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Ask The Good Enough Guy: Is He Off-Limits ?


Will, about seven years ago, my sister dated this guy who was such a jerk. He was immature and very argumentative. He broke it off with her, and she said it was the best thing he could have done for her. She admitted to me that she wanted more out of life than just sitting around waiting for him to grow up. Well, recently this same guy and I crossed paths at a fundraiser and spent the whole night talking. He asked me out. My sister gave me the okay and “good luck”. So do you think I should date him, Will?  Could he have changed?


Old Dog, New Tricks?



Hmmm, this is an interesting question and not the first time someone’s asked it. This seemed like an easy answer at first, but there’s a little rat hiding in the question and it’s holding a trap. Let me explain where it’s hiding, and what I think you should do about it:

WHY YOU COULD DATE HIM:  When I was 17-years-old, I weighed 103 pounds (yes, seriously) and a hundred of that was mouth. I had the whole world figured out and couldn’t wait to get out and show my parents how wrong they were about life. Seven years later, I was 24 and a completely different guy. Four drill instructors and six years in the marines had taught me to shut the hell up, keep my head down and to get back to work. Seven years after that I was 31 and a completely different guy again; this time, a grown man, husband, and a father to a couple of kids who can’t wait to grow up and show me how wrong I am about life.

Who this guy was, who your sister was, and even who you were seven years ago means nada. Who is he now? Who are you? Are you two compatible? There’s one way to find out.

THE RAT: The problem isn’t this guy, it’s your sister. If you date him and he’s still a jerk, she gets to say, “I told you so” over a quart of chocolate ice-cream, no harm, no foul. BUT if he has grown up, and he’s a great guy now, and things start to develop between the two of you, well, that’s when the grits hit the pan.

Unless all three of you are VERY adult about the situation, there are going to be some hard feelings. Your sister may wonder if you always had feelings for him even when she was dating him. Soon you may wonder if your sister still has feelings for him and secretly wants him back. He may wonder, if you two don’t work out, he can have another shot at your sister. This whole situation is one bad weave and a torn t-shirt away from being a Springer episode.

SO WHAT NOW?  If you want my personal opinion (and I know you do since you wrote me), I say he’s more trouble then he’s worth. I have always had a rule about never dating friends of my family or family of my friends, and this guy falls loosely into the former. I don’t even like wearing my brother’s clothes; there’s no way in hell I’d date one of his ex’s.

There are literally millions of guys out there, why date one who has done, who-knows-what with your sister? If he wanted to date you, he should have asked you BEFORE he asked your sister out. Tell him no thank you, and then tell your sister that she was right about him because she was. Only a jerk would ask an ex-girlfriend’s sister out.

Seriously, even though this guy may have changed, he’s not worth taking a chance on screwing up the relationship that you have with your sister. Remember how mad she got when you borrowed her jacket and it looked better on you than her? Think about it.

Best of luck!
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William Jones is originally from the tiny town of Alton, Illinois, and now lives in the tinier town of Reisterstown, Maryland. He is a happy husband and a proud father of three, and writes as a hobby, in those few moments he finds between husbanding and daddy-ing.


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