I have a problem that I need help with. I have been recently hanging out with some one who I known for 12 years now, we have a great friendship. Recently we have been flirting with each other and I really like him. I’m interested in taking our friendship to the next level. He does not know how I feel, but that’s not the problem. The problem is that he is my sister’s ex-boyfriend. They dated 12 years ago for about a year. She cheated on him which was the reason why they broke up. He has stood close with the family ever since. Now my sister has been married for the past 6 years and has kids with her husband. I really think that we would be very compatible together, but I don’t know how the family would react if we started dating.

What should I do? Should I follow my feeling and tell him how I feel, or should I keep it to my self? I don’t even know how my family is going to react if we do start dating. We are very close as a family and I don’t want to stir up trouble . I also don’t want anyone to feel awkward because of me. Please help.

Signed alone and confused.

You can find this letter on Strawberry Letter archive.

Dear Alone and Confused,

Question…. Why are you hanging out with your sister’s ex in the first place?  That’s a bit odd, at least for me.  Furthermore, why is this guy still hanging around your family?  He had his chance, and he didn’t make the cut.  Now he is flirting with you.  I’m a bit suspicious of this guy.  Your sister has gotten married and moved on with her life, and this ex is STILL hanging around??

Anyway, would you really want to kiss a guy who also kissed your sister?  I wouldn’t.  Sisters have boundaries, a special code.  This is also true for friendships.  Girl Code 101: Never date your friend’s (or sister’s) ex.  Trust me when I say it brings up all kinds of weird feelings.  In college, one of my friends dated my ex behind my back.  When I found out and confronted her, she told me that she did not see anything wrong with it and was not going to stop dating him.  Our friendship ended because of it. I felt so betrayed and angry.  It put our mutual friends in a awkward situation.  They felt like they had to choose between hanging with me or her.  You don’t want that to happen between you and your sister.

So you have a few options:

  1. You can NOT date him and keep things platonic.  Better yet, don’t hang out with him at all.
  2. Date him without talking to your sister first.  This is depending on if he actually wants to date you.  He may just want to keep things light and flirty.  OR… he may just want sex.
  3. Talk with your sister first, privately.  If she says she is not ok with it, you have to respect that.  Your sister is your family.  This ex is not.

*Something to think about.  If you do date him and things do not work out, then what happens?  Will he still come to family functions since he is close to your family?  He didn’t stop hanging out with your family after your sister dumped him.  Will you be ok with him coming around your family even though things did not work out?  Family gatherings will become very weird and uncomfortable.  Plus, ask yourself what type of man has no problem dating sisters?

I would just leave this guy alone.

Good luck to you.

~Jana Leigh

If you have a question you would like for me to answer, please contact me at AskJanaLeigh@yahoo.com.  I love getting your emails, so keep them coming guys.

Photo credit: songwriterumbrella.com

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