even innocent. I’m not sure what type of crime he did that earned him 4 years with a guilty plea, but it must be something serious. The question you need to ask yourself is: Does this change who he is?
Another question you need to ask yourself is how much do you love him? You can live with anyone, you can talk about marriage with some people, but you can really envision your life with only a few (or maybe just one). Is he someone you can’t live without?
Just by you writing to Wendy, I have an inkling that you do feel that he’s changed and that he is someone that is disposable. Nothing wrong with that.
I was also wondering what he did to get 4-5 years with a guilty plea with no past record.
Honestly, LW, if I were in your position I would be pretty worried and constantly thinking…”If he can keep something of THIS magnitude from me, what ELSE has he been hiding??” If someone can hide a serious crime (worthy of being caught in a sting operation, no less!!) from his live-in girlfriend, what COULDN’T he hide?? Lying? Cheating? Bodies in the backyard?!
…Listen, I’m not saying your boyfriend is unhinged, but it takes cunning to pull off a lie of that magnitude. And if I were you, I’d be hightailing it so fast the other way, there wouldn’t even be time to consider staying with him. Love be damned…this guy is not the person you loved, anyway.
You make an excellent point. She is incredibly lucky to NOT be implicated in this whole mess, particularly since she lived with him. Who knows…maybe he really loves her and wanted to keep her “clean,” so he kept it all hidden. That doesn’t mean at all that she should stay with him; just speculating.
Someone who is very, very bad for you could love you deeply and passionately and earnestly. But-practically speaking-that doesn’t mean it’s a good idea to stick with them, or that you owe them anything in return for their love.
I agree she’s lucky. Maybe he did try to keep her free from any taint. But what if he’d made a mistake? What if next time he doesn’t manage to do so? The longer they are together, the less likely it is that he’d be able to keep her clear.
I know it’s hard to think of it this way, but your boyfriend proved himself to be completely unlike the person you probably thought he was. He’s shown that he’s capable of lying and deceit, he’s capable of being two-faced and having a secret life, and he’s capable of breaking the law, meaning he deals drugs, he stole from someone, he hurt another human being, etc. This is absolutely not the kind of person you want to build a life with and parent children with. And from personal experience, the guy who’s willing to break the law is the same guy who’s willing to cheat on you, lie to you, steal from you, etc. People like this lack a basic moral code that is fundamental for trust and you’re right not to trust him anymore. Whatever his illegal activity was, he chose it over a life with you. He 100% deserves to get dumped.
I don’t even want to touch the stuff about waiting for him. It’s besides the point. Even if he got out tomorrow, you should not be with this man. But as a military spouse who finds it extremely difficult to wait for her husband when he’s deployed, which is a noble reason to be away, I will agree with Honeybeenicki that you don’t want this life.
I do think it is somewhat bad for us to theorize as to his crime. There are many non-violent crimes that carry significant weight. He could be a murderer, or he could just handle paperwork/money for some very bad guys. None of it makes him particularly nice, but I don’t want to assume what he has or hasn’t done.
I agree about the speculation – we don’t know what he did wrong, which is what I find unfair with people claiming she doesn’t know him, and their relationship wasn’t real in any way. It could have been a white collar crime that he committed in the course of his regular (legal) job.
We just don’t know.
Ok, maybe my personal experiences were clouding my judgment a bit. But if he’s accepting a plea deal instead of pleading innocent, I have to assume that he knew what he was doing was wrong. If I had no idea I was committing a white collar crime, I’d want my day in court. Wouldn’t you?
It would depend a lot on what my chances of being found innocent would be. There are a number of people who are innocent – or at least who did not knowingly commit what they knew to be a crime – but take plea bargains simply because they fear being found guilty and getting a much larger sentence.
We’d like to think that only the truly guilty are sentenced and only the innocent go free, but of course that’s not always the case. A defense lawyer’s job is to minimize the probable impact on his or her client, not to defend the truth, and the lawyer’s recommendations might well be based on things well beyond the actions and intent of the boyfriend.
You might think you’d want your day in court, but your lawyer would quickly disabuse you of that notion. White-collar crimes are some of the easiest for prosecutors to prove, because everything’s on paper. Many, many crimes do not require that you intended to break the law, only that you intended to do what you did (i.e., it wasn’t a literal accident, like you accidentally drew an x on a form and that’s now being taken as a signature), and that that action was illegal. So at that point, you’d basically be depending on a jury to be like, Aw, this person didn’t mean any harm!, despite the law, the judge, and the prosecutor telling them conviction is appropriate. That’s very unlikely to happen. However, if you plead out, you are going to get a much, much, much lower sentence than what you will get if you went to trial.
