“Should I Wait For My New Boyfriend While He’s in Jail?”

I have two small children, a boy and a girl, and I reunited with an old classmate of mine a couple months ago. He expressed his feelings for me, he took me to meet his parents, and they enjoyed my company, but there’s a problem. He is currently doing a two-year stint in jail for something he did when be was young. He takes full responsibility for what he has done. I honest to God love this man with all my heart and he loves me just as much, but I’m scared that he might get released and then move on from me. Should I leave him alone or should I hold on? Two years is not a lot. What should I do? — In Love with a Jailbird

If you don’t think two years is a long time: It is! Especially when you’re a single mom, waiting for a boyfriend in prison whom you can only see when you make the commute every other week to his jail), what do you think two months is? Two months is the amount of time you’ve been “reunited” with this old classmate of yours. In two months, you’ve decided that you “honest to God love this man” with all your heart and that he loves you even though you’re worried he’d ditch you as soon as he got out of jail? That’s not love. That’s desperation. That’s wanting to believe there’s something because it feels good to be introduced to parents and be told you’re important and that what you have is worth waiting for.

No good and decent man would ask a woman he’s only just reunited with to wait for him for two years and to remain faithful and committed to him for two years while he’s in jail. Come on, on some level you must know that. On some level you must know that he’s dreading his jail time and the only thing that makes it a little easier is the thought of someone waiting for him on the outside, sending him letters, calling him, boosting his morale while his life’s on hold. That he’s asked you — a single mom of two young kids whose time and energy and focus is already stretched thin by the demands of sole parenting–to make that kind of sacrifice is really effed-up.

And here you are afraid that you could make the sacrifice for him — while essentially putting your love life on hold — and that he’d ditch you as soon as he was released from prison, which suggests you don’t truly believe he loves you for you anyway. It’s more like he loves that you’re willing to be the support he thinks he needs while imprisoned. You’re willing to let him use you. Don’t be willing. Live your life and let him do his time, and if, when he gets out, you’re still single and he’s still interested, you can see where things go from there.

My boyfriend and I have been together for almost five years. For the last twenty months he has been incarcerated, and it’s been crazy difficult but at the same time liberating. I love him very much and have made the effort to make the three-hour drive to see him every two weeks. But I don’t know if I want to actually be in a relationship with him anymore. He will be coming home this December and I’m scared everything is just going to go back to the way it was before he went in. He talks about all these things he’s changed about himself, but I can’t seem to get over the past. I’m afraid that if I do break up with him, he’s going to do something crazy and ruin himself, and if that happens, I don’t know how I could live with myself. Any advice would help. — Wanting to Be Free


MOA. You’re over this relationship and you only do yourself and him a disservice to stay in it out of a sense of obligation. If it eases your conscience, you’ve already more than fulfilled any obligation you ever had as someone who cares for him by visiting him in jail every two weeks for the last twenty months. You’ve served your sentence along with him. Now liberate yourself and move on. Anything he might do after you break up with him is his responsibility. You can live with yourself knowing you were kind and good and loving for many, many, many months when so many others would not have made the sacrifices you did. You’ve done enough. You deserve to taste the same freedom he’s going to soon have.


Getting Personal: “My Life as a Prison Wife”
Updates: “My Life as a Post-Prison Wife”


Follow along on Facebook, and Instagram.

If you have a relationship/dating question I can help answer, you can send me your letters at wendy​(AT)​dearwendy.com.


  1. Anonymous says:

    Thank you. Your advice was very helpful. Thank you.

Leave a Reply

Your email address will not be published. Required fields are marked *