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Wedding Woes

The issue is the lie

Dear Prudence,

I met this guy on an online dating site. We got along great and we’re into the same things. We’ve been messaging each other for almost five months but we haven’t met up yet. Turns out the guy is in jail! My friends and my family say I should drop him and find someone better but I feel a real connection with this man. What should I do?

Re: The issue is the lie

  • I would have a LOT of questions.  And they would remain unanswered b/c honestly 5 months is nothing and I wouldn't want to start to date anyone in jail.  It just seems like way more mess than I would be interested in.
  • Oh FFS.  Of COURSE you have a connection with him!  


  • Uhhhh. LW the fact that this is even a question means you probably have some internal shit you need to figure out. 


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  • 5 months. This is not some drunken disorderly stupid bullshit. This is someone doing real time. 

    Look, I've got more felons in my life than most people and I know that a criminal conviction does not necessarily make you a bad person, but I also know that being with someone with convictions is a tough road to choose. Also, the fact that this guy thinks now is a good time to be trying to date says a lot about his judgment. Let him go. 
    And maybe just maybe he's in prison because his personality is such that he's convincing?!? 
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