There are a lot of good points in here, especially about his future employability. And I agree that accepting a plea deal means they had some pretty solid evidence against him. At best, this boyfriend has terrible judgment (which is not to be underestimated… terrible judgment should be a deal-breaker) and she should not marry him. At worst, he is a two-faced criminal… and she should not marry him
Another question to ask yourself is, do you want children with this man? You’re 28 years old now, he still has to go through his trial and sentencing, and then has to serve 4-5 years. So you’re looking at being 33 or 34 when he gets out. And then there is the time it takes to rebuild your relationship and get to know each other all over again. Then you’re looking at being 35 or 36 before you started trying to have kids.
There is nothing wrong with people who decide to have children later in life, but is that what you want? If it is, you should know that it’s harder to get pregnant the older you get, and the farther past 30 you go, the chances of complications during pregnancy increase.
If you are ok with waiting that long, or if you don’t want children, that’s perfectly fine. But, it’s something to think about when deciding whether or not you’re willing to wait for this guy.
He could return a very different person and WORSE, too…
Adding a PS: I suppose there are white-collar crimes (less horrible sounding than drugs or prostitution rings) which could be subject to “sting” operations, too … so I should acknowledge that possibility. I’m not sure this changes the substance of my post, though.
Agreed. Even though white collar crimes are not as violent or “dirty,” they still involve theft and deceit. Money laundering doesn’t sound as bad as drug trafficking, but it still requires a weak moral compass to commit such a crime. And do you really want to marry/date someone like that? I know I don’t.
LW, the issue is your belief that he is the guy you’re going to marry. But you don’t have to be afraid of losing your “one”. There are men out there who will love you as much, if not more than your current boyfriend and that’s okay. It’s not okay for him to hide another part of his life, essentially hiding a part of himself. This is what you don’t like, I am guessing. You don’t know what else he has left to hide, you don’t know about the case, and you don’t know about your obligation as a partner in this relationship. But as rational readers who try to make logical conclusions, we know some things too.
We know that what he’s hidden isn’t worth 5 years to find out. We know that this can be a coin toss against your reputation, social circle, and life opportunities if you risk attending a trial for a crime you probably don’t support. We especially know that as a partner in this relationship it is okay to be scared, and it is okay to want to leave because you don’t know and are not sure if some one is worth 1825 days of your young life. You literally have one life to live. All of us do. And if you are comfortable spending 5 years in an emotional limbo wondering, waiting, then so be it. But don’t be that person who waits, expecting the same grandiose relationship you may have started out with— expecting to continue where you left off. Because frankly your relationship will never be the same once he gets out. His life will change drastically in terms of career, friends, and life opportunities, but so will yours. Your own future and future dreams will be in jeopardy.
Are you willing to live with that?
I think if ANYTHING.. you are lucky you haven’t married him. you avoided a HUGE disaster.
I’m sorry, but I think you should move on. I can’t imagine your 2.5 year relationship withstanding this.. and I don’t see why you’d want it to.
First of all, you are innocent until proven guilty in a court of law. And for all we know, he could be innocent. It’s unlikely, but possible. If he is innocent, the LW would probably feel guilty for abandoning him, and this is a possibility she must weigh.
However, if he truly is guilty, he lost the right to be in a relationship with you. He screwed up. He must admit this. A good man would let you go free and not make you feel guilty about it.
You’re dating a very dishonest man. To you, to the law, etc. Why would you wait 4 to 5 years for someone who disrespected you to that level and put you in DANGER of being classified (possibly) as an accessory to whatever crime he’s committed, or “harboring a fugitive,” etc.?
You deserve better than that.
LW, you don’t get into the nature of your bf’s crime. But if it was so bad that the cops performed a sting operation to catch him, and he’s facing *years* in prison, he must have been up to some pretty crazy shit. And hiding it from you. His arrest and jail time aside, would you want to be with someone that committed terrible crimes and basically led a second life while in a relationship with you? Wendy is right- the person you thought you loved never really existed.
It seems as though there is a push to know whether or not your boyfriend is guilty, and that it will be a factor as to whether you may stay with him or not. This is exactly how I would feel as well. It he is innocent, it means he didn’t create this situation fully knowing how much it could hurt you, if he isn’t well, he is not worth your time.
Here’s the thing. If he takes a plea deal, that means he’s telling the court, and you, that he’s guilty, whether he really is or not. Instead of trusting his innocence to get him a fair trial, he is putting your life together on hold for years because he is afraid of the outcome. I can’t even begin to know what I would do in his place, but I think that if I were really innocent, no way would I go to jail for years instead of seeing my trial through.
