Sharing Your Sordid Past

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Dear Bitter Single Guy: I, for the first time, have not only broken into the world of cyber dating, but have been chatting with a girl who I really like (as far as I can tell).This has been going on for a couple of weeks now and we are talking about actually meeting.

Problem is; I have a rather sordid past. I’ve been to prison, I don’t have a driver license and I’m married to a woman I haven’t seen or heard from since 2 months after the wedding; just to name a few. Having said all that, I am not a bad guy, I’ve just made some bad decisions. My dilemma is; when do I come clean? I know that I have to tell her all of this and more, but I don’t know when. Do I do it now and risk never meeting her? Or do I try to slip her little bits at a time, and hope she absorbs it all before she figures out I am/was a loser? ~Don’t Want to Screw Up~

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Dear DWSU: The Bitter Single Guy believes that everyone deserves a second chance (third, fourth and fifth chances are also appropriate), so he is pleased that even after some bumps in the road, you’re back in the saddle.  Weirdly, the BSG (grammar geek that he is) is also pleased by your use of “driver license” (people…it’s only a license for one person and the possessive is silly…would you say “certificate’s of achievement”?) The BSG is a little embarrassed by this tiny rant (rant-let), but he’s letting it stand.

DWSU online dating is problematic for many reasons, not the least of which is that you’re not yet dealing with the entire person. You’re working with a picture, a profile and (if you’re lucky or focused) a phone call or two. Although it’s entrancing to believe that this is the whole picture, the BSG wants to remind you of what you, in your non-attracted-to-someone mind know: that your Delectable Dandelion isn’t quite real until you have a chance to interact in person. (Readers who have had long, successful, exclusively online relationships are shaking their fists at the BSG right now, but he doesn’t care. If you haven’t met in person, you’re pen-pals.)

But the BSG doesn’t want to minimize your situation. You’re right to balance the fact that this relationship is new and just like a new baby bird out of the shell; it’s easily crushed. On the other hand, anything perceived as deceptive now could be shake the foundation of the relationship if it lasts.

Here’s the BSG’s advice. Prior to meeting Delectable Dandelion, tell her that you’re in the middle of correcting some mistakes you’ve made in your life: mistakes that unfortunately resulted in you spending some time in jail recently. (the BSG recommends the use of the word “jail” over “prison” because while he knows there is a difference, “jail” is likely to sting less. Heck…the Dukes of Hazzard were in “jail” all the time and those guys were just fun-loving goofs. “Prison” is featured in much scarier TV shows and movies.)

The BSG thinks that’s enough pre-information before you meet. The BSG then recommends meeting in person and enjoying each other’s company over a cup of coffee or something equally festive.  AFTER that first date, the next time you meet in person, the BSG recommends a somewhat deeper conversation about the depth of your sordid past. This will give Delectable Dandelion a solid non-scary experience (the aforementioned festive coffee date) to balance against the new information. While you’re correct to want to be honest, and also correct in your fear that this may scare Delectable Dandelion away, the BSG wants you to balance the frequency and amount of sordid past information with festive date-time in order to ease her into the truth. This is the equivalent of not taking a dish right out of the fridge and putting it directly in the oven. Usually that results in the dish shattering (although the BSG knows that Pyrex is typically safe in this situation, so few people are made of Pyrex these days).

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