I am now 32, and I have always thought about him and wondered what our lives would have been like if he hadn’t been locked up. He’s been on my mind so much lately that I found his profile on a website called loveaprisoner. Should I reach out to him? It looks like he will be getting out relatively soon. I don’t want to be duped again if he hasn’t been rehabilitated, though. Any advice you give is greatly appreciated. — Missing The Jail Bird
Eleven-plus years is a long, long time, especially considering you only dated a few months, you haven’t been in contact this whole time, and you have no idea what this guy might be like after spending over a decade locked up. (Here’s one story, written by a DW reader, of some of the challenges she faced when her husband was released from prison. It was hard for them and they had the benefit of a strong relationship and regular contact while he was in prison, two things you do not have with this man).
If you decide to reach out to this guy, you certainly need to manage your expectations and be clear to yourself what your motives are. It’s easy, especially when we’re lonely or it’s been a while since we felt a true connection with someone, to romanticize someone from our past. But this guy has, for all intents and purposes, been dead to you for a long time, and you know what they say when someone you love dies? Their flaws suddenly disappear. I’m sure this man had flaws. And for all you know, they may be deeper and more intense after all these years he’s been in jail. He will likely face challenges in readjusting to life on the outside that will make investing in a new relationship a near impossibility — at least for a while.
I would only recommend you reach out to this man if you can do so with the intention of only being a friend. But when you use language like “I don’t want to be duped again,” it seems like you’ve already decided what kind of relationship you want with him and, if he fails to meet your expectations, you’ll be angry. Spoiler: He’s probably going to fail to meet your expectations if you try to rekindle a very short relationship from a decade ago at this juncture. If, a year after he’s been released from jail, you’re still thinking of him and wondering if there might be something between you worth exploring, by all means look him up. But keep in mind that he may very well not be the man you remember. The truth is, the man you remember may never have existed.
If you have a relationship/dating question I can help answer, you can send me your letters at firstname.lastname@example.org.