Don’t wait for him to tell you what happened, because he will most likely just tell you what will convince you to stay with him anyway. Instead, trust his actions. If he pleads guilty, he is and does not deserve your devotion for damaging your lives together so irresponsibly.
LW – I work at a community college in a fairly urban area. I teach business writing and I also serve as a tutor. I have worked with many students, in the capacity of teacher AND tutor, who have been incarcerated for varying periods of time. One student in a business class talked in a reflection paragraph about having to explain at interviews about the incarceration, and how it had made him virtually employable. Other students have written about how different they were when they came out, how they have a “jail mentality.” In some cases they served longer than your BF is looking at potentially serving, but in many cases they served 2-4 year sentences. I can’t speak for your boyfriend with certainty, but I can speak from my own experience that jail does change people. Even if they don’t come out more hardened, they still come out with a different mindset. They’ve been in a place where their every action is monitored for years. They will experience depression, frustration, anger when they are released and can’t find work. They find themselves shunned by family and former friends. They become isolated. I’m not going to tell you that you have to MOA, but I am going to tell you that the man who comes out of jail will NOT be the man who went in, and that only you can decide if waiting to figure out whether you can love that man is worth it.
You mean “unemployable”
Keep in mind that you don’t have to decide immediately.
I think it come down to was he innocent or was his offense forgivable? You can’t know that until he’s able to talk about it, after the trial.
If you love him and you can forgive him, stick with him. If you learn that he did something terrible, maybe he’s not the guy you were in love with.
If he can’t tell you the details of his situation, then you have to move on. I couldn’t imagine going through this without knowing exactly what he did. I wonder, though, how long ago this crime took place. If it happened when he was in his early twenties and he’s just now getting caught, it’s a much different story.
Read “Orange is the New Black” by Piper Kerman. At least read the beginning. It’s about a woman who committed a crime when she was in her early twenties and wasn’t caught until a decade later. Her fiance had absolutely no idea she ever had a shady past. She was only in jail for a year, but he stayed with her. Of course, she also told him all the details about what she did… so…
I don’t have any advice for the LW. And even though the whole world is against him, I have some sympathy for the boyfriend (I know, I know, he’s a bad guy, in jail, all that stuff – but he committed a crime, got caught and will pay for it for the rest of his life. that should be punishment* enough, in my opinion). The guy lost everything, and his life is on hold for the next 4-5 years.
He knows he did something that impacted her life, and if he does love her, he knows he has no right to ask her to put her life on hold for him.
I think that the LW has the right mindset. And I hope she follows all the advice here. My only suggestion is to be there for him emotionally, at least now, in the beginning of his sentence. You may be his only lifeline.
So LW, take it slow. Like Black Iris said above, you don’t have to break up with him right away. You’re probably still in shock, and it’s completely understandable. One month is not nearly enough to process what happened and understand future implications.
However, I hope you can find it in your heart to provide him with some emotional support for a little while (1-2 months), but at the same time, have one foot out the door. If you can’t be there for him though, no one will blame you.
*I take all that back if he was trafficking minors.
Some of the other commenters seem very eager for you to leave him behind, but honestly if it were me, I’d wait until everything is legally settled. I’m assuming if there’s a plea, the legal proceedings will be over in the near future. Then you’ll be able to give him a chance to explain and also know how just long you’ll be waiting. And depending on the situation of the crime, he may be able to explain to her satisfaction.
I’m not saying you should stay with him by any means, but I am a big believer in waiting until things cool down and all the facts are known to make decisions.
I’ve been away and just now catching up, and apologies if someone else brought this up already. Did anyone else flash back to that letter from a couple of months ago where the BF would disappear and his family members were arrested and sorts of shit was going down. I couldn’t help but think immediately that this was an update of that!
At any rate, I think you’ve gotten some good responses here, being taken much more seriously than that other letter I referred to.
I had been with my boyfriend for three years when he got sent to jail for one year. It was so hard to be myself for a whole year, driving six hours every weekend to see him, only getting to speak to him for five minutes a day. Anyway after a year he got out and decided that he did not want to be with me anymore. Please don’t waste your time like I did, if your meant to be together in the end then maybe you will but don’t waste your life being lonely and waiting for him. Men who go to jail and expect their loved ones to be there for them are very selfish people.
I’d say sticking around for a jsilbird is NEVER a good idea…
Anyone else running all the scenarios of what it is he could have done?! It’s kinda crazy. I’ve often wondered if we ever *really* know who someone is behind closed doors.