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We really like each other, but he dated my friend in high school? What should I do?

Tagged as: Dating, Friends, Troubled relationships<< Previous question   Next question >>
Question - (6 September 2013) 6 Answers - (Newest, 6 September 2013)
A female United States age 36-40, anonymous writes:

I've known this man since high school. We had casually talked and flirted while in school, and even after we graduated, but nothing ever happened. Then a few weeks ago, I happened to see him on a dating site I was on, so I sent him a message. We started talking and immediately clicked. Honestly, we go together like PB and J. He's everything I've wanted in a partner, and then some. So what could possibly be the problem? Well, he dated one of my close friends in high school. Now keep in mind, that was 6 years ago, but I'm still completely torn on what to do.

This friend and I have always had problems. To put it bluntly, she has jealousy issues. Our friendship almost ended a few years back when I was in a new relationship and started a new job, and she went in to a literal jealous rage because I couldn't see her as much as she would like. It was to the point where she would call me crying and sobbing because she would have to go a week without seeing me, and we ended up not talking for nearly a year (according to her husband this threw her in to quite a depression). Before this we were best friends and did do a lot together, but apparently she couldn't handle the changes that came with my life. Only just a few weeks ago have we started talking again, and it's still a very delicate situation.

So, she only dated this man for a short time. After all, it was only high school. I was only just starting to become her friend at the time, and as far as I'm aware they ended on so-so terms (not friends and haven't spoken in years). Here's my predicament: Do I pursue this relationship and risk completely ending the already unstable relationship with my friend? Or, do I risk letting go of someone who could potentially be an amazing boyfriend for a friend that I'm already on rocky terms with? Any insight is appreciated!

View related questions: best friend, flirt, jealous

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A female reader, anonymous, writes (6 September 2013):

personally she has a husbands, providing you don't date her husband then she has no right to tell you who you can or can't date. It was high school, a brief relationship. I may run it past her but not in a permission sort of way but like a guess who i'm going on a date with, you'll never guess who way etc. I didn't like him like that back then but since high school he has come on a lot, he could be someone special etc. Could tell her you came to her for tips, anything she remembers he likes/dislikes etc. What should you wear? She could help you plan an outfit etc etc.

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A female reader, eyeswideopen United States +, writes (6 September 2013):

eyeswideopen agony auntI totally agree with the Aunts, go for it, if your "friend" doesn't like it, tough. Your happiness should definitely matter to her, if she is truly your friend.

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A female reader, sugarplum786 South Africa +, writes (6 September 2013):

sugarplum786 agony auntGo for it. You both adults and she cannot be a factor in who you date. But seriously this friend has deeper issues, why would her not seeing you send her into depression? Her life and your life cannot revolve around one another. Its got be a friendship that is supportive not dependent.

Go with your heart, or you will regret the opportunity not taken.

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A female reader, CindyCares Italy +, writes (6 September 2013):

CindyCares agony aunt Pursue the relationship. If this frendship is so frail that it would be terminated by your " friend " seeing you happy, then it's a friendship you can also do without.

It was 6 years ago. It was high school. It was a short, not particularly life-changing relationship. Your friend is married now .

I agree with always tryng to be considerate of other people 's feelings- up to a reasonable extent, which do es not include giving up living your life because some egocentric , possessive " friend " may be bellyaching about it.

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A female reader, Got Issues United Kingdom +, writes (6 September 2013):

Got Issues agony auntI would go for it if I were you. Had she been single and possibly still holding a torch for him, then obviously no, but she is married, which basically means she has no say in whom he dates and whom you date.

If he is so great, and she is so jealous, then I think it would be preferable to lose her than him.

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A female reader, Honeypie United States + , writes (6 September 2013):

Honeypie agony auntYikes, this is a hard one.

Normally, I would say DO NOT date a friend's ex. It's just tacky. And specially not if you all run the same social circle.

She is married, which means she has found her "bliss". So with that in mind I would say, if you feel a strong connection I would go for it. She might not like it, but how can she hold a claim on a guy when she is (hopefully) happily married?

Have you mentioned that you ran into him? (to her) maybe that can gauge how she feels about it?

She sounds like a very high maintenance friend. One that takes more then she gives. I think I would talk to her, see how she feels - but honestly I wouldn't let her dictate who I date/see. It's been 6 years.

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