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I Had A Creepy “Date” With The Guy My Sister Is Now Dating – Daily Dilemma


Here is Today’s Daily Dilemma:

Hey Guys,

So here is my dilemma. About a year ago I was on a dating site, I was mostly into meeting new people and figured well, if I met someone really great, well that’s a bonus. That didn’t happen but that could be another story.

One of the guys I did meet though I met for lunch. There was no attraction which was fine as I was just looking to meet new people, during our lunch I explained that and was happy to have met him etc. Long story short the guy got really creepy and needy after that. He sent me some very sexual and suggestive texts and just would not understand that I was not interested. After a few of these types of exchanges and my eventually ignoring him, he stopped and I never thought about it again.

Fast forward about a year and guess who my little sister brought over to meet the family during the holidays?

I did not get the idea that this guy remembered me, or he played it off well but it was really hard for me to not say anything to my sister, I didn’t want to ruin her Christmas and New Years but now I am wondering, do I say something to her or do I just pretend I just the met this guy too?

The “Daily Dilemma” on the Sean and Richie Show is featured every weekday morning at 6:40am. We and the listeners take on someone’s problems and try to offer different perspectives. Now, these don’t have to be huge problems- it could just be something bothering you or a friend, or it could be some little thing you and another just can’t agree on. If you have a dilemma to share we’d love to hear it just e-mail us here at the show.

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